Key West Yacht Rentals - Private Charters & Cruises

Experience the yacht lifestyle on the Mia in beautiful Key West, FL.

vacation yacht rentals key west

Mia Yacht Key West

Key West Yacht rentals is more than a brokerage service. We are a wealth of local knowledge with superior service to ensure your Key West Yacht experience is one to remember. We love making new friends and creating awesome memories. The MIA is a well-appointed 90 ft Cortenzo yacht built in 2009 and completely refitted in 2020. It is berthed at beautiful Stock Island Marina village with all its great amenities. The MIA with its 4 staterooms beautiful salon and comfortable media center is cozy comfortable which lends itself to all that Key West and its beautiful water offer. We pride ourselves on building custom packages for all our guests. Our attention to detail is paramount in allowing you to sit back and relax and enjoy all that Key West and its surrounding unique lifestyle.

The Mia - Key West Yacht Rental Photo

The Mia Services

All cruises are BYOB for alcoholic beverages, food or snacks. A chef can be provided if desired to prepare your special meal, additional info and cost will be provided upon request. Full galley, grill, coolers, ice, bottled water, sodas, glasses and place settings, utensils, blender, and crew is provided. ​Sunset times vary throughout the year, for times available click please send a request for your desired dates.

All cruises and routes are subject to change due to docking, weather or current conditions, USCG restrictions or Captains' discretion.

vacation yacht rentals key west

Take A Video Tour

The Mia Yacht in Key West was a wonderful experience for our family, beautiful memories were made. Top notch service, would highly recommend to anyone. A trip out to Boca Grande Island is a must if you’re visiting...The atmosphere of Stock Island Marina was amazing, lots of amenities. Truly a wonderful place to gather on any occasion. We definitely will be returning.

Best Day Ever!! Owner Mike and Captain Ryan and crew are the pinnacle of service and professionalism. If you like 1st class service and beautiful accommodations, Mia is the boat for you.

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The Mia - Key West Yacht Rental & Charters

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How to rent a yacht in key west, find the perfect boat.

Enter your desired location and date to explore our fleet of yachts.

Select a captain

Choose to drive yourself or select a USCG licensed captain.

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Connect with your boat owner and complete your booking online.

Enjoy your day on the water with friends and family!

Why Boatsetter?

As the global leader in peer-to-peer boat rentals, Boatsetter offers an easy, safe and accessible way to experience on-the-water adventure. With boat rentals in 600+ locations, finding a boat is easy and with the option to tap into the largest network of USCG licensed captains, boating experience is not required.

Boating with Boatsetter

Get out on the water worry-free, knowing our insurance covers every boating trip

Choosing the right boat rental platform is essential to your peace of mind while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

Got questions?

Frequently asked questions

What makes Boatsetter different from other boat rental platforms?

What makes Boatsetter different is peace of mind. Boatsetter is the first and only boat rental marketplace to offer insurance on every peer-to-peer boat rental. We know choosing the right boat rental platform is essential to your experience while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

How to rent a boat on Boatsetter?

At Boatsetter, our mission is to make getting out on the water as easy as possible. With our intuitive booking system, you can rent a boat as soon as today. -First, you must determine your budget and the type of boat you want to rent. -Next, decide where you would like to boat and the kind of boat you would like to spend the day on. -Finally, determine if you will be needing a boat captain and reach out to the boat owner. That’s it! You’re officially on your way to a fantastic day out on the water.

How much does it cost to rent a boat?

The cost to rent a boat depends on whether you are renting for a half-day or a full day, the boat features and the boat size can impact your boat rental price. Rental prices can range from $200 to $1,000 plus depending on the boat rental itself and the length of time of the rental.

How many people can fit on the boat rental?

The number of people who can fit on boat rental largely depends on the boat’s size and how many life jackets are on board. Currently the coast guard allows a maximum of 10-12 people on a Boatsetter boat rental.

How much does it cost to rent a yacht?

The cost of renting a yacht depends on the boat’s size and the amount of time you’ll use the yacht. The onboard amenities and luxurious accommodations also dictate the price. You can contact our yacht specialists for a custom quote by visiting https://www.boatsetter.com/luxury-yacht-charters .

How old do you have to be to rent a boat?

You must be 18 years old to rent a captained boat and 25 years old if you would like to rent a bareboat charter.

Do I need a boating license to rent a boat?

Boating license requirements vary from state to state. As a renter, you are responsible for understanding local state requirements.

Can you rent a yacht for the day?

Boatsetter allows you to rent a yacht for the day. Single-day yacht rentals are available for a select number of yachts. To chat with a yacht specialist please visit https://www.boatsetter.com/luxury-yacht-charters .

Can you rent a yacht for the week?

Boatsetter allows its customers to rent a yacht for the week. Renting a yacht for a week gives you more access to the wide range of yachts available on our platform. You can either book a rental directly through the site or connect with one of our charter specialists to plan your trip here: https://www.boatsetter.com/luxury-yacht-charters .

Can you rent a yacht for the month?

Booking a month-long yacht rental is a detailed and hands-off process when working with our team of yacht charter specialists. We tailor each yacht charter to our client's specific wants and needs. Our luxury yacht charter specialists can be reached at (954) 715-4114 or by visiting https://www.boatsetter.com/luxury-yacht-charters .

How to rent a private yacht?

Renting a private yacht is a very detailed experience that caters to your exact needs while onboard one of our luxury yachts. To plan your private yacht rentals experience please visit https://www.boatsetter.com/luxury-yacht-charters .

How much does it cost to rent a pontoon boat?

The cost of renting a pontoon boat depends on the size, location, and rental time of the boat. Prices can range anywhere from $200 for a half-day rental or just under a $1,000 for longer rentals.

How much does it cost to charter a yacht?

The cost to charter a yacht varies depending on the boat size and the length of the charter. Prices typically range from less than $1,000 to $5,000 plus if you’re wanting to charter the yacht overnight.

How much does it cost to rent a boat for the day?

The cost of renting a boat for the day on average ranges from $200 to $1200. The cost to rent a boat varies depending on the size of the boat and the length of time that you will be using the boat.

How does the boat insurance work?

Boat insurance typically covers loss caused by things such as fire, sinking, storms, and collisions. The extent of the coverage varies depending on the policy.

Do I need my own insurance to rent a boat?

You do not need boat insurance when renting with Boatsetter. Coverage is provided under the Peer-to-Peer Boat Rental Policy, which is underwritten by GEICO Marine Insurance Company. The policy was written from the ground up as a stand-alone recreational boat rental insurance policy covering the period of time that the boat is being rented and is available for all non-commercially insured boats.

Does Boatsetter screen renters?

Yes. We use a system called Cognito to ensure that payment information matches the renter's identity. We also require renters taking out a captained boat to be at least 18 years old and on a bareboat to be at least 25 years old.

Is listing my boat on Boatsetter free?

Yes! Listing a boat is completely free. We only take a commission when your boat is rented. We only make money when you do!

What if I'm not comfortable having a renter drive my boat?

If you are not comfortable having a renter drive your boat, we have an expansive network of licensed and experienced captains. Once your boat is listed, you can filter through our network of captains and favorite captains in your area that you would like to operate your boat.

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Top yacht rentals reviews in Key West, FL

vacation yacht rentals key west

The Happy Prince...

Very nice !! Beautiful boat Well maintained .Ryan was great captain with great local knowledge of the keys...

vacation yacht rentals key west

48' SAILING...

Fantastic!!!! Tim and the Captain went above and beyond.

vacation yacht rentals key west

Ryan was an excellent captain. Great attitude with keen local knowledge that made our day at Boca Grand a total success.

vacation yacht rentals key west

Luxury 45’ Sea...

Tim was very helpful with the reservation and made it very easy to plan for the day. Chris was a great captain and...

vacation yacht rentals key west

Our Captain, Jason, and his Co-Captain were amazing!! They were both very knowledgeable about the area and took great...

vacation yacht rentals key west

Duet - 2023...

We had a group of 12 people (plus 2 captains) and fit very comfortably on the top/main part of the boat. It was...

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40' Luxury...

Incredible boat! The best way to see a Key West sunset. Lots of room onboard, great table set up for gathering....

vacation yacht rentals key west

We had a great day - thanks to Tim for all the communication before our day - ordering provisions was a home run too!...

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Both Brian and Patrick operated the boat and were outstanding hosts to our full family.

All of us were very...

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Boatsetters works like a charm. Great communicaton from the booking agent Tim in Key West thru to the boat owner and...

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We had great day. The boat was in good shape and Captain Dan was awesome.

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Yacht Rentals in Key West, FL

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  • Key West Fishing Charters
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Key West Charter Boat

Book Key West Yacht Charters

   Key West yacht rentals are the very definition of luxury. Whether you’re aboard a 45-foot catamaran cruising Key West harbor or sailing the entire Florida archipelago to Key Largo on a 200-footer, every comfort and amenity is provided. From family vacation Key West Sunset to corporate retreat, there’s a size and design of yacht that’s perfect for your needs.

   Call Key West Charter Boat or fill out a quote form. We’ll make all of the arrangements for a boating experience you and your guests won’t soon forget.

Catamarans & Motoryachts

   If you’re looking for a luxury cat, you’ll find a wide variety to choose from, with hull lengths ranging from 38-feet to over 65. A sailing catamaran’s unique combination of roominess, stability, and speed make it the number one yachting choice in the keys. Cats are available in both sail and power versions with our Florida Keys yacht charters. Both are fully outfitted for luxurious cruising, including air-conditioned salons and berths, multiple heads with showers, and fully-equipped gourmet galleys.

