The state of Florida is one of the biggest vacation destinations in the United States. The area draws tourists from all over country as well as abroad. Florida is the country’s tropical vacation destination and the Florida Keys is the area where you’ll want to be. For people into boating, fishing, and enjoying day cruises, there is no better place than the Florida Keys. There’s a reason Hemingway lived and fished here, and if you’re a boating enthusiast, you’ll understand why too. You can also hang out on beaches, and spend tons of time outdoors in Florida Keys. Check out these top vacation rentals with a boat in Florida Keys.
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 June 29, 2025.
1. Tropical island getaway with private beach (from USD 1771)
This gorgeous vacation rental with a boat dock in the Florida Keys gives guests a private island experience. Sleeping up to eight people, this tropical home is only accessible by boat. Once guests arrive, they will be greeted by the manager who will show you around. The is fully equipped with a kitchen, three bedrooms, and three bathrooms, and after your tour of the home, you’re ready to begin your tropical vacation. The home is equipped with two kayaks as well as a 19-foot (5.7 meters) boat for your personal enjoyment.
Guests will also have personal beach access as well as access to modern luxury amenities like laundry facilities and WiFi. Lounge on the wrap-around deck and stare out onto the ocean or wake up in the mornings with a fresh cup of coffee and breath in the salty ocean air. This Florida Keys rental with a boat included is eco-friendly and was designed to be sustainable to the environment surrounding it.
Top guest reviews
Host:
everybody was so helpful and let us enjoy this awesome week with our boys even moreit's clear that the owners love this place because it is so well thought out and cared forLocation:
we wish that everyone could see and experience such a great placewe looked for a special place to bring our family for a rare weeklong get-together and we found itRead more reviewsAmenities & Room:
it is definitely a room with a viewthe wi-fi and phone signal worked perfectly so i was still able to worknot having a/c in the house actually pushed us to enjoy the outdoors to the max
2. Spacious home with heated pool (from USD 408)
This Airbnb vacation rental with a boat included in Florida Keys is located in a small community and comes with some great amenities, like a boat for your private use and even beach access. Sleeping up to six people, the home is brand new and equipped with a modern kitchen, utensils, and cookware as well as linens and towels. There is a full bathroom with a shower and plenty of other great little bonus amenities for your stay like laundry services, a heated swimming pool, WiFi access, and a basketball court.
Top guest reviews
Host:
highly recommend this property and hosthaving the amenity of the kayak's and paddleboards was amazing great home and hosthost gave us great recommendations about things to do and places to eat in the areaLocation:
great location amazing outdoor locationoutstanding location and excellent accommodationsupermarket within walking distance is also greatlocation and price were greatamazing location next to kayaking trails and state parkCleanliness:
very clean and nice placenice tiny house very clean and stylishthe tiny house was clean and very modernclean and compact but very efficient and thoughtfully decoratedgreat space adorable comfortable sparkling clean tiny homeRead more reviewsAmenities & Room:
comfortable beds nice linensthe bed was comfortable shower was good and the kitchen facilities (oven and fridge/freezer) were outstanding
3. Waterfront condo best for families (from USD 441)
This waterfront vacation home in the Florida Keys is a great little accommodation that sleeps up to six people, making it a great little spot for your next family vacation. Relax in the privacy of this waterfront condo and wake up every morning to the soothing sounds of water and the fresh ocean air. The home has a gorgeous screened-in porch that guests can relax on in the evenings without being bothered by bugs and you’ll find a full kitchen and linens included, as well. If you’re looking to head out onto the water, there is a 23-foot (7 meters) Mako boat equipped with GPS and safety equipment.
Top guest reviews
Host:
jay was helpful at check inLocation:
the condo was comfortable and close to everythingthe location in the canal was wonderful and it was nice and quietRead more reviewsCleanliness:
the condo was clean and stocked as describedthe condo was comfortable and clean and the boat was fun
4. Beautiful hideaway with gulf views (from USD 298)
Located on a small island called “Conch Key”, this little home is tucked away on the side of the island, where you’ll feel like you’re on your own private tropical paradise. The home can sleep up to six people and quite possibly offers some of the best views of the Gulf. With near endless 360-degree views of the water from the house, guests will also have access to a 23-foot (7 meter) long boat they can take out onto the water and do some fishing or simply explore the surrounding area. This Florida Keys vacation rental with boat is child-friendly and also offers TV access with satellite and WiFi access, as well.
