Key West is an island city in the Florida Keys, famous for its upscale beach lifestyle and many exciting things to do at night. It’s popular among beach lovers and water sports enthusiasts alike. The best way to experience this tropical oasis is on the water, and the best option is to stay on a private overnight boat charter to fully capture all possible opportunities to dip into the crystal blue ocean. Warmed by the gulf stream, the water in Key West maintains a perfect year-round temperature for swimming, snorkelling, diving and more. The area’s warm tropical climate also makes it irresistible to cool off in the refreshing ocean. For your next trip, read on to find out the best yacht charters in Key West, Florida, for a memorable adventure.
Events to look out for
Grown-ups can surely not miss the annual 10-day long Fantasy Fest where revelers can pour in their creativity and participate in costume parades and other activities.
Travelers visiting in July can participate or attend the Annual Hemingway Look-Alike Contest, which will be celebrating its 43rd edition in 2024. Some of the features of this event include a look-alike contest, where participants will be judged on their appearance and ability to match Papa Hemingway.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on October 24, 2025.
1. Happy's Houseboat
This private yacht charter in Key West is perfect for a couple seeking a unique getaway on the water. Anchored in an enclosed bay, this houseboat has a spacious main suite and a well-equipped kitchen. The large sun deck is great for suntanning in the day and stargazing at night. Guests can just hop off the deck into the warm waters of the Florida Keys and have a swim or snorkel with the marine life. Kayaks, paddle boards and bicycles are available for rent for an additional fee. The host is also happy to bring guests out to secluded swimming, fishing and snorkelling spots, so please do put in your request when making reservations.
Key West, Florida, United States
3.1 km (2.0 mi) from The Hemingway Home and Museum
Top guest reviews
Read more reviewsLocation:
amazing location in the middle of the bay very private with great views on every side
2. Fantastic yacht in downtown Key West
Maximize your Key West adventure by actually living by the seas in this stunning yacht accommodation. The boat is chic, elegant, and complete with necessary amenities to make your stay comfortable and convenient. It has two bedrooms and two private bathrooms that can comfortably accommodate four guests. This boat is conveniently docked in the marina in downtown Key West where guests have access to a plethora of excellent restaurants, retail shops, and the city’s top attractions. It is fully air-conditioned, pet-friendly, and has a provided parking space for guests traveling by car.
Key West, Florida, United States
1.11 km (0.7 mi) from The Hemingway Home and Museum
Top guest reviews
Host:
The crew members were super professional yet so friendlyThey made us feel like we were out with friends and not a hired crewAlbert our host was very friendly and welcoming and made sure to stop by and make sure we were happy with our overall stayWe had a couple issues early on (happens with any boat)The Captain and crew could not have been more friendly and helpful - for anyone who chooses to stay hereLocation:
Location was great close to restaurants shops and the downtown area sailing to The ReefWhat an incredible location just steps away from bars restaurantsThe location was close to all the fun of Key West and felt miles away tooshopping fishing etc Can walk to basically any serviceWe live in Fort Lauderdale so not too far of a drive to come back Thanks againRead more reviewsAmenities & Room:
Had a great time more than expected treated like familyWill be backwas the highlight Of our tripThe boat was larger than we expected and had everything we needed to feel at homeaccess to the piers private bath/shower/laundry is a BIG PLUS FaleaciaThe boat is what it says it is
3. Sailboat near downtown Key West
If you are traveling to the beautiful island city of Key West any time soon and you are not into the crowded hotel living setup, you might want to try living in the seas in this gorgeous yacht. It is located in Downtown Key West where all the attractions, including exquisite restaurants and souvenir shops, are also situated. On the other hand, this yacht features two delightful bedrooms and two fantastic bathrooms. It has electricity and air-conditioning. Plus, it is available for charter at an additional cost.
Key West, Florida, United States
6.34 km (4.0 mi) from The Hemingway Home and Museum
Top guest reviews
Host:
she is definitely a sweetheart and was very helpfulthe accommodations were excellent the crew and owners fantastic and key westfirst let me say how pleasant albert and rhonda are as hostscaptain and crew were very friendly and helpful and great about teaching our boys about sailingLocation:
we really enjoyed the stay aboard and the convenient locationthe location is excellent and you can’t beat watching the sunset while sipping a cocktail on decklocation is ideal close to everything even restaurants and coffee shops at the end of the dockCleanliness:
the boat was clean and quite comfortablethe marina restroom and showers were very clean and convenientRead more reviewsAmenities & Room:
it has two bedrooms two small bathrooms and a nice center cabin with a kitchenette and seating areathe master stateroom was very nice with a most comfortable bed
4. Transformed classic Bluewater Cruiser offering mesmerizing views of the bay (from USD 313)
This transformed classic Bluewater Cruiser is now your cosy and stylish sanctuary, offering mesmerizing views of the bay, canal, and sandy beaches. Hop aboard the 45-foot (13.72 meter) yacht, featuring a roomy main cabin with a cushy memory foam queen bed and refreshing ocean breeze. Enjoy the fully equipped kitchen, speedy Wi-Fi, and TV entertainment. Head to the upper-level bridge with comfy cushions and a dining set to relish the stunning scenery.