Charter QUOTES

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Charter Type Charter Type Yacht Charter Deep Sea Fishing Charter Flats Fishing Charter Sailing Charter Large Group Charter Private Custom Charter Sunset Charter Overnight Charter Boat Rental Dry Tortugas Charter Cuba Charter Jet Ski Rental Spearfishing Charter Snorkeling Scuba Diving Glass Bottom Boat Lobstering Charter Dolphin Watching Corporate Boat Party Wedding Charter Film Production Charter Other

Duration Duration Half Day (4hrs) 3/4 Day (6hrs) Full Day (8hrs) Multiple Day

Number Of Participants Number Of Participants 1 2 3 4 5 6 More Than 6

Location Location Key West (Lower Keys) Islamorada / Marathon (Middle Keys) Key Largo (Upper Keys) Dry Tortugas Cuba Other...

Date(s) Of Charter

a rental hangs out at a local sandbar with Key West Yacht Rentals

The Ultimate Florida Keys Vacation

A catamaran’s wide beam and versatility make it the perfect key west boat rental for family vacations. With so much room for storing paddle boards, snorkeling equipment, kayaks, and inner tubes, everyone can bring their favorite form of fun. A cat is also the ideal platform to throw a sunset cruise party for friends and colleagues, with room for over 30.

Whether you bareboat or hire a captain and crew for our day sails, you’ll discover the greatest luxury of all is freedom. When you sail from Key West on a private yacht, the world falls away in your wake, crowds become nonexistent, time gets lost in the waves. It’s just you, your party, and the wide-open sea.

From horizon to horizon there’s an entirely new world to discover, one filled with wildlife and adventure. To port, a flight of pelicans might be skimming the white caps in search of a meal. On your starboard side, dolphins play a game of hide and seek, popping up here and there, eliciting shouts of joy from all on board. With every mile sailed, the stresses of work evaporate in the tropical air.

 Entertain On A Key West Yacht Charter

If ever there was a perfect setting for entertaining clients, it’s on a motor yacht in South Floridas Key West. Take your most valued customers on a sportfishing excursion and let them test their skills on the deck space and in the fighting chair. The Florida Straights are famous for Sailfish, Shark, Black Fin Tuna and a dozen other species of fighting fish. With the warm waters of the Gulf Stream flowing between the keys and Cuba, the area offers some of the best angling in the world.

Sport fishers can be every bit as luxurious as cruising yachts, with all of the amenities your clientele would expect, including leather and teak furniture, state-of-the-art entertainment systems, carpeted salons, full bars and more. Just say the word and we’ll have a private chef aboard, ready to turn the catch of the day into a platter of the freshest sushi imaginable.

Corporate Event Charters & Parties

Key West yacht rentals are the go-to choice of experienced corporate event planners around the country. There’s something about tropical breezes and the motion of water that just can’t be equaled by hotels or convention centers. Hold your next outing of friends and families on a multi-deck luxury yacht and it will be hard to go back to land-based events. Whether it’s an elegant dinner cruise, a company awards ceremony, or fun-for- all jet ski party, the versatility of an ocean-going yacht is unmatched.

Call Key West Charter Boat or fill out a quote form. With our wealth experience and local knowledge, we’ll make the entire event effortless, from arranging on-board entertainment and catering to setting up water sports activities. All-inclusive packages are available on yachts that accommodate up to 300 guests, or as few as ten.

a boat on charter cruises with Key West Yacht Rentals

More Yachting Info...

Yacht charters reimagined.

A Key West yacht charter takes you to some of the most beautiful aquatic environments in the United States. Designated a national marine sanctuary, the lower Florida keys host an almost limitless variety of fish, birds, and mammals. Anchor your rental boat at one of a thousand secluded spots and spend an afternoon snorkeling or scuba diving among the brightly colored tropical fish.

Seven miles south of Key West you’ll find the world’s third-largest barrier reef, with its own unique underwater ecosystem. A short sail up the island chain will bring you to Bahia honda key, where miniature key deer can be seen roaming the state park. As their name implies, miniature key deer are native to the Florida Keys and found nowhere else in the world.

Key West Yacht Scuba & Snorkel Charters

If it’s an adventure you’re looking for, have the yacht’s captain take you to the many shipwrecks located all around Key West. Some lie in shallow water and are easily reached by snorkelers. Others will require scuba gear, like the USS Vandenberg.

A former World War II troop transport ship, the Vandenberg was scuttled south of Key West in 2009, forming the second-largest intentionally sunk artificial reef in the world. Rising from the seafloor 140 feet down, the superstructure of the Vandenberg lies just 50 feet below the surface, making the wreck accessible to nearly all levels of scuba divers.

Florida Keys Destinations Untouched

70 miles due west lie the Dry Tortugas, a group of islands first explored by Ponce de Leon in 1513, and one of the most popular destinations for Key West yacht rentals. So impressed by the abundance of sea turtles in the area, Ponce de Leon named the islands Las Tortugas , The Turtles. (“Dry” was added later when it was discovered the islands had no fresh-water springs). On your own private yacht charter, you can explore Las Tortugas’ famous coral reefs and sandy beaches at your leisure.

Designated a national park in 1935, special permits are required to camp overnight on the islands, but day trips via ferry or private yacht are easily made from Key West. While Ponce de Leon never found what he was looking for (The Fountain of Youth), you’re sure to discover the restorative and relaxing powers of the islands’ aqua blue waters and radiant sunshine. And when you’re here, don’t forget to visit Fort Jefferson, a massive fortress built by the Army Corp of Engineers years before the Civil War.

Key West Yachts Fully Provisioned

Located between the Gulf of Mexico and the Atlantic Ocean, Key West is the perfect staging point for voyages both short and long. Provisioning your yacht for a cruise is simply a matter of visiting the local supermarkets or sending a shopping list ahead of time. Your boat will be fully stocked and ready to go when you arrive, allowing you the freedom to get underway quickly and easily.

If you are bareboating, allow time for a full review of the boat’s operation systems, including sail handling, docking procedures, navigation and communication equipment, and all safety gear. Plan on a couple of hours for this very important portion of your trip. Experience in sailing boats of equal size and type is required, so don’t forget to bring the appropriate licenses or certificates, if applicable.

Gateway To The Caribbean

Located so close to the Caribbean, it’s not uncommon for Key West yacht rentals to visit international ports of call. Head southwest and the Yucatan peninsula is a week charter. Due East lie the Bahamas. From there it’s a game of hopscotch, island to island, country to country, down the Caribbean archipelago.  Near or far, if you bareboat, you’ll need to file a sail plan with your charter company, including all ports you plan to visit. Of course, changes can be made en route so long as you keep the company notified.

Key West is one of the most romantic places in the world for a destination wedding. The island’s famously spectacular sunsets offer the perfect backdrop for saying “I do”. There’s only one thing that could make it better: holding your reception aboard an equally spectacular Key West yacht rentals. All-inclusive reception cruises are available for wedding parties as large as 300 guests.

Planning Your Wedding Or Event

For such a big and important event, you probably don’t know where to begin, so talk to us. Key West Charter Boat will book your dream yacht, complete with captain, crew and wedding planner. Customize your reception exactly the way you always imagined it, from floral arrangements to food & beverage menus to the perfect song for the bride and groom’s first dance.

Key West yacht rentals can be chartered for as little as an hour or as long as several weeks. Knowing the size and nature of your party will help make the selection process faster and easier, so please take a minute to fill out a quote form. Some of the larger yachts are in constant demand, so the earlier we know your reservation dates the better.

If you have questions, please don’t hesitate to give us a call or use the live chat feature on our website. With years of local knowledge to draw upon, our goal isn’t to simply book you a yacht. It’s to match you with the perfect yacht for your needs and make it unforgettable.

It was our parents 50th anniversary, we wanted to do something special.  Chartering a yacht in Key West was hands down the best choice we could have made.  Our parents loved it and our memories will last a lifetime.

Key West yacht rentals are the very definition of luxury. Whether you’re aboard a 45-foot catamaran cruising Key West harbor or sailing the entire Florida archipelago to Key Largo on a 200-footer, every comfort and amenity is provided. From family vacation Key West Sunset to corporate retreat, there’s a size and design of yacht that’s perfect for your needs.

Call Key West Charter Boat or fill out a quote form. We’ll make all of the arrangements for a boating experience you and your guests won’t soon forget.

If you’re looking for a luxury cat, you’ll find a wide variety to choose from, with hull lengths ranging from 38-feet to over 65. A sailing catamaran’s unique combination of roominess, stability, and speed make it the number one yachting choice in the keys. Cats are available in both sail and power versions with our Florida Keys yacht charters. Both are fully outfitted for luxurious cruising, including air-conditioned salons and berths, multiple heads with showers, and fully-equipped gourmet galleys.

CHARTER QUOTES

Charter Type Charter Type Yacht Charter Deep Sea Fishing Charter Flats Fishing Charter Private Custom Charter Sailing Charter Large Group Charter Overnight Charter Sunset Charter Boat Rental Dry Tortugas Charter Cuba Charter Jet Ski Charter Spearfishing Charter Snorkeling Scuba Diving Glass Bottom Boat Lobstering Charter Dolphin Watching Corporate Boat Party Wedding Charter Film Production Charter Other

A charter cruises with key west yacht rentals

FAST RESPONSE

Charter Type Charter Type Yacht Charter Deep Sea Fishing Charter Private Custom Charter Sailing Charter Flats Fishing Charter Overnight Charter Large Group Charter Sunset Charter Boat Rental Dry Tortugas Charter Cuba Charter Jet Ski Charter Spear Fishing Charter Snorkeling Scuba Diving Glass Bottom Boat Corporate Boat Party Lobstering Charter Dolphin Watching Wedding Charter Film Production Charter Other

Call us

(305) 783-2430

Have questions?  Want immediate answers?  Our expert staff is standing by 24hrs a day 7 days a week to answer all your Key West charter questions.  Call now!

Boat wheel

We chartered a yacht out of Key West to the Dry Tortugas.  The whole experience was absolutely amazing.  Top notch!

