Florida Keys is a place not only for vacationers who love action-filled activities but also for those who seek quietness and relaxation. While active water sports, such as swimming, snorkeling, and kayaking, are a must-try, a day cruise and a sunset sail by the sea will surely relieve your mind and body. Off the coast is Duval Street, a place for historic spots, galleries, and museums, such as Ernest Hemingway Home and Museum. Key West also has many beautiful resorts and hotels. However, if you want to experience morning coffee and late-night drinks while looking at ocean views, check out this list of top yacht charters in Florida Keys, Florida.
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 April 11, 2024.
1. Fully equipped luxury charter boat (from USD 225)
Treat yourself to a relaxing vacation in a 43-foot (13 meters) luxury houseboat styled in wooden tones with 900 square feet (84 square meters) of floor space. The non-smoking cabin has four staterooms that can accommodate up to six people, two bathrooms, and a living room across the galley. The galley is well-equipped and has a dining space good for four. Within the property is a simple pool where guests can refresh for a while.
Top guest reviews
Amenities & 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 viewsCleanliness:
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 waterHost:
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 serviceRead more reviewsLocation:
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 leave
2. Comfortable yacht with full-sized refrigerator (from USD 844)
“License to Chill” is a 55-foot (17 meters) California cockpit motor yacht located in Islamorada. The 950-square-foot (88 square meters) space consists of 2 staterooms with a queen-size bed each, 2 bathrooms, a kitchen with a full-sized refrigerator, and a bright salon.
The rental is an active cruiser, perfect for guests who want to explore the sea. Guests can go fishing and kayaking and play on inflatable toys. Get a relaxing sunbath by the bow and catch a wonderful sunset view from the deck in the afternoon. Breakfast is always included in your stay, and an onboard dinner on your first night is nicely prepared by the captain.
Top guest reviews
Amenities & Room:
providing adequate space and creature comfortsThe yacht was very roomyOur flight was delayed 3 hours and instead of a sunset cruise as plannedThe yacht was cozy but still had two staterooms and 3 headswould whip up the best meals with easeCleanliness:
everything so clean and comfy so beautifulHost:
they gave us a morning cruiseshe was amazingly fast in everything she didthey are awesome taking care of us all the timeAfter we boarded Kenny and Monica gave us a fantastic welcome with a tour of the yachtprecioso tiene dos habitaciones super comodasRead more reviewsLocation:
la limpieza extrema la atencion de los duenosThe License to Chill boating experience was top notches super se quedan contigo pendiente de lo q necesites todo el tiempo en la noche que estuve ahi pasamos un momentola cama las almohadas el colchonFrom the moment we stepped aboard we felt comfortable and attended to in every way possible
3. Beautiful accommodation with spacious salon (from USD 160)
“Island Yacht Adventures” is a 40-foot (12 meters) houseboat anchored in Blackfin Marina, Marathon Island. Inside the master bedroom are a queen-size bed and a private bathroom. The yacht has a full-set galley and a wide salon furnished with a long couch and a TV. Included in the stay is a continental breakfast provided by the host.
Outdoor activities to explore in the marina are kayaking and swimming. Guests can make use of a barbecue grill beside the gazebo. The place has a swimming pool area and a sunset-viewing patio at the marina point. Guests can avail a day cruise at an extra cost.
Top guest reviews
Amenities & Room:
you can enjoy your coffee on the deck and annette always prepares us breakfast in the morningthe bed plenty large and the mattress comfy the salon was comfortable with plush sofaswe also loved how clean our room was and all the amenities the boat had to offerthe stateroom we had was clean comfortable quiet and had its own a/c control and bathroomCleanliness:
everything was clean including the marinathe room and bathroom was clean and privatethe accommodations are very clean and cozythe place was immaculate smelled fresh and everything you needed was therethe shower had great pressure and hot water and the bathroom was spotlessHost:
best hosts by farwonderful hosts and great experiencethe kayaks were very nice to have the hosts are super friendlythey were very thoughtful and accommodatingthey are very kind and as everyone has said make you feel right at homeRead more reviewsLocation:
the location is awesomethe location is so perfectand the location was excellentgreat location at end up herethe dock is in the perfect location in that it is central to everything that you could need
Superhost
4. Well-lit yacht with underwater windows (from USD 760)
Docked on a 5-star resort is a 4-bedroom luxury yacht that can accommodate up to 11 persons on board. All four staterooms have a private bathroom and a queen-size bed. An additional single bed is placed in one of the guest’s staterooms. Both guest rooms have underwater windows that offer a nice view of marine life in the calm water. What’s more, the kitchen and living room are well-lit and are fully furnished.
Guests will have access to the resort’s waterfront swimming pools, fitness center, and restaurants. Laundry and bath showers are available at the marina. Free shuttle service to and from downtown Key West is provided in the marina for convenience.