Exciting extras include kayaks, a full bar, and a shuttle service to and from shore. Get ready for thrilling captained yacht charters for fishing, snorkelling, and exploring Key West Sand Bars or Dry Tortugas.
Key West, Florida, United States
2.83 km (1.8 mi) from The Hemingway Home and MuseumAccommodates: 4
Top guest reviews
Host:
the hosts went out if our way to make our stay comfortableeverything went smoothly and ali was incredibly kind and easy to work withali and larry were great hosts offering help when we neededamazing sunrises and sunsets ali and her husband were extremely helpful and were outstanding hoststhese are the best hostsRead more reviewsAmenities & Room:
we made breakfast almost every morning and loved coffee out on the bowit was peaceful had unbelievably stunning beauty and was very comfortable
5. Unique stay out at sea (from USD 264)
Ideal for an adventurous couple, the Wanderland is a 50 feet (15 metres) pleasure craft moored in an amazing location, out at sea, where beautiful sunsets are guaranteed. Jump right off the vessel into the welcoming waters to snorkel, kayak, fish and paddle board ⎯ this makes for a dream vacation for water sports enthusiasts and ocean lovers alike. Staying on the Wanderland is a little like camping but out on the ocean. Guests must bring food and drinks for their days on the boat. The barbecue onboard is perfect for grilled dinners while enjoying the amazing sunsets.
Key West, Florida, United States
1.35 km (0.9 mi) from The Hemingway Home and MuseumAccommodates: 6
Top guest reviews
Host:
robert and his crew were very helpful throughout our staythe space was comfortable the people were so kind knowledgeable and were so accommodatingvery friendly hostscomfy beds there were some minor hiccups with the boat but robert was an amazing host responsive and friendlyit’s so spacious and private robert was such a great host and was always a call awayLocation:
great location great boat great for adventurerstowards key west there are quite a few boats but they are not terribly closeRead more reviewsCleanliness:
hopefully they will repair the broken window and clean and disinfect the place before other guests arrive
Nearby yacht rentals
6. Exquisitely crafted vessel designed for pure relaxation (from USD 565)
Step aboard this exquisitely crafted vessel designed for pure relaxation, ideal for a couple seeking a touch of luxury. Drift off to dreamland on a sumptuous front bed adorned with cozy blankets and soft pillows. The living area beckons you to unwind, offering a fold-down table for dining or just chilling out. Need more space? No problem! Tuck in for the night with additional sleeping options cleverly concealed in the back cushions.
Beach lovers will adore the direct access, while a shared outdoor pool promises a delightful oasis. Adventure-seekers, you’re in for a treat with complimentary kayaks, beach cruisers, and snorkel gear at your disposal. Even your furry friends are welcome! Cook up scrumptious meals in the well-equipped kitchen boasting an induction stove, microwave, and grill.
Key West, Florida, United States
6.97 km (4.4 mi) from The Hemingway Home and MuseumAccommodates: 4
Top guest reviews
Host:
david was a great host with plenty of knowledge of the areadave was a great host the boat was perfect for a short little getawayfriendly hosts neighbors and dock dogRead more reviewsLocation:
close to everything fun in key west and the other keysi fun unique place to staygreat place to stay if you want to experience what boat life is like
7. Deluxe charter boat for a group of six
Moored at a small local marina, this luxury yacht charter in Key West offers a live-aboard experience that will have you feeling like a local yachtie. The yacht has four staterooms that can accommodate up to six guests and is equipped with all the basic amenities. The marina is home to local artists, who display their work throughout the quay. There is a fantastic seafood restaurant serving up delicious local catch just a few steps from the yacht. The restaurant also hosts live entertainment every Friday and Saturday, which is a great opportunity for meeting the artsy locals.
7.01 km (4.4 mi) from The Hemingway Home and MuseumAccommodates: 6
Minimum Nights: 3
Refund Policy :
Top guest reviews
Host:
and he answered us right awayhe's an awesome guyVery friendly marina Would returnAndy was very quick to respond to the couple questions we had when we checked inThe Hogfish Bar and Grill (almost next door) is fantastic Good food drinks and serviceLocation:
Enjoyed learning this way of lifeAlso ate at Roostica Pizza on Stock Island - another great choice Thanks for everythingIt is a little ways away from Duval Street in Key West but was very easily accessed by Uber for approximately $20If" a problem arises Andy takes care of it immediatelySpent the entire month of February here and didn't want to leaveCleanliness:
Loved it very cleanThe boat was very clean and well maintainedThe boat house was quite sufficient for showering water pressure was great and always had hot waterRead more reviewsAmenities & Room:
The boat is very spacious Beds are not plush but your on a boatThe pictures on the listing are exactly as the boat looked in personThe yacht was beautiful and immaculatewe did not use)We sat at the top of the boat and had beautiful views
8. Exceptional boat rental for six guests
Experience Key West’s luxurious lifestyle by living in a yacht during your adventure to this beautiful island city in Florida. It bills itself as an accommodation better than any hotel in the city. Docked on a safe harbor with breathtaking views, guests have easy access to lots of attractions within the area, including excellent restaurants and laidback cafes. On the other hand, this yacht features three comfy bedrooms and two private bathrooms. It also has a kitchen with cooking essentials and basic appliances, a dining area, and a cockpit with seating.