     Located so close to the Caribbean, it’s not uncommon for Key West yacht rentals to visit international ports of call. Head southwest and the Yucatan peninsula is a week charter. Due East lie the Bahamas. From there it’s a game of hopscotch, island to island, country to country, down the Caribbean archipelago.  Near or far, if you bareboat, you’ll need to file a sail plan with your charter company, including all ports you plan to visit. Of course, changes can be made en route so long as you keep the company notified.

    Key West is one of the most romantic places in the world for a destination wedding. The island’s famously spectacular sunsets offer the perfect backdrop for saying “I do”. There’s only one thing that could make it better: holding your reception aboard an equally spectacular Key West yacht rentals. All-inclusive reception cruises are available for wedding parties as large as 300 guests.

   For such a big and important event, you probably don’t know where to begin, so talk to us. Key West Charter Boat will book your dream yacht, complete with captain, crew and wedding planner. Customize your reception exactly the way you always imagined it, from floral arrangements to food & beverage menus to the perfect song for the bride and groom’s first dance.

   Key West yacht rentals can be chartered for as little as an hour or as long as several weeks. Knowing the size and nature of your party will help make the selection process faster and easier, so please take a minute to fill out a quote form. Some of the larger yachts are in constant demand, so the earlier we know your reservation dates the better.

   If you have questions, please don’t hesitate to give us a call or use the live chat feature on our website. With years of local knowledge to draw upon, our goal isn’t to simply book you a yacht. It’s to match you with the perfect yacht for your needs and make it unforgettable.

a charter boat sits with Key West Yacht Rentals

Charter Type Charter Type Yacht Charter Deep Sea Fishing Charter Flats Fishing Charter Private Custom Charter Sailing Charter Large Group Charter Overnight Charter Sunset Charter Boat Rental Dry Tortugas Charter Cuba Charter Jet Ski Charter Spear Fishing Charter Snorkeling Scuba Diving Glass Bottom Boat Dolphin Watching Lobstering Charter Corporate Boat Party Wedding Charter Film Production Charter Other

a boat on charter cruises with Key West Yacht Rentals

Key West Yacht Rentals – Motoring Charter

Girls drinking champagne with key west yacht rentals

Key West Yacht Rentals – Champagne Party

A charter sails with Key West Yacht Rentals

Key West Yacht Rentals – Sailing Charters

a family relax's with Key West Yachts

Key West Yacht Rentals – Family Time

a couple vacations on a catamaran charter with Key West Yachts

Key West Yacht Rentals – Couples Vacation

Friends have fun with watersports with Key West Yacht rentals

Key West Yacht Rentals – Watersports Fun

Pool party on a boat charter with Key West Yacht Rentals

Key West Yacht Rentals – Pool Party

Customers enjoy their jacuzzi on a key west yacht rentals charter

Key West Yacht Rentals – Jacuzzi Cruise

Best Charters Best Prices

A marlin jumps during Key West Yachts offshore fishing trip

Custom Fishing

Custom Fishing Trips…

Key West Yachts Overnight Charters sleeping quarters

A Deliciously Fun Time…

A Yacht Cruises During a Key West Yachts Charter.

Luxury Yachts

The Best Or Nothing…

Man hunting for Mahi Mahi with Key West Yachts

Key West Charter Boat,

3200 Harriet Ave,

Key West, FL 33040

United States Of America

Yachting in Key West, FL

Yachting in Key West, FL

Located at Florida's southern tip, Key West captivates with azure seas, vibrant coral reefs, and a relaxed vibe. Experience the island's allure and enjoy luxury yachting in Key West, FL. Perfect for leisurely cruises or thrilling adventures, Key West is ideal for sun-filled coastal experiences. Discover its beauty from the deck of your private yacht.

52 Viking Princess luxury charter yacht - Galleon Marina, 619 Front St, Key West, FL 33040, USA

52' Viking Princess

80 FF Pendleton luxury charter yacht - Key West, FL, USA

80' FF Pendleton

75 Multihull luxury charter yacht - Key West, FL, USA

75' Luxe Catamaran

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Once you confirm your reservation, your broker will process your payment.

  • If you are booking for a single day and your reservation is confirmed more than 7 days in advance, a deposit of either $1,000 USD or 50% of the total cost of the reservation (whichever is greater) is processed immediately in order to hold the yacht. Once your embarkation date is 7 days away, the remainder of the amount due is processed.
  • If you are booking for a single day and your reservation is made 7 days or less in advance, the total price of your reservation is processed immediately.
  • If you are booking for a multi-day charter and your reservation is confirmed more than 30 days in advance, a deposit of 50% of the cost of the yacht is processed immediately in order to hold the yacht. Once your embarkation date is 30 days away, the other 50% is collected for the price of the yacht, plus the APA, plus the taxes due.

Terms of refunds are dictated by the Charter Agreement. Generally, once a payment is collected, it is non-refundable. In certain circumstances, as dictated by the Charter Agreement, credits can be provided so you will be able to enjoy your yacht charter at a future date that is convenient for you.

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Key West Yacht Rental

Welcome to Anchor Yacht and Boat Rentals, your premier destination for the ultimate Key West boating experience. Nestled in the heart of Key West, Florida, our fleet of luxurious yachts and boats awaits, ready to provide you with an unforgettable adventure on the crystal-clear waters of the Gulf of Mexico and the Atlantic Ocean.

At Anchor Yacht and Boat Rentals, we take pride in offering a diverse selection of vessels to suit every taste and occasion. Whether you're seeking a romantic sunset cruise, a thrilling deep-sea fishing expedition, or a relaxing day of snorkeling and swimming, our boats and yachts are equipped to make your dream day on the water a reality. Our team of experienced captains and crew members are dedicated to ensuring your safety and enjoyment throughout your journey.

Our Key West boat and yacht rentals are not just about transportation; they're about creating memories that will last a lifetime. Picture yourself sipping champagne on the deck of one of our elegant yachts as the sun dips below the horizon, casting a golden glow on the sea. Imagine the thrill of reeling in a trophy fish or the wonder of exploring vibrant coral reefs teeming with marine life. These are the experiences that await you when you choose Anchor Yacht and Boat Rentals.

Whether you're a seasoned sailor or a first-time boater, our team is here to make your adventure exceptional. So, why wait? Contact us today to book your Key West boat or yacht rental and embark on an unforgettable journey with Anchor Yacht and Boat Rentals. Your dream day on the water is just a click or a call away.

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Catamaran Charter Key West - Catamaran Rentals

Top-rated yacht charters in key west - preselected yacht rentals:.

Cat Leopard 40 available for charter in Key West

Cat Leopard 40 available for charter in Key West

  • Leopard 40 [Yacht Price incl. Taxes]
  • Outboard engine for dinghy
  • Yacht Insurance
  • Final cleaning
  • VAT or sales tax

Catamaran Lagoon 46 for rent in Key West

Catamaran Lagoon 46 for rent in Key West

  • Lagoon 46 [Yacht Price incl. Taxes]
  • Skipper (food not included)

Catamaran Bali 4.2 available for charter in Key West

Catamaran Bali 4.2 available for charter in Key West

  • Bali 4.2 [Yacht Price incl. Taxes]

Catamaran Summerland 40 for rent in Key West

Catamaran Summerland 40 for rent in Key West

  • Summerland 40 [Yacht Price incl. Taxes]
  • Cockpit cushion

Cat Bali 4.1 available for charter in Key West

Cat Bali 4.1 available for charter in Key West

  • Bali 4.1 [Yacht Price incl. Taxes]
  • Fishing equipment
  • Snorkeling equipment
  • Cook (food not included)
  • Beach towel
  • Stand up paddle board

Catamaran Lagoon 42 for hire in Key West

Catamaran Lagoon 42 for hire in Key West

  • Lagoon 42 [Yacht Price incl. Taxes]
  • Barbeque Grill
  • Charter tax
  • Charter certificate
  • Cruising tax
  • Administration fee
  • Fuel (for dinghy engine)
  • Charter package (Final cleaning, Bed linen, Towels, Kitchen gas, Dinghy with engine, Starter package, Damage Waiver)

Catamaran Saona 47 for rent in Key West

Catamaran Saona 47 for rent in Key West

  • Saona 47 [Yacht Price incl. Taxes]
  • Barbeque Grill (gas)

Cat Lucia 40 for rent in Key West

Cat Lucia 40 for rent in Key West

  • Lucia 40 [Yacht Price incl. Taxes]
  • Rubber Dinghy

Catamaran Lagoon 450 for rent in Key West

Catamaran Lagoon 450 for rent in Key West

  • Lagoon 450 [Yacht Price incl. Taxes]

YACHTICO.com brand logo

Catamaran Leopard 50 PC for hire in Key West

  • Leopard 50 PC [Yacht Price incl. Taxes]

YACHTICO.com brand logo

Catamaran Saba 50 available for charter in Key West

  • Saba 50 [Yacht Price incl. Taxes]
  • Dinghy with engine
  • Full board (Food + Drinks / 3 meals)

Crewed Luxury 75 Ft Catamaran in Key West

Crewed Luxury 75 Ft Catamaran in Key West

  • Custom [Yacht Price incl. Taxes]

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  • Rental Property #16214

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Paradise #1

About this rental

  • Bedrooms: 1
  • Bathrooms: 1
  • Property Type: Yacht
  • Minimum Stay: 2 nights
  • Living Area: 2000 sq. ft.

