Rent A Boat In Florida Keys - Updated 2022

rent a boat in the keys

Undoubtedly one of the best destinations in the Sunshine State is Florida Keys, an archipelago made up of coral cays in the southern tip of Florida, close to Cuba. The largest and most inhabited of the islands is Key West, but there are many other isles to see, both inhabited and uninhabited. Renting a boat is one of the best ways to explore and experience everything about Florida Keys, from the small towns to the amazing snorkeling and fishing these turquoise waters have to offer. Being on a boat isn’t everyone’s cup of tea but if you’re eager to outgrow your sea legs, here are several accommodations that might convince you to rent a boat in Florida Keys, Florida, USA.

1. Green-powered sailboat in Islamorada (from USD 200)

For the environmentally-conscious who wants to explore the Keys without the carbon emissions, this is the perfect sailboat for you. This private retreat on the water runs on wind and solar energy, enough to power the boat’s refrigerator, TV, and freezer. Other essentials you’ll find onboard include a full kitchen, a compost toilet and shower, and a queen bed. Outside, there’s a roof deck with a grill and space enough to get a suntan. This houseboat is best if you want to make the most out of your stay in Islamorada, as there are a couple of restaurants and other island treats located near the dock.

Islamorada, Florida, United States
252 reviews Superhost  Wifi Available
Boat 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
wifi single is good
great views and comfortable amenities
" the boat has a stove fridge bathroom shower and even a/c everything you need for a perfect weekend
the cool shower felt perfect after a hot day
it was super clean
the houseboat was clean and well stocked with everything we needed
linda is an excellent host
linda was a great host
linda was an awesome host very quick responses to all of our questions
linda is a gracious informative host
linda is a great host and very accommodating
several good restaurants close to this location
great location just a few minutes off shore
it's a gorgeous location and very private
amazing houseboat in great location
beautiful location so relaxing and wonderful in every way
Read more reviews

2. Romantic sailboat with cozy salon (from USD 129)

This 38-foot (11.6 m) sailboat is a great option if you want to make some memories sailing around the Keys. You’ll be taken to and from the dock on a smaller boat to board this beauty, where you’ll be greeted by the host. This boat is best for those over the age of 18, perfect for you and two other friends. There’s a nice and comfortable salon inside, two cozy beds good for three, a coffee maker, an electric toilet and a sink. If you want to explore any of the islands on land, there are two bikes free for the guests to use.

Key West, Florida, United States
436 reviews
Boat 2 Beds 3 Guests 1 Bedroom 0 Bathrooms

Accommodates: 3

Top guest reviews
Amenities & Room:
it is like camping so don’t expect any air conditioning/electricity/running water
it was extremely comfortable and the rocking of the waves made sleeping amazing
you cannot take shower but the boat is equipped with everything you need (electricity fresh water blankets etc)
i think the boat is pretty clean and doesn’t have smell as in another review
the boat was clean had plenty of space coffee tea clean blankets and sheets
the boat is clean and comfortable
the interior was cozy and clean with fresh sheets and pillow cases for us
mike does a great job of cleaning it provides fresh sheets water & coffee
mike was an outstanding host
mike is a great host and captain
thank you for the experience mike you were a great host
he’s knowledgeable and friendly and we can’t thank him enough
mike is a fantastic host who’s friendly and knowledgeable about things to do in the area
it's a very nice location ideal to spend a day on the ocean
i would definitely recommend this location for anyone that wants to experience key west in a different way
mike's boat is in a wonderful location out in the water
mike's boat is at a great location remote from the noises and it is so peaceful
i love camping and this was as close as you could get while being on the ocean
Read more reviews

3. Spacious cabin cruiser with hot water

Speed off to the Key Largo sunset in this snazzy Sundancer cabin cruiser named Serenity. It has hot running water in the bathroom so you can start the day feeling fresh and rejuvenated. Serenity is docked in a private area, with access to a charcoal grill and a patio table with chairs. This is the perfect boat for fishing trips as the hosts will also provide you with rods and an array of tackle. On land, you can walk just a little further to find a tiki bar and enjoy some drinks at sundown.