Top guest reviews
Host:
tom and peggy were friendly hosts and made you feel at hometom was very friendly and went out of his way to make your stay as pleasant as possiblebarry and tammy are great hostswhat a great place and wonderful hostswonderful hosts just as are captLocation:
perfect location to enjoy many areas of the keysa place to sail to where we all wish to bewe could have easily spent a couple more days at this locationthe house is in a perfect central location for snorkeling fishing or heading south to key westthe sailing kayaking snorkeling swimming hiking bike rides and daily walks were greatCleanliness:
it was clean charming and offered everything we could need and moreeverything was well stocked and super cleanbathrooms are stocked and cleanthey offer a great clean cottage with a great viewclean well appointed kitchen icy cold a/c comfy beds and pillowsRead more reviewsAmenities & Room:
we had 6 adults and two slept comfortably in the living room on an air mattressif you like cozy and charming this 2 bedroom cottage is for youthis is what we particularly liked all very clean comfortable beds good efficient air con and ceiling fans
5. Spacious accommodation with dock and tiki hut (from USD 287)
This waterfront house rental with a boat in the Florida Keys has everything you need to ensure a memorable Key Largo escapade. It’s right by the water, surrounded by lush tropical plants, providing you with serene views wherever you look. You will also have access to a private dock equipped with a boat, kayak, canoe, paddleboard, and other equipment, allowing you to fully explore the waters however you like. This Florida Keys house rental with a boat can also sleep up to ten, perfect for large groups.
Top guest reviews
Host:
jim the property owner is amazing and so kindjim was the best possible host taking care of us without a complainthe was extra helpful and took care of our needs before we even askedjim is great and very accommodatingwhat an amazing property ownerLocation:
the location couldn’t be betterthe yard and location were wonderful close to everythingneighbors are great and the location is perfectthe location of this rental is great toogood restaurants bait shops and grocery stores nearby but car is recommendedCleanliness:
the house was impeccably clean and beautifully decoratedthe beds were comfortable and clean and bathrooms finethe beds were comfortable and cleaneverything was clean and ready to gothe house is comfortable and cleanRead more reviewsAmenities & Room:
good wifi cable tv full kitchenloved the deck and the outside showerreally appreciated the fans and stereothe house itself is wonderfully stocked and had enough room for our entire familywith the tv it was nice to sit out and watch our favorite shows
6. Cozy hideaway with heated pool (from USD 318)
Make the most of your Key Largo adventure in this charming tiny home. Located in a nice waterfront community, this Florida Keys rental with boat is the perfect launch off point to experience what this vacation hotspot has to offer—from deep-sea fishing to scuba diving. Guests will have access to the kids’ playground and heated pool. There’s also a large wooden deck that faces the water where you can chill out while enjoying the natural beauty surrounding you.
Top guest reviews
Location:
location location location and beautifulthe location of this property is the best in the parkloved our stay great location and loved the kayaksRead more reviewsCleanliness:
clean and wonderful to stay init was bright clean and well equippedthis house is very clean and looks newly renovatedtiny house is very clean and well taken care ofthe house is super clean and the water is really six steps from the door
7. Upscale villa with access to pools (from USD 452)
This luxurious villa is centrally located, making it a perfect home base for those who want to experience everything Key Largo has to offer. Guests have quick and easy access to the water and enjoy many fun recreational activities, including boating, kayaking, fishing, paddle boarding, scuba diving, or just taking in the beautiful sights under the sun. This vacation rental with a boat included in Florida is impeccably designed and furnished with modern appliances to make your stay as relaxing as possible.