We specialize in amazing vacations and honeymoon and extended stays for two guests, aboard a yacht that stays dockside without the chance of seasickness allowing you to come and go according to your own schedule. Our pedigree Hatteras, a custom 60' motor yacht, a timeless classic designed for elegant entertaining docked in a safe harbor offering parking, central air, large kitchen, panoramic waterfront views of mega yachts, shrimp boats and sail boats. The ships bow boast one of the most beautiful in Key West with plenty local charm. With a large comfortable salon that connects to the "Whale's Tale" bar to enjoy your favorite drink and tell your special stories. Aft of the bar our double teak door open to the fishing deck, complete with a swim deck for those who want to take a quick dip in our sparkling water. The bar also leads to the top deck, it is very private and overlooks the entire bay and ideal for chilled champange and a good book. This ship is a perfect retreat where you can find some private time to spend with the one you love. Whatever you desire your crew will make your time onboard perfect. The beautiful luxury yachts sleeps two in a stateroom with queen bed, en-suite head and shower, wi-fi and steaming television with movie stations, offers maximum privacy and comfort. Our highly professional crew will make you time onboard perfect. Yacht Paradise crew with a well behaved Dorkie named Willow Meena. Crew are completely separeted with an outdoor entrance to their cabin. They keep the ships systems operating smoothly and keep common areas clean and provide passenger safety. Highly trained in hospitality services. Early check in/late check out, subject to availability. Complimentary wi-fi and pick up and drop off at Key West airport or Free Parking if making the magical drive down the overseas highway.

Unique Benefits

Free Parking Free Wi-fi Onboard Cash Honor Bar Use of full kitchen Two spacious outdoor decks that allow smoking (outside only) Complimentary Airport Pickup and Drop Off

Area Information

Top Covered Deck with Dining Bar Main Salon with large TV Central A/C Queen size suite with enclosed head and shower Full Kitchen Bow deck with Table for Dining Back Lounge Deck

Attractions Within Walking Distance

2 five star resestaurents on premeisis

Favorite Places To Eat

Hogfish Bar and Grill steps from the Dock The Docks Restaurant and Raw Bar Salute on the Beach Only Wood Bagatelle

  • 1 Queen Bed
  • Air conditioning
  • Beach chairs
  • Bed linens provided
  • Daily maid service
  • Dock or boat slip
  • EV car charger
  • Kid friendly
  • Managed by owner
  • Parking available
  • Patio or deck
  • Pets allowed
  • Smoking allowed
  • Towels provided
  • Wireless internet
  • Carbon monoxide detector
  • Coffee maker
  • Dishes & utensils
  • Refrigerator
  • Smoke detector
  • Aquarium (onsite)
  • Beach (1 mile)
  • Bicycling (
  • Boating (onsite)
  • Deep Sea Fishing (
  • Grocery Store (2 miles)
  • Gym/Fitness Center (
  • Jet Skiing (
  • Live Entertainment (onsite)
  • Movie Theater (2 miles)
  • Ocean (onsite)
  • Parasailing (
  • Sailing (onsite)
  • Scuba Diving (
  • Shopping Area (2 miles)
  • Snorkeling (onsite)

Other Vacation Rental Amenities

30' Catermeran with Captain to play in the waters of Key West, snorkel, Dolphin watch, Sunset, Additional Charge

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Fantasy Week and Christmas week nighty rate $450.00

Last updated on April 08, 2024

Hosted by Chris Doherty

Chris Doherty

Member since 2023

Year Purchased: 2023

About the owner: My wife and I purchased this Yacht from the previous owners that worked in the charter boat industry for over 40 years. We love Key West and since we have been together wanted to purchase a Bed and Breakfast on the island. The dream was slipping out of reach, due to pricing of property in Key West became prohibitive, when the opportunity of Yacht Paradise fell into our lap. It took the stars aligning and the perfect timing. Here we are to give you and your group the beast experience of Key West Possible. We fell in love with the Classic 60' Hatteras that has become our Boatel (boat/hotel). In the perfect location in the historic fishing enclave of Stock Island there is a feel of how Key West was 50 years ago. Yet still close to the action of Duval Street, the fabulous cuisine, and amazing culture only found in this place, Welcome to Paradise

Why this property? Fun, comfortable, close to all Key West activities. Unique lifetime memories. This is a one of a kind stay on a floating hotel. The gentle movement of the harbor will lull you to sleep. Watch amazing sunsets over the bow as we face due West. Truly a one of a kind experience!

Paradise #1

Great experience!

The Paradise is a grogerous yacht. The woodworking is amazingly beautiful. The bed is very comfortable. We really enjoyed our stay and was very pleased. Captain Berry & Tamara were very tentative and superior host. I would stay again and highly recommend the Paradise yacht.

Stayed: January 2024 Submitted: January 06, 2024

Enjoyed our stay onboard "Paradise" M/Y in Key West. Beautiful yacht with excellent accommodations and plenty of room to roam about. Two popular restaurants just a few steps away from the yacht. Key West is a short ride away. Enjoy strolling Duval and partake in the local flavor, whether that be food or drinks. Nightlife is the best of blues and views. Finish your evening off with a nightcap aboard "Paradise". Kickback, relax and enjoy your view. Thank you Captain Barry and Tamara for making our stay a great time. Warning: we will be back.

Stayed: April 2023 Submitted: April 22, 2023

Owner response

Thanks for the great review, we both had a good time with you both, come back soon.

Chris Doherty

Contact Host

About the property

vacation yacht rentals key west

Phone: (305) 587-3499 Email: [email protected]

Fun In The Sun Key West, FL.

  • Rental Boats
  • Stay & Play Package
  • Sandbar Charters
  • Boat Bar Crawl
  • Fishing Charters
  • Ft. Jefferson & Dry Tortugas
  • Key West Yacht Charters
  • Captained Combo Charters 1-6 People
  • Bareboat Charter 7-12 People
  • Charter Activities
  • Shared Key West Charters
  • Cancellation Policy
  • Golf Cart Rentals
  • Bike Rentals
  • Paddle Board & Kayak
  • Jetski Tours
  • Vacation Rentals

Fun In The Sun Key west Boat Rentals & Charters

Come enjoy the original Key West sandbar charter !  We specialize in custom private charters and boat rentals . Keep the fun going with the best golf cart , bike, kayak & paddle board tours and rentals Key West has to offer. Now booking Day Trips to The Dry Tortugas & Fort Jefferson.

We provide high-quality private charter and boat rental excursions of the beautiful Key West area. Experience areas off the beaten path, and have a boat all to yourself. Some of the trips offered are snorkeling, relaxing sandbar trips, fishing, dolphin watching, lobstering, party booze cruises, and whatever else the guests can come up with! Don’t compromise customer service, freedom to do activities at your own pace, and comfort, by being packed on larger vessels with other people. You will feel like you are on a friend’s boat when you are our guest. High-quality equipment, caring staff, attention to detail, safety, and customer satisfaction are at the top of our priorities. See more about our Boat Charters and Activities here. If you are looking to experience the island on wheels, our Key West Golf Cart Rentals will get you where you want to be. Please call or text 305-587-3499 for reservations and questions. Rated 5 stars on TRIPADVISOR . For charter information, navigate to our CHARTER DETAILS page, for boat rentals navigate to our BOAT RENTALS  page, for golf carts navigate to our  GOLF CART RENTALS page or Book Online below.

Fun In The Sun Key West Watersports @ The Capitana Resort offers Paddle Board & Kayak Rentals & Tours for a relaxing day exploring the mangroves and grass flats. Come check out the backcountry with hourly rentals or guided tours. For an easy way to get around the island, our Capitana location also offers Key West Bike Rentals .

Home of the original “Key West Sandbar Charter”

A Key West Sandbar Charter is the perfect way to experience the backcountry paradise of our sandbars. Fun for the entire family, our Key West sandbar trips give you the best experience in Key West, letting you see the natural treasures and beautiful surroundings with your own private charter. We can help you make things even more memorable with a custom itinerary, and we are happy to arrange a special day to suit your group whatever they are looking for. Fully licensed and insured, we have extensive experience in providing the exceptional sandbar experience you are looking for. With some of the best sandbars in the world, it really is an unforgettable location and no trip to Key West is complete without a Key West sandbar charter.

See more details about the original Key West Sandbar Charter here.

We have a range of tours and options to choose from, whatever your style, whatever your group, Fun In The Sun Charters are here to make this the best trip possible.

CHARTER ACTIVITIES:

-dolphin watches -sandbar trips -sunset booze cruises – snorkeling, -backcountry exploring -island hopping -fishing -birdwatching, -lobstering during season -sunset cruise -around key west sightseeing tour.

vacation yacht rentals key west

Trip-Combinations are possible and encouraged, give us a call and we will customize a trip for you! Call or text (305) 587-3499

Fun In The Sun Charters & Boat Rentals offers a great selection of various way to experience being on the water in Key West, FL.

View Our Locations:

Please refer to the charter or rental booking confirmation for the location of departure.

ALL CAPTAINED CHARTER BOATS

Stock Island Yacht Club 6000 Peninsular Ave, Key West, FL 33040 Get Directions

PADDLE BOARDS, KAYAKS & BIKE RENTALS

The Capitana Key West 2401 N Roosevelt Blvd, Key West, FL 33040 Get Directions

RENTAL BOATS (CALL TO CONFIRM LOCATION)

Blue Ocean Yacht Charters

Overnight Boat Rental Key West

by "Charter Booker" | Dec 23, 2017 | Overnight Yacht Vacation Rentals

Key West yacht

Overnight boat rental in Key West, Florida is a popular option.  Many people like to take in a sunset sail or a full day excursion, snorkeling, swimming, relaxing and sailing.  There’s so many reasons why you’ll love an overnight boat rental in Key West, Florida, as alternative accommodation, but here’s 5 of our favorites:

Guaranteed water views!

Forget a room with a view…stay in the view, on a yacht in Key West, Florida! You’re at water level on a yacht in Key West. See fish and other marine wildlife swim right up to your yacht. Manatees are common marine wildlife you can see while staying overnight on a yacht in Key West, Florida.  From time to time it is not uncommon to see a dolphin or two swim by on a boat in Key West, Florida.

Wow factor on an overnight boat rental

Get a slice of laid back luxury in your life on a yacht in Key West, Florida.  It’s common to stay at a hotel or in a house, but how common is it to stay overnight on a vacation rental that floats in Key West?  Book your next vacation rental on a yacht today in Key West. Stay overnight, take a sunset sail, or enjoy a full day excursion out on the water while being in your home on a boat in Key West, Florida.