Yacht in Key Largo, Florida
Key Largo, Florida, United States
382 reviews
Boat 2 Beds 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
ice cold ac and nice not water for shower
the bed was very comfortable and the ac worked great
the inner cabin was flawless and beds were very comfy
nice having breakfast on the “porch” back end of the boat with the water views
the bed super comfy
very clean and stocked with everything you need
we found it to be clean and prepared
nice and clean accommodation special place to spend the night
the cleanliness of the main outside cabin is an issue with the inside being generally clean
the place was clean quiet and just a fantastic place to relax
the hosts were awesome
david was a great host
olivia and will were great hosts
our host was so kind and attentive to our every need
the owner very responsive and helpful check in and out went smoothly
great location off the beaten path
great location with everything you need right there
amazing time the location was perfect
great location on a quiet shoreline
great location-excellent food and drinks at the blackwater siren
Read more reviews

4. Pet-friendly houseboat for four

This boat is suitable for a larger group and perhaps a furry friend! It has everything a party of four needs: a walk-around bed, a deluxe twin mattress, and a daybed so everyone can sleep comfortably. There’s also an upper deck where you and your loved ones can enjoy cocktails at sunset. The host has also provided a kayak and a paddleboard, both of which you’re free to use. Your spot on the dock is close to a bathhouse, several tiki huts and, of course, the beach. Pets are welcome to stay aboard for an additional fee, so you can bring your furry companion along on the trip.

houseboat in paradise with beach
Key Largo, Florida, United States
245 reviews
Boat 3 Beds 1 Bedroom
Top guest reviews
Amenities & Room:
comfortable couch and bed and cool sleeping space for kids under the helm
he loved it and there was a fan to help with air circulation
yet has excellent wifi/cell service for work/communication
bed was comfy and the big couch is awesome
the houseboat was very comfortable for us
the boat was very clean the towels smelled fresh and clean as did the sheets
everything was clean and in good working order
they kept it very clean
the shower house/bathrooms are kept extremely clean as well
we absolutely had everything we needed and the bathhouse was very clean and convenient
abigail is a great host
abigail was an awesome host
abigail was the best host we have ever had
the owners of the surrounding boats are so friendly
visitors can expect a friendly host who responds in a timely manner and provides useful advice to her clients
amazing location and wonderful place
the location is wonderful secluded yet everything you need is close by
location was great - near many bars and restaurants which were walkable
the location is amazing 100% worth it
thanks great experience and location
Read more reviews

5. No-frills sailboat with free kayak

Sailing can either be a luxurious or an adventurous experience, and sometimes it can be both. But if you’re more of a backpacker with simple needs and a desire to experience sailing around the Keys, this boat is perfect and budget-friendly. Since it’s moored on a shallow channel, you’ll need to kayak to the sailboat, so best pack light! Aboard the Mangrove Ninja, there’s a comfortable mattress, a solar-bag shower, a porta-potty with curtains for privacy, and a cooler for your snacks and drinks. Don’t worry, you won’t be completely roughing it - you’ll be treated to a million-dollar view in every direction.

Small, Peaceful Sailboat w/Kayak (s)
Key West, Florida, United States
309 reviews
Boat 2 Beds 0 Bathrooms
Top guest reviews
the boat was clean and the towels and linens smelled snuggly fresh
great host and stay
zappa was an awesome host
hosts are the best as well
great spot and very kind hosts
beautiful spot and the hosts were very nice people
the boat location is amazing close to everything you need
nice people and location
sweet little place floating in the middle of paradise
we were able to park right by our launch site and drive around town with ease
very relaxing environment and only a paddle away to the closest bar
Read more reviews

6. Cute sailboat for the solo traveler

It’s nice to get away every once in a while, so if you want some guaranteed time alone, this sailboat is perfect for you. It’s budget-friendly and equipped with all the essentials: safety gear including life jackets, small battery-powered fans, a cooler for snacks and refreshments, fresh bed linens and towels, a porta-potty, solar shower, and toiletries. This cute sailboat also comes with a kayak, which you’ll use to board and disembark. You can explore the nearby mangroves, or stay moored and stargaze. It’s up to you!