Top guest reviews
Amenities & Room:
the marina restaurants pools and facilities were perfectthe new marina (stock island) was definitely the better place withbathrooms showers bar pool hotel ect etcplenty of room for more aswellCleanliness:
more importantly it was beautiful clean and everything we could haveasked forthe stock island marina is pristine - incredibly clean and well keptthe boat was clean comfortable and well-equippedrooms were clean and comfortable and our party of 10 had plenty of space to maneuver aboutthe boat was clean easy to locate items and most important comfortableHost:
every member of the staff we met were super nice and helpfulespecially for watching the big football game sunday night everyone we encountered was very friendly and helpfultim & his team were professional responsive and easy to work withRead more reviewsLocation:
the hotel is in walking distance with free shuttles to areas on key west great pool and fantastic restaurant
5. Lovely catamaran with spacious galley (from USD 1000)
On the coast of the Key West area is a 38-foot (12 meters) sailing catamaran named Papillon. Four persons can sleep in the vessel’s three cabins, two of which have queen-size beds while the other has a single bed. Two bathrooms are available inside, one with a shower and the other with a composting head. Meals can be conveniently prepared in the spacious galley with a complete kitchen set. As for dining, guests can enjoy a six-seating area inside or at the cockpit outside with a nice water view.
All meals, including snacks and beverages for guests, are included in the stay prepared by the host. Water activities to explore are snorkeling, kayaking, and swimming. Upon request, a day trip to Duval Street and known Key West landmarks can be accommodated by the host.
Top guest reviews
Read more reviewsAmenities & Room:
very comfortable quarters for 6 people both on and under the deck
6. Family-friendly sailboat with pool access (from USD 500)
“Lady Christine,” a 30-foot (9 meters) sailboat, is a nice and cozy place for a family of four. The space is furnished with an aft berth and v-berth alongside the galley. For kids, the dinette area can be converted to a bed. The galley is equipped with essentials for an easy time cooking and dining.
Within the marina, guests are entitled to use the outdoor pool, fitness center, bathhouses, and laundry facilities. Fascinating delicacies are also served in the restaurants around the marina.
Top guest reviews
Amenities & Room:
the amenities of the hotel 2 very nice pools 2 restaurants and a bodega were fabulousthe pool and outside bar & grill was nicebeds were comfy & the ac worked great loved the availability/proximity of bathrooms/ shower/pool/barhaving 2 pools a couple of restaurants and an outdoor sports bar to choose from was perfectCleanliness:
clean bathrooms and nice swimming pool areathe boat was clean and comfortable for the two of usthe boat is so clean and amazingthe shower/ bathroom facilities were cleanHost:
steven is a great hostthe boat and host are greatsteve was an awesome host with quick responsesvery unique experience in the keys steve is a great hostgreat host very clear and comfortableRead more reviewsLocation:
the location was amazingwe would definitely recommend this locationsuch a cool location at the marinathe location is very convenient and safethe closer pool (45 second walk) is quieter and more peaceful
7. Spacious catamaran sailboat with an aft salon (from USD 317)
Explore the best beaches of Key West in this catamaran sailboat that comes with a single luxe bedroom. Within the room are a king-size bed, a separate toilet and shower room, a library, and a workspace. The amenities outside are a perfect match with the waterfront view. An aft salon with comfortable seating and a table is a nice place to enjoy the ocean breeze.
Meanwhile, bow seats and a trampoline on the deck are great for sunbathing and watching marine animals. The roof deck is a fun place to savor an alfresco continental mimosa breakfast prepared by the host. The sailboat is docked at a marina resort, which comes with a pool, restaurants, and bars that guests can enjoy. Water activities such as snorkeling, swimming, and kayaking are welcome upon request.
Top guest reviews
Amenities & Room:
the pools were greatpools and restaurant were very nicewe did use the bathrooms pools and the food at the dock was deliciousthe fresh breakfasts and coffee each morning were wonderfulthe room we stayed comes with a nice king bed and is very comfortableCleanliness:
the space was clean cozy and comfortableour room was clean and to our surprise very roomythe room is small so pack lightly but it’s clean and the bed was very comfortablethe boat was clean and welcomingboat was super clean and the whole experience was awesomeHost:
they were great hostour hosts made us feel very welcome and comfortablethey are a friendly host that is willing to accommodate if you have a special requestfred and marsha were delightful hosts - we thoroughly enjoyed our staygreat hosts great marina great timeRead more reviewsLocation:
positive: the location is beautiful and fred is very personable and shares good information about the area
An ocean adventure in the finest islands of Florida
The dazzling islands and clear waters of Florida Keys will never disappoint every vacationer. Water adventures, marine life tours, and sunset sails are some of the best ways to unwind, and this island offers just that. Have a memorable stay on one of the top yacht charters for your fun-filled and relaxing getaway.
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