Family friendly overnight boat rental 

Kids can have their own cabin. Most of our yachts in Key West will sleep a couple families making this amazing stay on a yacht in Key West an incredible vacation. They can jump on many of our yacht’s trampolines, fish, and for those daring, can even jump off the yacht in Key West into the ocean blue water.  Overnight on a yacht in Key West is a vacation rental dream come true.

Quality time

Swap the screens for open skies & stars. There’s nothing better than laying on the deck of your favorite boat in Key West, under the stars, unplugged, and taking all that Mother Nature has to offer staying on a boat in Key West, Florida.

Save money with an overnight boat rental 

All this for less than a hotel room in Key West, Florida. Many hotels in Key West, Florida are over-priced due to the fact that Key West, Florida draws overnight vacation rentals from all over the world.  Vacation rental customers do not know how inexpensive it is to stay on a yacht in Key West Florida.  Whether you are looking to rent a boat in Key West, Florida, the cost savings can be huge. https://blueoceanyachtcharters.com/contact/

Happy Sailing,

“Charter Booker!”

(Charter Booker, manages Blue Ocean Yacht Charters in Key West and writes many of the company’s blogs.  He has experience both on the water and off the water helping customers experience the best possible yacht charter.  Carrying American Sailing Association certifications with extensive knowledge of boat safety and regulations makes him the charter authority.  Call 305-923-4152 and ask for “Charter Booker” when booking your next yacht charter in Key West, Florida.)

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sunset over a pool at a VRBO in key west florida

13 Best VRBO Vacation Rentals In Key West (Cottages, Yachts, & More!)

April 18, 2021 //  by  Florida Trippers

The perfect VRBO in Key West is waiting for you! Get ready to explore several different styles and locations. We can’t wait for you to see all of the stunning views, fabulous pools, and amazing amenities.

Key West is a fabulous place to visit because it is filled with entertainment, beachside beauty, and friendly hospitality. After a long day of fun in the sun, you will want somewhere comfortable to rest your head. Staying at any one of these vacation rentals will be a missing piece to your ultimate trip!

In addition to amazing beaches and a perfect laid-back vibe, Key West has some of the most incredible Key Lime Pie you will ever taste. Check out the 7 Best Places To Get Key Lime Pie In Key West ! Do you love breakfast food? Then, you’ll definitely want to explore the 14 Best Places For Breakfast In Key West.

So, why should you stay at a VRBO in Key West? Well, for starters, you get a more home-like feel! Secondly, you tend to get more privacy. Lastly, you can find some really unique and fun properties!

Vacation rentals offer a wide range of prices, so whether you want a super luxe experience or want to stick to a budget, you can find it all here. Keep reading and we will help you find your ideal match!

The Boardwalk to a beach in Key West

13 Best VRBO Vacation Rentals In Key West (Cottages, Beach houses, & More!)

We can absolutely see why this VRBO in Key West is named Songbird! You will be as happy as a bird singing in Spring when you see this beautiful retreat. Songbird is a stunning home with 3 bedrooms and 2.5 baths.

The first thing that jumped out at us was the gorgeous pool! The pool and lounge area are very lush and peaceful. The second highlight is the phenomenal décor and styling throughout the home. It is fresh, bright, and welcoming! This is truly one of the Best Places To Stay In Key West!

Guests will love the soaking tub, French doors, and cozy living room. Up to 6 guests can be comfortably accommodated at the moderately priced “Songbird” house.

>>>Check Rates: VRBO.com

Photo of the exterior of a cottage-style home with pool that is a VRBO in Key West.

Mango Margarita

Next, we visit a luxury 2/2 that is located in Old Town. Mango Margarita is striking from the start! A bright orange front door greets you as you enter your very own tropical oasis! Fun pops of color continue throughout this VRBO in Key West.

In addition to being incredibly cute, this home is just one block from the very popular Duvall Street! Mango Margarita has 2 King size beds and a sleeper sofa, so up to 6 guests can enjoy a comfortable stay. This is truly one of the Best Places To Stay in The Florida Keys!

Mango Margarita includes a full kitchen, a living room, a formal dining table, and a pool with covered seating. We really love that you get to enjoy pool views from the living room.

Photo of a vacation rental featuring a pool with covered lounge area.

Luxury Yacht

Now, we get to share a truly unique vacation rental with you! Staying on this Luxury Yacht is the ultimate in tropical seclusion. Up to 6 guests can be accommodated aboard this stunning 3 bedroom and 2 bath yacht.

One of the special features of this VRBO in Key West is the bow access from the covered upstairs flybridge area. Guests will love being able to hang out upstairs for evening cocktails, morning breakfast, or sunbathing.

The yacht remains docked in a beautiful marina throughout your stay. Additional entertainment can be purchased including sunset cruises, fishing charters, and more!

Photo of a 3/2 luxury yacht that is white with a blue canopy over the upstairs flybridge.

Charming 1 Bedroom Apartment

Are you looking for elegance and affordability? Well, look no further than this Charming 1 Bedroom Apartment ! The apartment is located right on White Street and features wood floors, high ceilings, and a full gourmet kitchen.

The color palette consists of crisp white walls, stylish blue velvet lounge chairs, and warm blonde wood. The bedroom features a very romantic and chic crystal chandelier.

In addition to its wonderful interior, there is a lovely fenced-in backyard. Staying at this VRBO in Key West will conveniently place you within walking distance of a grocery store, sandwich shop, and fabulous Cuban coffee.

Photo of a living room and kitchen inside a VRBO in Key West. It features wood floors and blue velvet lounge chairs.

Key West Oasis

Now, we visit a really unique and special VRBO in Key West. The Key West Oasis is a 2 bedroom house, but the second bedroom is in a separate cottage. If you are traveling with another couple, this would be the ideal arrangement for privacy.

The entire home has been completely renovated to create a resort-style environment. The pool and lanai area are completely private with lush landscaping.

The Key West Oasis is a luxury stay located right in Old Town. You will be conveniently close to Duvall Street, restaurants, and bike rentals.

Photo of a pool and lounge area with lush garden surrounding and a cottage.

Serendipity

When we picture the quintessential Key West home, Serendipity is exactly what comes to mind! Serendipity is a grand 4 bedroom and 4.5 bath home that is incredibly dreamy!

Where do we begin? Well, for starters, the first impression as you approach this home is outstanding! You are met with a pristine white fence and a gorgeous two-story home with a wooden door just beyond it. Additionally, bold shutters and the upper balcony really stand out.

Secondly, you will be dazzled by the Brazilian cherry floors, Dade County Pine walls, and high ceilings that all come together to create a stunning aesthetic. Third of all, several sets of French doors allow you to open the home and enjoy a real island experience.

Other special highlights include a large pool with lounge area, indoor and outdoor dining, claw-foot tubs, and luxury bathrooms! Serendipity can accommodate up to 8 guests and allows cats and dogs(under 30lbs).

Photo of the front exterior of a beautiful 2-story VRBO in Key West.

Octagon House

The Octagon House was formerly owned by Calvin Klein and is currently an iconic signature home in Key West. The decor is sophisticated with a subtle tropical flare. Staying at this luxury home will provide you with a relaxing and calming environment.

Highlights include a poolside entertainment lounge area, resort-style baths, and an integrated sound system. Up to 8 guests can be accommodated with 4 bedrooms and 4 baths. Octagon House is definitely a huge splurge, but it has style, location, size, and luxury!

Some other amenities include an outdoor shower, a ping-pong table, and a gourmet kitchen. The Octagon House is centrally located, so you can easily walk or bike to any destination.

Photo of the front exterior of the "Octagon House" that is white with aqua shutters.

Petunia Cottage

Petunia Cottage is a super cute, cozy, and affordable VRBO in Key West. The cottage has been fully renovated, it is located in Old Town, and it can accommodate up to 4 guests.

If you want to be close to all of the most popular tourist attractions and historic homes, then this is the spot for you! Staying at the Petunia Cottage places you within walking distance of several shops, restaurants, and art galleries.

The cottage is appointed with beautiful artwork throughout. A covered patio is located just off the kitchen and would be perfect for evening cocktails.

Photo of a white cottage in Florida with a white picket fence and wooden doors.

Caroline On My Mind

Caroline On My Mind is a wonderful 2 bedroom condo that features a private balcony overlooking Caroline Street. The second-floor condo is conveniently located just 2 blocks from Duvall Street.

Up to 4 guests can be accommodated at this affordable VRBO in Key West. We really love how the second bedroom is reached by a spiral staircase.

The condo includes a common area featuring a heated pool. Other highlights include antique glass windows, hardwood floors, marble counters, and designer furniture.

Photo of a living room featuring a spiral staircase inside a VRBO in Key West.

Dog-Friendly Home With Private Pool

Do you want to visit Key West and bring your dog with you? If so, this Dog-Friendly Home With Private Pool might be exactly what you need!

Conveniently located in Central Key West, staying at this home will place you in a prime location for exploring shops, restaurants, beaches, historic landmarks, and dog parks!

Enjoy your day sightseeing, then come back to relax on the porch or by the pool. The home is moderately priced and can accommodate up to 3 guests with 2 bedrooms, 2 beds, and 1 bath.

Photo of a yellow home with a private pool and lounge area.

Casa De Cuba Beach House

Now, let’s check out Casa De Cuba Beach House , which features a fabulous location, Cuban flair, and 21 foot-long pool. The beach house is definitely a luxe VRBO in Key West with tons of character and ambiance.

Casa De Cuba is just half a block from Duvall Street, so you will be in a prime location for all things Key West! It is worth noting that one of the best homemade ice cream parlors is just down the street. Just picture taking a short stroll for a cooling afternoon treat!

The beach house has 3 bedrooms and 2 baths, therefore, it can accommodate up to 6 guests! Some of the standout amenities include the front porch swing, pool with lounge area and covered seating, and the handcrafted spacious dining table.

Photo of the 21 foot-long pool at Casa De Cuba VRBO in Key West.

