Top 7 Yacht Charters In Florida Keys, Florida - Updated 2024

Nicole Ann
Nicole Ann 
| 5 min read

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.

Stayed at this property?

7.01 km (4.4 mi) from The Hemingway Home and Museum
82 reviews  
yacht 6 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 3
Refund Policy :

Top guest reviews
Amenities & Room:
The boat is very spacious Beds are not plush but your on a boat
The pictures on the listing are exactly as the boat looked in person
The yacht was beautiful and immaculate
we did not use)
We sat at the top of the boat and had beautiful views
Loved it very clean
The boat was very clean and well maintained
The boat house was quite sufficient for showering water pressure was great and always had hot water
and he answered us right away
he's an awesome guy
Very friendly marina Would return
Andy was very quick to respond to the couple questions we had when we checked in
The Hogfish Bar and Grill (almost next door) is fantastic Good food drinks and service
Enjoyed learning this way of life
Also ate at Roostica Pizza on Stock Island - another great choice Thanks for everything
It is a little ways away from Duval Street in Key West but was very easily accessed by Uber for approximately $20
If" a problem arises Andy takes care of it immediately
Spent the entire month of February here and didn't want to leave
Read more reviews
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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.

Stayed at this property?

153.22 km (95.3 mi) from The Hemingway Home and Museum
28 reviews   Wifi Available
yacht 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
providing adequate space and creature comforts
The yacht was very roomy
Our flight was delayed 3 hours and instead of a sunset cruise as planned
The yacht was cozy but still had two staterooms and 3 heads
would whip up the best meals with ease
everything so clean and comfy so beautiful
they gave us a morning cruise
she was amazingly fast in everything she did
they are awesome taking care of us all the time
After we boarded Kenny and Monica gave us a fantastic welcome with a tour of the yacht
precioso tiene dos habitaciones super comodas
la limpieza extrema la atencion de los duenos
The License to Chill boating experience was top notch
es super se quedan contigo pendiente de lo q necesites todo el tiempo en la noche que estuve ahi pasamos un momento
la cama las almohadas el colchon
From the moment we stepped aboard we felt comfortable and attended to in every way possible
Read more reviews
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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.

Stayed at this property?
Marathon, Florida, United States
74.68 km (46.4 mi) from The Hemingway Home and Museum
393 reviews   Superhost Wifi Available
Private room in boat 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
you can enjoy your coffee on the deck and annette always prepares us breakfast in the morning
the bed plenty large and the mattress comfy the salon was comfortable with plush sofas
we also loved how clean our room was and all the amenities the boat had to offer
the stateroom we had was clean comfortable quiet and had its own a/c control and bathroom
everything was clean including the marina
the room and bathroom was clean and private
the accommodations are very clean and cozy
the place was immaculate smelled fresh and everything you needed was there
the shower had great pressure and hot water and the bathroom was spotless
best hosts by far
wonderful hosts and great experience
the kayaks were very nice to have the hosts are super friendly
they were very thoughtful and accommodating
they are very kind and as everyone has said make you feel right at home
the location is awesome
the location is so perfect
and the location was excellent
great location at end up here
the dock is in the perfect location in that it is central to everything that you could need
Read more reviews

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.

Stayed at this property?

6.54 km (4.1 mi) from The Hemingway Home and Museum
60 reviews   Wifi Available
yacht 9 Guests 4 Bedrooms 5 Bathrooms

Accommodates: 9
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the marina restaurants pools and facilities were perfect
the new marina (stock island) was definitely the better place withbathrooms showers bar pool hotel ect etc
plenty of room for more aswell
more importantly it was beautiful clean and everything we could haveasked for
the stock island marina is pristine - incredibly clean and well kept
the boat was clean comfortable and well-equipped
rooms were clean and comfortable and our party of 10 had plenty of space to maneuver about
the boat was clean easy to locate items and most important comfortable
every member of the staff we met were super nice and helpful
especially for watching the big football game sunday night everyone we encountered was very friendly and helpful
tim & his team were professional responsive and easy to work with
the hotel is in walking distance with free shuttles to areas on key west great pool and fantastic restaurant
Read more reviews
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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.

Stayed at this property?

7.6 km (4.8 mi) from The Hemingway Home and Museum
23 reviews  
yacht 4 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 4
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
very comfortable quarters for 6 people both on and under the deck
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

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.

Stayed at this property?
Key West, Florida, United States
6.51 km (4.1 mi) from The Hemingway Home and Museum
182 reviews   Wifi Available
Boat 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the amenities of the hotel 2 very nice pools 2 restaurants and a bodega were fabulous
the pool and outside bar & grill was nice
beds were comfy & the ac worked great loved the availability/proximity of bathrooms/ shower/pool/bar
having 2 pools a couple of restaurants and an outdoor sports bar to choose from was perfect
clean bathrooms and nice swimming pool area
the boat was clean and comfortable for the two of us
the boat is so clean and amazing
the shower/ bathroom facilities were clean
steven is a great host
the boat and host are great
steve was an awesome host with quick responses
very unique experience in the keys steve is a great host
great host very clear and comfortable
the location was amazing
we would definitely recommend this location
such a cool location at the marina
the location is very convenient and safe
the closer pool (45 second walk) is quieter and more peaceful
Read more reviews

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.

Stayed at this property?
Key West, Florida, United States
6.39 km (4.0 mi) from The Hemingway Home and Museum
93 reviews   Wifi Available
Private room in boat 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the pools were great
pools and restaurant were very nice
we did use the bathrooms pools and the food at the dock was delicious
the fresh breakfasts and coffee each morning were wonderful
the room we stayed comes with a nice king bed and is very comfortable
the space was clean cozy and comfortable
our room was clean and to our surprise very roomy
the room is small so pack lightly but it’s clean and the bed was very comfortable
the boat was clean and welcoming
boat was super clean and the whole experience was awesome
they were great host
our hosts made us feel very welcome and comfortable
they are a friendly host that is willing to accommodate if you have a special request
fred and marsha were delightful hosts - we thoroughly enjoyed our stay
great hosts great marina great time
positive: the location is beautiful and fred is very personable and shares good information about the area
Read more reviews

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.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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I'm a Filipina Chemical Engineer with a passion for writing and a dream to travel and explore different places. Since high school, I have loved the writing world, and it's something I want to build...Read more

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