Cute Budget Traveler Sailboat with Kayak(s)
Key West, Florida, United States
195 reviews
Boat 2 Beds 1 Bedroom 0 Bathrooms
Top guest reviews
the bed was comfy and the cabin was clean and stocked with anything you might need
zappa and amber are very friendly and hospitable the boat was clean and had everything you might need
the sailboat was very clean and everything on it functioned as it should
your clean clothes will feel salt-chapped and perpetually damp
really nice boat and zappa is a great host
the hosts were very friendly and accommodating
zappa is a great host
on the boat zappa informed us friendly about how everything works
they were very thoughtful helpful and down to earth
beautiful location w many prime kayaking spots
the location was perfect to get around as well
our staying at zappa's place was great wish we could have stayed more
fantastic place to stay very quiet and close to restaurant and kayak adventures
great place and awesome experience would definitely come back
Read more reviews

7. Eco-friendly sailboat for adventurers

All aboard Mangrove Mango! This is an eco-friendly sailboat that’s ideal for the budget-conscious travelers. Mangrove Mango offers a “primitive camping” experience in Florida Keys. The sailboat is moored in shallow waters so you’ll need to take a kayak to reach this humble yet cozy camp in the waters. There are battery-powered fans to keep you cool on sweltering days, a small cooler, toiletries including organic shampoos and conditioners, bug spray, a solar shower, and life jackets. The kayak is also there for you and a friend to explore the beautiful network of passageways that meander through Key West’s mangrove forests.

Cozy 22 Foot Eco Sailboat w/Kayak (s)
Key West, Florida, United States
229 reviews
Boat 2 Beds 0 Bathrooms
Top guest reviews
Amenities & Room:
the bed is small but sufficient with the solar panel you can load your phones easily
the double bed was cozy but very comfortable
well thought out boat with all we needed for comfortable trip
everything was as expected - clean sheets plenty of batteries to operate fans and lanterns kayaks etc
we had an amazing time on zappa and amber's boat it was all very well organized and clean
zappa was a great host
the host is very warm and helpful
zappa is a fantastic host: friendly helpful caring kind and professional
great host who is very nice and easy to reach
hosts were very responsive and had great local tips
the location is beautiful and close to everything in key west
great location and easy commute to and from shore
great location super friendly hosts
we loved our stay there and their description of location and what to expect is spot on
great place to go for brocation* (brothers vacation trademark*)
Read more reviews

8. Homey sailboat with plenty of charm

Staying on a boat is a lot like camping, which is what most people who spend a lot of their time on boats will tell you. While sailing doesn’t always offer the most luxurious experience, you’ll enjoy it nonetheless, especially if you’re doing it while on vacation in Florida Keys! This homey sailboat isn’t the fanciest, but it can promise you a great night’s sleep with two cozy beds. Out in the marina, you can enjoy many activities and amenities the location has to offer: a pool, a restaurant and bar, and a laundry room and bathroom facilities. Don’t forget to come out at night while on the boat to soak in the nighttime view of the harbor. It’s definitely something to behold.

2/1 Free Kayak Free Shuttle 2 pools Dining on Site
Key West, Florida, United States
266 reviews
Boat 2 Beds 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
the bath/shower house was nice and having the hotel amenities was perfect
it was lovely to sit on the deck and watch the stars and was cozy and private
amazing to look up at night to see the stars from bed
the cabins tight but comfortable and serviceable
great place to stay with use of a lovely pool
bathhouse is clean and secure
the sail boat is clean and in a nice location
very clean and comfortable plus pj and stephanie are awesome
the space was clean and as well as the amenities
this boat was everything you could want in kw - clean convenient nice amenities
the hosts are very kind
pj is a great host
pj and stephanie were great hosts very friendly and helpful
the host was very responsive and the check-in was great
great place pj and stephanie were extremely responsive and flexible
excellent location with access to downtown
great location in a quiet marina
location for what we needed was perfect
very nice ship on nice location
best check-in ever beautiful boat amazing location
Read more reviews