Oceanfront Paradise

The Oceanfront Paradise is a 2-story home with 5 bedrooms and 4 baths that features a breathtaking pool with a waterfall! Now, let us tell you, this pool is epic!! The pool not only has a spa and waterfall, but it also has one of the most stunning ocean views ever.

Up to 12 guests can enjoy this fabulous VRBO in Key West! There is a private entrance on each level for ultimate privacy. Guests will love exploring the waterfront with the included ocean kayaks!

Oceanfront Paradise is a complete luxury property with lush landscaping including banana, mango, and starfruit trees. Neighborhood amenities include mini golf, tennis courts, basketball courts, playgrounds, sand volleyball, and more!

Photo of an oceanfront pool with a spa and waterfall that is located in Key West.

Casa Cayo Hueso

Casa Cayo Hueso is located in Old Town and is set at a very affordable price point. The 3/2 house has classic Shotgun architecture and Dade County pine wood floors.

The large and spacious kitchen that is fully equipped will make preparing meals super easy. The backyard deck is perfect for relaxing, grilling, and enjoying meals because it features covered seating and a dining table.

Special amenities include an outdoor shower, private Jacuzzi, and private parking. Watersports entertainment, restaurants, and shops are all within walking distance.

vacation yacht rentals key west

Well, hope you have enjoyed touring our selections and you find your dream VRBO in Key West! We wish you a wonderful vacation filled with sunshine, adventure, and special memories.

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LOVED our stay!!

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Bungalow in Key Colony Beach

Coral Quay-III Canal waterfront,access BEACH club!

3- minutes from boat launch!!! 60 feet of boat dockage!!! by home-plenty of parking for Vehicle and trailers. Bait freezer on dock next to fish table. Quick to ocean( 5-min.) Gulf (15 min.)from dock. We are pet friendly. Home is a large 3-bedroom that ALSO has two queen sofa sleeper. WiFi with HD-TV. Access to private Ocean Beach Cabana Club. The club has a spa/whirlpool,bar,grill, pool overlooking ocean and a beach. The club is a 5-minute walk away. "Key Colony Beach" Called "Gem"of the Keys

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Bungalow in Islamorada

Beautiful Bay and Beach Bungalow

We are a great location for stays of 28 nights or more. Contact owner with any questions. WiFi Internet connectivity is provided. Unassuming and relaxed elegance. Swim right off the dock or off Sea Oats Beach just out the front gate. Great deep dockage and quick access to bay and ocean!!! Spectacular long water views from inside and out of this secluded property! The dockage is deep and can accommodate large deep draft boats. Electric, water and light are conveniently located at the dock.

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Bungalow in Key Largo

Cozy Bungalow w/ Sunset Ocean View at Largo Resort

Bungalow Row at Largo Resort is comprised of six luxurious suites. Our one Bedroom Sunset Bungalow offers an amazing ocean view and is directly across our water front pool. Offering 1 private room entrance with a King Size Bed and Private Bathroom and Private entrance to the Queen Size Bed Room that offers a Mini Fridge, Nespresso, Microwave, Living room and private bathroom. The full time caretaker, housekeeper, and concierge service is dedicated to make your visit a life time experience!

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Bungalow in Cudjoe Key

Island Therapy

Check out my other property right next door! Beautiful 2BD/2BA vacation home features open water views and a full size 35' seawall for docking a boat. Beautiful open water views and quick access to the ocean or gulf from this property. 7 day minimum during lobster season. No Smoking, No Pets. There is a resort usage fee of $125 payable upon arrival at Venture Out. Pre-registration form of guests must be completed prior to stay or when checking in at the security gate.

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Islamorada Bungalow 2 Bed/1 Bath & Pool Unit 4

Escape to our charming 2-bedroom, 1-bathroom bungalow in Marathon, FL, where luxury and convenience await! Relax on the spacious patio and take a refreshing dip in the pool, perfect for unwinding after a day of exploring nearby attractions. You're just moments away from pristine beaches, world-class fishing spots, and a variety of dining options. Whether you seek adventure or relaxation, our bungalow offers it all. Secure your stay now for an unforgettable experience!

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Islamorada Bungalow 2 Bed/1 Bath & Pool Unit 3

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Islamorada Bungalow 2 Bed/1 Bath & Pool Unit 5

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Bungalow in Key West

Atlantis House's Banyan Suite-voted top 25 in USA

This suite The Banyan Suite (previously called Garden Suite) is nestled in the corner of the lush backyard with a private French door entrance off the deck. This charming hideaway offers a large flat screen TV visible from the sofa and spacious king bed. RA corner bar table provides the perfect spot to enjoy a quick bite from the quaint kitchenette equipped with a mini-fridge, microwave oven, toaster, and coffeemaker, featuring famous Cuban coffee!

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Dream in Paradise! King Master, Queen Guest, Pool

Castaway Island! Luxury In paradise! This hidden gem is your piece of paradise waiting! Fully remodeled and furnished from the floor up. All new furniture, fixtures and furnishings await. One of the most well appointed and private Bungalows in Islamorada. Perfect for the honeymooners and special occasion couples and small families. Private outside spaces. 4 Bikes, 2 ultra lite SUP's, 2 Kayaks, 4+ beach chairs, ice chests and more await you.

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Atlantis House's Palm Suite-voted top 25 in USA

The luxurious 650 square foot Palm Suite (previously known as Master Suite) overlooks the lush backyard from the private French door entrance. Once inside, 17-foot vaulted ceilings accentuate the large flat screen TV visible from the stylish sofa and comfy king bed. RPrepare a quick bite at the breakfast bar equipped with a mini-fridge, microwave oven, toaster, sink, plates, utensils, Mueller coffeemaker and famous Cuban coffee!

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Cudjoe Key OCEANFRONT 2B/2B in gated community!!

Check out my other property right next door! Sparkling clean and beautifully remodeled 2Bd/2Ba vacation home that features OPEN WATER views with great boating access to the ocean or gulf! This waterfront paradise features a 35' concrete seawall. There is a resort usage fee of $125 payable upon arrival to Venture Out. Pre-registration form of guests must be completed prior to stay or when checking in at the security gate.

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Lovely Bungalow w/ Plenty Of Shade At Largo Resort

Bungalow Row at Largo Resort is comprised of six luxurious suites. Our Twilight / Sunrise Bungalow is a 1 Bedroom Bungalow that sleeps 4. It offers a King Size Bed with Private Bathroom and in the living room area a queen size bed with a Mini Fridge, Nespresso, Microwave, and Private Bathroom. The full time caretaker, housekeeper, and concierge service is dedicated to make your visit a life time experience!

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Where to Stay Near Glacier National Park

By Emily Pennington

best small towns in america Whitefish Montana

All products featured on Condé Nast Traveler are independently selected by our editors. However, when you buy something through our retail links, we may earn an affiliate commission.

There’s something truly spectacular about the Northern Rockies, and more specifically, Glacier National Park. From its striated, sky-high peaks to its thundering waterfalls and alpine meadows brimming with wildflowers, there’s a little something for everyone at this Montana haven. Wildlife seekers will enjoy the chance to witness grizzly bears and moose in their natural habitat, and hikers will appreciate the opportunity to lace up their boots and tackle the park’s hundreds of miles of trails .

Of course, it’s no secret that Glacier is home to show-stopping beauty. In fact, it’s such a popular area that the National Park Service reinstated its vehicle entry reservations for this summer. As such, it’s more important than ever to book your lodging early, whether you’re staying at a historic lodge, cozy log cabin , or fabulous glampsite. Read on for our favorite places to stay in and around Glacier National Park.

Interested in sleeping under the stars? We’ve got you covered there, too.

Discover the best places to stay:

The best rentals, the best hotels, the best dude ranches.

This article has been updated with new information since its original publish date.

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Bed and bath: 3 bedrooms, 2 baths Top amenities: Riverfront views, fireplace, outdoor deck with a grill Best for:  Staying close to the park

River Haus is as close as you can get to the gates of Glacier without sleeping inside the park proper. As such, it’s great for adventurous travelers who like to get up and explore—without the requisite long car ride. Wake up and sip coffee in the home’s private yard, taking in the phenomenal views of the Middle Fork of the Flathead River, or snuggle up by the wood-burning fireplace. Then, after exploring Going-to-the-Sun Road by car or bicycle, enjoy dinner in the midcentury-style dining room, or grill out back with a glass of wine in hand.

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Historic homestead with hot tub views

Bed & bath:  2 bedrooms, 1 bath Top amenities:  Hot tub, mountain views, playground, firepit Best for:  Families seeking quiet solitude

Not only is this updated, century-old homestead a photographer’s dream, it’s surrounded by sweeping, panoramic mountain views and boasts a deck-level hot tub for late-night stargazing . Inside, you’ll find bold but tasteful western decor (think black and white stills of whitetail deer and loads of reclaimed wood), as well as room for the whole family, all a mere 15 minutes from the national park.

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Kim’s Trading Post Cabin

Bed and bath: 1 bedroom, 1 bath Top amenities: Kitchenette, grill, hot tub Best for:  A unique Wild West experience

Tucked away in a cabin rental community that’s fashioned to look like a Wild West town of yesteryear, Kim’s Trading Post is an adorable getaway for those who want the old-school Montana experience—without sacrificing creature comforts. A good-sized kitchen, dining nook, and a lounge area with a flat-screen TV greet you when you first walk in, though the focal point is surely the space’s plush, king-size bed. Dates taken? Check out the host’s other Fort Williamson tiny homes for rent.

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Creekside Crossing House

Bed and bath: 3 bedrooms, 3 baths Top amenities: Firepit, indoor and outdoor games, dedicated workspace, chef’s kitchen Best for:  Gathering the whole family together

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Ideal for families or large groups, this three-bedroom Coram home sleeps six (one king, one queen, and one bunk bed) and is brimming with thoughtful amenities. Roast s’mores outside over the large firepit, snuggle up for a movie night on the plush couch, or settle in and play one of the home’s board games when the weather turns sour. After a scenic in-park drive or a hike to stunning Avalanche Lake (the rental is a mere nine minutes to the park’s western edge), fry up a feast in the lavish full kitchen and enjoy supper in the dining room.