Key West, Florida, United States
6.98 km (4.4 mi) from The Hemingway Home and Museum
Top guest reviews
Host:
/everyone was so accommodatingNice boat in an amazing marinaOwner and arrival well planned Very accessable - helpful when we first arrived and getting settled in Great recommendations given for local activitiesthe marina is beautiful and the ownerthe owner Alex checked in with us to make sure everything was going well Would definitely recommendLocation:
it was fun good location and great amenities but general cleaning of a placeUnfortunately it did not measure upand we were looking for something differentFound this boat that looked wonderful and something differentcaught a lot of Snapper to cook up on the grill at the end of the dockCleanliness:
Everything looks exactly as pictured if not betterThe boat was super cleanVery nice stay on the boat very quiet and clean CloseIt was very spacious and had everything we needed right thereThe boat was exactly as described and had MORE than enough room for all of guestsRead more reviewsAmenities & Room:
I chose to use the shower down on the same dock instead of on boathad all amenities we needed AC very cold and flatscreen tv to watchit had everything we needed from toiletries to kitchen utensilsit accommodates every need for a great stay Having the options of three bedrooms plus a pull-out in the living room allowed us to not only spend time with multiple friends but also feel comforta...Had the captain take us our one day
9. Sail boat with a fabulous cockpit lounge area
Looking for a big, spacious accommodation for a group of eight? If so, this lovely boat rental is a fantastic choice for you. It is elegant, luxurious, cozy, and complete with upscale amenities that will surely make your Key West adventure unforgettable. The boat features three comfortable bedrooms, three sparkling clean bathrooms, and a full kitchen where you can prepare your specialty dishes. Its cockpit is turned into a fabulous lounge area where you can enjoy after-hour drinks as you watch the sunset with the cotton candy skies in the background.
6.4 km (4.0 mi) from The Hemingway Home and MuseumAccommodates: 8
Minimum Nights: 90
Refund Policy : 100% refund if you cancel at least 14 days before check-in.
Top guest reviews
Host:
met all of our needsthe marina was beautiful as well we have been visiting the keys for yearsour start was a little bumpy but ray was great to work with if we needed anything or had questions he was a big helphad the boat well prepared for us and was only a call away when we threw a breaker while running the microwave oven and brewing coffee at the same timethe manager was also very nice and accomodatingLocation:
The shuttle is a great way to get aroundWe also did eat at a few of the restaurants recommended by Guy FieriWe did eat at a few of the restaurants recommended by Ray (which was a short drive to Key West)We rented scooters and was able to get around town easilyIt was a new experience - very different from any otherCleanliness:
Very nice and quiet Very relaxing vacationThe three bedrooms were adequate for adults and air conditioningRead more reviewsAmenities & Room:
Lucy had plenty of room for our lounging around and cooking Raybut that was preplanned at the request of the kidsIt was our first time in Key West and we enjoyed our staythe boys had a blast fishing right off the boat and dockIt was very comfortable and had all the accommodations we needed
10. Motor yacht with mod cons (from USD 1120)
Live like a celebrity on this motor yacht and experience the exclusive lifestyle at its premium marina. This pleasure yacht can sleep up to six guests comfortably in its three rooms. It also has spacious indoor and outdoor living areas, roomy enough for everyone to spread out. It is moored at one of the best resorts in Key West, The Perry Hotel, which has luxurious waterfront swimming pools, fine dining restaurants, free shuttle service to town, and more. While the vessel will be moored during your stay, guests will be requested to book a cruise package during the reservation period to discover the beautiful ocean around Key West.
Key West, Florida, United States
6.3 km (4.0 mi) from The Hemingway Home and MuseumAccommodates: 7
Top guest reviews
Cleanliness:
the marina was wonderful the pool bar and bathrooms were cleanRead more reviewsAmenities & Room:
the marina was wonderful with great amenities a beautiful pool shuttle and at night it was peaceful
Stay on the water in Key West
Explore Key West like a local and spend your days lounging on a luxury yacht and exploring best places to eat. The ocean is Key West’s best feature and there is nowhere closer to the water than staying in one of these best yacht rentals in Key West.
Frequently asked questions about yacht charters in Key West
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