9. Vintage 1964 Columbia sailboat for two

Sail around Florida Keys in this cozy, vintage 1964 Columbia sailboat. It’s the perfect crash pad on the high seas, with a sitting area, a bedroom for two, a separate living area, and ample counter space to prepare food. Not far from where you’ll dock are a grilling area and a freshwater station where you can stock up on all the essentials. Aboard, you’re free to use the towels and brew some coffee, or take out the complimentary kayak, snorkeling gear, or bicycle when you’re feeling adventurous.

Sailboat - Swim/Snorkel/Kayak
Islamorada, Florida, United States
675 reviews Superhost  Wifi Available
Boat 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
air conditioning kept the boat cool enough at night
the a/c kept us cool at night
the property was a perfect keys location with lounge chairs hammocks and picnic table
the bedding was clean and we woke up refreshed
the water right outside the door was so very warm clean and full of life
kevin is a very friendly host
friendly host well recommended
great area kevin was a wonderful host
kevin is very friendly and quick to answer questions
our hosts made our stay in the keys extra special
the location is amazing
beautiful location and pleasant stay
the location is beautiful and peaceful
excellent location with bikes to borrow for a ride down the bike path
this location is so beautiful you can't believe your eyes
Read more reviews

10. Sparkling 1977 sailboat with air-conditioning

Air-conditioning in sailboats is a luxury, so consider this Airbnb rental a treat! Docked in a marina village at downtown Key West, this 1977 Hunter sailboat has many things in store for you. There’s hot water to enjoy, a kitchen area where you can prepare and cook your fresh catch, and of course, a bathroom. This sailboat sleeps three, with one king bed and a single bed available. Out in the marina village, you’ll have access to a plethora of amenities, such as laundry, gym, and a swimming pool. You can also book private fishing and sailing charters here if you’re done being your own captain.

Hunter Cherubini Sailboat, “Seesea” 30 foot.
Key West, Florida, United States
463 reviews Superhost  Wifi Available
Boat 3 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
air conditioning worked great and tv was a bonus
the beds were super comfy and air conditioning kept us cool in the hot summer day
the sleeping quarters were comfortable
we truly enjoyed the cabin as it was very spacious and comfortable to sit read and simply relax
it was roomy and comfortable and is located in a great slip in the marina with awesome amenities
nice clean boat and nice marina with a pool
james’ boat was clean comfortable and cozy
a well kept vintage sailboat with clean decks easy access in a lovely location near key west
the place was nice and clean and had some cute amenities
jameson's boat is sparkling clean and gives an unforgettable experience of staying on the water
james was very responsive to our questions
he was very responsive to our questions
james is a great host very helpful and responsible
james was very responsive to our questions and helpful with suggestions
james is a wonderful host and very helpful when you have any questions or need help
location was good and the shuttle was an easy way to get to key west
beautiful place and great location very convenient to park the car and unpack our stuff
you will love this boat and location we did
definitely a great place to stay quite & fun location
there are places to eat within walking distance we had a great meal at the hogfish
Read more reviews

Bring out the inner sailor in you

Go kayaking, paddle-boarding, or snorkeling. Read your favorite book as you feel the wind in your hair. You can do all these and more when you explore the Florida Keys on your rented houseboat. Don’t forget to pack some coral-friendly SPF before you go!

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

Get Trip101 in your inbox

Unsubscribe in one click. See our privacy policy for more information on how we use your data

Born and raised in the Philippines, Vanna is 100% an island girl. During the weekdays, she works as a content editor for a US-based digital marketing firm. And when she isn't in front of her...Read more

 Want to contribute as a Local Expert?
Explore Florida Keys
Good things are meant to be shared!