Where to Stay Near Glacier National Park The Best Hotels Dude Ranches and Glamping Sites

Luxe 1906 Barn

Bed & bath:  2 bedrooms, 3 baths Top amenities:  Phenomenal deck views, full kitchen, washer and dryer Best for:  Families staying on the east side

Rustic wood walls and a shingled exterior pair perfectly with plush bedding and warm-toned rugs at this real-deal barn turned vacation rental in the Blackfeet Reservation on the eastern edge of Glacier. With ample space to spread out and unwind after hiking to brilliantly blue alpine lakes, this two-story home can comfortably sleep up to eight. Sip your morning coffee while enjoying panoramic mountain views from the upper deck or enjoy a relaxing bath before bedtime. Either way, you’ll be a stone’s throw from top sights like Two Medicine Lake and Going to the Sun Road.

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Quintessential Whitefish cabin

Bed & bath:  1 bedroom, 1 bath Top amenities:  Outdoor dining nook, eat-in kitchen, flat screen TV, woodburning stove Best for:  Serenity and views, just outside of Whitefish

Named the friendliest city by Expedia users in 2021, Whitefish is the perfect base camp for outdoorsy travelers looking to explore Glacier National Park, and this quaint wooden cabin will make you feel instantly at ease. Little details are what makes this place so homey, like bird houses, colorful bursts of wildflowers, a private three-acre lake, bistro seating on the private patio, and warm-toned geometric rugs. Retire to your very own wood burning fireplace after taking in the sights on Going to the Sun Road.

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Waterfront island cabin

Bed & bath:  3 bedrooms, 1 bath Top amenities:  Private lake access, full kitchen, woodburning fireplace Best for:  Water sports with the kids

Ever wanted to run away to your own woodsy island retreat? Well, now you can. This three-bedroom cabin is nestled in a stand of towering pine trees on the western edge of Deer Island, making it the most secluded in the area. Outside, there are massive windows and a wrap-around deck, so you don’t miss a single sunset, while the home’s interior is adorned with colorful southwestern rugs, a wood-burning fireplace, and vintage fishing trinkets. A pontoon boat is available for use while visiting, ensuring you and your loved ones can travel to and from with ease, plus you can rents kayaks nearby for easy exploring.

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Vintage log cabin

Bed & bath:  2 bedrooms, 1 bath Top amenities:  Full kitchen, grill, outdoor dining area Best for:  Artsy couples on a budget

Part of the joy of visiting a national park is immersing yourself in lodging as unique as the landscape. This authentic log cabin was once used by foresters, but has since been transformed into a funky retro wonderland, complete with gingham pillows, red-lacquered dining room chairs, and a private deck with a grill and mountain views. At under 10 minutes from the west entrance of Glacier National Park, this historic Airbnb getaway is the ideal place to snuggle up next to a wood-burning fireplace when your day of exploring is done.

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Meadowlark Treehouse

Bed & bath:  1 bedroom, 1.5 bathrooms Top amenities:  Tempur-Pedic mattress, full kitchen, balcony dining Best for:  Whimsical families and woodsy couples

The Meadowlark Treehouse, crafted around a giant Douglas fir, is where luxury and fairyland collide, all within a 30-minute drive to Glacier. You’ll feel as though you’re tip-toeing through the halls of Hogwarts, ascending a spiral staircase to access the eat-in kitchen, private balcony, and tiled shower, while down below, guests have access to a fire pit, surrounded by Adirondack chairs.

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Luxury lakeside yurt

Bed & bath:  2 bedrooms, 1 bath Top amenities:  Washer and dryer, private deck with grill and gas-powered firepit Best for:  Lakeside lounging

Mountain views abound at this lavish, two-bedroom yurt that’s packed to the brim with chic amenities like Miele appliances, fast Wi-Fi, a private wrap-around deck, fire pit, and stone-encrusted shower. Set on a farm at the northern end of stunning Flathead Lake, this canvas cabin feels like it’s a million miles from the city, while remaining under an hour’s drive to the bustling national park.

best small towns in america Whitefish Montana

Bed & bath:  2 bedrooms, 2.5 baths Top amenities:  Sonos speakers, craft coffee, Bosch kitchen Best for:  Ultra-luxe forest bathing

It’s a challenge to find anything as architectural and elegant as the Nooq in a land populated by antler chandeliers and rustic quilts, and the calming minimalism of this space helps accentuate the already glorious nature right outside the front door. A floating, wood-burning fireplace creates a mod focal point in the open-plan family room, while stainless steel appliances, Danish furnishings, cookware by Le Creuset, and a freestanding tub with mountain views elevate the rest of the space to a luxurious, tranquil retreat.

Where to Stay Near Glacier National Park The Best Hotels Dude Ranches and Glamping Sites

Après Whitefish

Bed & bath:  1 bedroom, 1 bath Top amenities:  Sauna, gear storage, lobby espresso bar Best for:  Adventurous budget-conscious travelers

Après Whitefish prides itself on being a “thoughtfully curated boutique hotel” with wallet-friendly pricing, and we’re here for it. Just opened in 2022, the rooms here are simple yet comfortable, with custom artwork, free Wi-Fi, plush linens, and writing desks, but the communal areas are where Après shines. After a day of hiking to Avalanche Lake, kick back with a locally roasted coffee from the espresso bar, listen to records on a midcentury sofa, or cozy up to new friends around the firepit and in the sauna. If it was up to us, more national park gateway towns would have a hip, young hotel like this.

Where to Stay Near Glacier National Park The Best Hotels Dude Ranches and Glamping Sites

Firebrand Hotel

Bed & bath:  1 bedroom, 1 bath Top amenities:  Rooftop hot tub, ski valet, free bicycle and snowshoe use Best for:  A couples’ spa and park vacay

Amenities abound at this modern oasis situated in the heart of downtown Whitefish. Want to hit a yoga class and then soak in a rooftop hot tub? They’ve got you covered. Hoping to sip bubbly in a cozy igloo with a view? Yep, they’ve got that, too. Guest rooms here are standard hotel fare–clean neutrals, walk-in showers, and well-placed writing desks–but it’s the thoughtful extras, like free airport shuttles, a game library, on-site spa, and ski storage that are truly impressive touches.

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Under Canvas Glacier

Bed & bath:  1 bedroom, 1 bath Top amenities:  Organic bath products, woodburning stove, communal lounges Best for:  Glamping escape with your boo

Set in a tranquil conifer forest, these canvas safari tents offer everything you would expect from a luxe Under Canvas property: organic bath products, rustic wood furnishings by West Elm, and complimentary morning yoga, steps away from the national park. When you’re not lounging on your private deck or enjoying complimentary s’mores, the on-site experience coordinators can help you plan the perfect day inside the park.

Many Glacier Hotel

Many Glacier Hotel

Bed & bath:  1 bedroom, 1 bath Top amenities:  On-site dining, easy lake access, evening ranger programs Best for:  Outdoor lovers who want to stay inside the park

In a park known for its turn-of-the-century lodges inspired by Swiss Alps, the Many Glacier Hotel stands out as the crown jewel of the bunch. Set amidst jaw-dropping views of Swiftcurrent Lake, the property was partially renovated in 2016, though you’ll find no televisions or air conditioning here. Instead, the historic hotel beckons visitors to glean a more old-world experience of the park, with private bathrooms, easy access to dining options, and the same sky-high views of the Northern Rockies that have kept people coming back for generations.

aerial view of The Lodge at Whitefish Lake. pool

The Lodge at Whitefish Lake

Bed & bath:  Varies by accommodation Top amenities:  Gas fireplaces, canoe use, heated pool, lakefront saunas Best for:  Summertime family fun in town and the park

With live music, yoga classes, and a “taprés ski” program (flights of draft beer with slider samplers), it’ll be hard to leave The Lodge at Whitefish Lake in search of some real wilderness. The main lodge building hosts a series of guest rooms, each appointed with a gas fireplace, private balcony, and flat-screen HDTV, while the property also offers a host of more premium options like lakefront condos with full kitchens and spacious luxury homes with floor-to-ceiling windows, pool tables, and soaking tubs.

Wonderstone Glacier

Bed and bath: 1 bedroom, 1 bath Top amenities: Memory foam mattresses, organic linens, flat-screen TVs, complimentary snacks Best for:  Elegant, budget stays

Wonderstone is a newer addition to the Glacier National Park lodging scene, bringing elegant, mountain-modern design and wallet-friendly pricing to Columbia Falls. Guests can choose between a traditional hotel-style room and a hostel-style stay in the building’s bunkhouse. Either way, you’ll enjoy eco-friendly Public Goods bath products, 100 percent cotton linens, complimentary snacks, and free high-speed Wi-Fi (so you can stay connected when you aren’t roaming the many Montana trails).

Where to Stay Near Glacier National Park The Best Hotels Dude Ranches and Glamping Sites

Dancing Spirit Ranch

Bed & bath:  Varies by accommodation Top amenities:  Organic garden, porch views, paddleboards, kayaks Best for:  Traveling families and large groups seeking solitude

Whether you rent the two-person “little white house” or go all out on the seven-bedroom bunkhouse, you’re sure to fall for the inviting down-home charm of Dancing Spirit Ranch. This colorful trio of home rentals is full of rustic design accents (think vintage Persian rugs, rocking chairs, and exposed dark wood beams), plus modern amenities to match, like full bathrooms, organic bath products, and well-stocked kitchens. Best of all? All guests have access to the property’s huge organic garden for pick-your-own fruit and veggie feasts.

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The Green O

Bed & bath: 1 bedroom, 1 bath Top amenities:  Private hot tub, fireplace, included chef-driven meals Best for:  Special occasion couples’ getaway

Tucked into a shady pine grove at the southern edge of the 37,000-acre Paws Up Ranch, The Green O exudes luxury, serenity, and the chance to feel at home in nature, without foregoing a single creature comfort. Each of the 12 “Haus accommodations” possesses its own unique set of amenities—like floor-to-ceiling windows, forested hot tubs, cozy fireplaces, and reading nooks . Add to that the property’s live-fire menu, helmed by executive chef Brandon Cunningham, and a nature-centric spa for when you’ve had your fill, and it’ll be hard to ever want to leave. (Note, this is the farthest lodging option from the park, at about two hours south of the west entrance.)

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Bar W Guest Ranch

Bed & bath:  Varies by accommodation Top amenities:  Included meals, horseback riding, kitchenettes Best for:  Playing cowboy with the fam

A quintessential Montana dude ranch at its core, Bar W seamlessly blends homey western lodging (like framed antlers, bear-accented quilts, and roomy glamping tents) with a full suite of cowboy-centric activities like horseback riding, cattle herding, line dancing, and cookout dinners all included in a package stay. After a day exploring the park's hiking trails and chasing waterfalls inside the park (40 minutes away by car), soothe your tired bones in the property’s bubbling hot tub as a ranch hand serenades you with cowpoke tunes. Bonus: they just added 13 new “cabin suites” in larger log buildings in 2023.

Clydestale Outpost

Bed and bath: 2 bedrooms, 1 bath Top amenities: Cedar hot tubs, trail rides, record players, private decks Best for:  A modern Montana guest ranch experience

First opened in 2022, this horse-centric haven promises “cabins, Clydesdales, and cedar hot tubs.” It’s a delightfully modern take on the Montana guest ranch experience, with lofty ceilings, slate walk-in showers, firepits, and epic private decks at each of the property’s six stately cabins. When you aren’t taking a barn tour or playing giddyup on a trail ride, enjoy each rental’s full kitchen, record player, and private soaking tub with sunset views.

If you're up for a more rugged experience on your next trip, consider camping in Glacier National Park—you can use our complete guide to plan it.

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    The Happy Prince 53' Luxury Yacht Rental Key West Florida. 2 - 8 hours Captained. Up to 10 passengers. $108+ /hour. Stock Island, FL. 4.6 (7 bookings)

  3. Blue Ocean Yacht Charters

    Blue Ocean Yacht Charters, located in Key West, Florida, makes yacht rentals affordable and life-changing. We offer private multi-day bareboat charters to amazing destinations like The Dry Tortugas and the Florida Keys. Just looking for a day charter? Look no further. We offer four hour, eight hour, and 24 hour charters as well multi-day charters.

  4. Yacht & Boat Charters in Key West, FL

    Your hosts aboard Yacht Paradise have recently taken over the operations of Yacht Paradise and Island Vibes Charter boats. We cater to your needs while ensuring your vacation smooth sailing. Our extensive research of the best of the Keys offer a unique perspective on the best ways to spend you vacation. Call Captain Chris at 305.942.0550.

  5. Florida Keys Yacht Charters & Sailing Vacations

    Seven-Day Key West Sailing Itinerary: Embark on a sailing odyssey in The Florida Keys, marked by awe-inspiring sunsets and azure waters teeming with wildlife. The third largest barrier reef in the world offers protected cruising grounds and a spectacle of marine biodiversity.

  6. Key West Yacht Rentals

    Book Key West Yacht Charters. Key West yacht rentals are the very definition of luxury. Whether you're aboard a 45-foot catamaran cruising Key West harbor or sailing the entire Florida archipelago to Key Largo on a 200-footer, every comfort and amenity is provided. From family vacation Key West Sunset to corporate retreat, there's a size ...

  7. Luxury & Private Yacht Charter Key West, FL

    Boat Rental in Key West Renting a boat in Key West is a great choice for a personalized adventure in this tropical haven. With clear waters, rich marine life, and hidden spots, Key West is best explored by boat. A boat rental in Key West, FL, offers the freedom to discover secluded coves, private beaches, and picturesque islands at your own pace.

  8. Anchor: Boat & Captain Rentals, Charters and Water Taxis

    813-906-6064. 260 1st Ave S, Suite 200-183, St. Petersburg, FL 33701. Browse, shop, and compare the best luxury yacht rentals, yacht charters and boat rentals near you. Choose from a list of professional Captains for half-day, full-day, and multi-day yacht charter options. Speak with a live agent now and customize your yacht rental today or ...

  9. Yacht Charter Key West

    Charter Booker carries American Sailing Association certifications and has extensive knowledge of boat safety and regulations. Call 305-923-4152 and ask for "Charter Booker" when booking your next yacht charter with Blue Ocean Yacht Charters in Key West, Florida.)

  10. Catamaran Charter Key West

    Confirmed in 24h. from € 81.283 per week. from $ 91,674 per week. View Details. Catamaran Vacation Rentals in Key West ★ Catamaran Sailing Key West Crewed Catamaran Charters Catamaran Yachts with Captain/Skipper only Bareboat Catamaran Charters for rent in Key West READY TO BOOK ONLINE!

  11. 6 Best Yacht Charters In Key West, Florida

    Panoramic Key West Yacht - 1/2 Off Capt. Charter! Key West, Florida, United States. 2.83 km (1.8 mi) from The Hemingway Home and Museum. 20 reviews. Boat 2 Beds 4 Guests 1 Bedroom 1 Bathroom.

  12. KEY WEST LIVIN' Beautiful 66' Yacht with 4 bedrooms and 4 bath ...

    Situated on the waterfront, this historic houseboat is within 2 mi (3 km) of Key West Harbour, Robbie's, and Lower Keys Medical Center. Key West Golf Club is 1.9 mi (3.1 km) away.

  13. 1 Bedroom Yacht Rental in Key West, FL

    About this rental. Sleeps: 2. Bedrooms: 1. Bathrooms: 1. Property Type: Yacht. Minimum Stay: 2 nights. Living Area: 2000 sq. ft. We specialize in amazing vacations and honeymoon and extended stays for two guests, aboard a yacht that stays dockside without the chance of seasickness allowing you to come and go according to your own schedule.

  14. Key West Yacht Charters

    Sunset Cruises | Day Trips | Multi-Day Charters. The Lisa Lynn is a beautiful 43′ Luxury Charter Boat with 4 staterooms and 2 baths. Lisa Lynn can comfortably host up to 12, and sleep up to 6 passengers. This is the perfect boat to take on a private luxury snorkeling trip to one of our amazing reefs, or a sunset cruise to entertain friends ...

  15. Fun In The Sun ~ Key West Charters & Boat Rentals

    Boat Rentals and Charter Boat Trips with Fun In The Sun in Key West, Fl. Book a trip with our experienced captains or rent your own private boat for the day Phone: (305) 587-3499 Email: [email protected]

  16. Overnight Boat Rental Key West

    Carrying American Sailing Association certifications with extensive knowledge of boat safety and regulations makes him the charter authority. Call 305-923-4152 and ask for "Charter Booker" when booking your next yacht charter in Key West, Florida.)

  17. Key West Vacation Rentals

    Home in Key West. 4.95 (273) Romantic Retreat - 2 person K Suite, Pvt deck/Spa! Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower.

  18. Key West Beachfront Vacation Rentals

    Apartment in Key West. 4.89 (136) Key West Beachside 1400sf, 2 Bedroom Condo. Welcome to our Key West Condo. This spacious well appointed 2 bedroom, 2 bath condo sleeps 6 and is next to the best beach on Key West. This condo is the perfect alternative to staying in a hotel. It gives you a true island experience.

  19. The Crystalmarine Suite

    Romantic getaway on the sea with panoramic views of the ocean. Capture each sunrise and sunset on board this one-of-a-kind, floating vacation suite. Luxurious amenities include a full en suite bath with a rainfall shower head, heated water, A/C, kitchenette, electricity, wi-fi, and even a projector in case you want to "Netflix & chill."

  20. 13 Best VRBO Vacation Rentals In Key West (Cottages, Yachts, & More

    Caroline On My Mind. Caroline On My Mind is a wonderful 2 bedroom condo that features a private balcony overlooking Caroline Street. The second-floor condo is conveniently located just 2 blocks from Duvall Street. Up to 4 guests can be accommodated at this affordable VRBO in Key West.

  21. Florida Keys Boat Vacation Rentals

    4.81 (255) Key West Houseboat Paradise. 56 foot houseboat (1987), Fully Rebuilt in 2022. On a old 15 slip dock on Stock Island, 15 min drive to Key West. Big living room, Full Kitchen, Queen Bdrm + sofa bed. The dock is very local, 'old Key West' sort of vibe with mostly older live-aboard boats.

  22. Top houseboat rentals in Key West

    34' Catamaran Sailboat. Sleeps 4 · 3 bedrooms · 1 bathroom. Explore an array of Key West houseboat rentals, all bookable online. Choose from 35 properties and rent one of the best houseboat rentals in Key West, FL, United States of America for your next weekend or vacation.

  23. Key West Cottage Vacation Rentals

    Nightly prices starting at. $110 before taxes and fees. Find the perfect cottage rental for your trip to Key West. Cottage rentals with a pool, cottage rentals with a hot tub, cottage rentals with free parking, and luxury cottage rentals. Find and book unique cottages on Airbnb.

  24. Key West Bungalow Vacation Rentals

    Bungalow in Islamorada. 4.78 out of 5 average rating, 23 reviews4.78 (23) Islamorada Bungalow 2 Bed/1 Bath & Pool Unit 5. Escape to our charming 2-bedroom, 1-bathroom bungalow in Marathon, FL, where luxury and convenience await!

  25. Where to Stay Near Glacier National Park

    Tucked away in a cabin rental community that's fashioned to look like a Wild West town of yesteryear, Kim's Trading Post is an adorable getaway for those who want the old-school Montana ...