Top guest reviews
Host:
the property manager was very helpful and responsivethe owner was very responsive helpful and accommodatingproperty was good communication with owner was easyLocation:
nice location easy to access main hwyvery nice area close to everything great for kidsgood dining options in the immediate area- walkable to the pilot house & fisheriesgood places to eat nearbyCleanliness:
everything was clean comfortable and nicevery clean and grounds very well keptplace was very clean and perfect for our familythe lagoon outside property although dark looking was clean and husband and son both swam there quite happilyRead more reviewsAmenities & Room:
owner was responsive to issue we had with tv connection
8. Pet-friendly lodge with panoramic ocean views (from USD 311)
Fun water activities are literally just a few steps away from this cozy waterfront vacation rental. The dozens of recreational activities such as kayaking, fishing, and more are right at your doorstep and complimented with panoramic views of the open waters from the front and back.
This vacation rental also features ample room to accommodate up to four persons plus pets (with prior approval), perfect for mid-sized groups on a Key Largo adventure. Wi-Fi, cable TV, full kitchen, and other modern amenities ensure comfort and convenience.
Top guest reviews
Host:
the owner is very pleasant and quick to respondthe home was great location is perfect and owner was very helpful and responsivethe owner melissa was attentive and helpful with any questions we had recommendations in the area etcbob is friendly and easy to work with and easy to get ahold ofLocation:
convenient location within easy biking distance to the cabana clubmarathon is a great locationbeautiful location right on the watervery nice and relaxing locationgreat location and a well kept propertyCleanliness:
nice and clean well stockedthe house was clean and brightit was clean and comfy and met all our needsvery clean and equipped house everything you needproperty was open and clean well decorated with all basic needsRead more reviewsAmenities & Room:
screened porch overlooking the water was perfect for drinking coffee/eating breakfast in the morningwe appreciated the comfortable beds plush towels and all the amenities providedcomfortable space for two couples
9. Bayfront vacation home with pool (from USD 537)
Perfect for friends or families, this vacation home can sleep up to eight. The house is fully equipped with modern amenities like Internet connection, air conditioning, cable TV, microwave, fridge, and more to ensure comfort and convenience. Use the kayak, rent the pontoon, or rent a boat and catch popular fish like snappers, wahoos, and more in the abundant Cudjoe Bay. After a fun day of fishing, you can relax by the pool as you grill the day’s catch.
Top guest reviews
Host:
the owner was very responsive to our requestsmitch is a great hostthe owner was very nice and always available if we needed anythinggreat property and a super helpful host (mitch)mitch and zack were very responsive and accommodating to any questions we hadLocation:
nicely located on cudjoe key close to key west and to big pine key& a convenience store is a short walk away near property) cudjoe key is great for r&rthis is a great location for a base on visiting key westlocation is great for access to activities and key westeverything about this property was so great location amenities communication with owner easy check inCleanliness:
we had no issues with the house loved it and very clean and useablebeach house was so nice very clean and exceeded our expectationsthe home was beautiful clean and just perfect for ushouse was clean and is somewhat spacious and accommodated all seven of us welltheir first time in the florida keys house very clean pics of this property don’t do it justiceRead more reviewsAmenities & Room:
we especially liked the pool and outside space on the deck and at the water frontone of the best amenities is that you have your own private poolthe pool is fantastic it is heated so we were able to use at any time
10. Cozy rental offering two tandem kayaks and two paddle boards (from USD 1523)
With three beautifully appointed bedrooms - two with queen-sized beds and one with a single bed - you’ll find ample space for up to five guests. This cozy retreat comes fully equipped with a well-appointed kitchen featuring an Instapot, coffee maker, and more. The amenities extend beyond, including Wi-Fi, cable TV, and air conditioning to keep you connected and comfortable. Laundry facilities with a washing machine and dryer ensure convenience during your stay. Well-behaved pets are welcome with prior approval.
Step outside to a private patio or balcony where you can soak in the serene surroundings. But that’s not all – this rental includes two tandem kayaks and two paddle boards, perfect for exploring the nearby waterways. There’s even a shared pool for relaxation. Boating enthusiasts will appreciate the opportunity to dock their vessels, and there’s a community boat ramp nearby for easy access.
Top guest reviews
Host:
wonderful host and beautiful propertythe host was extremely helpful and always responded within minutesvivian was super responsive to all my questionsour host vivian was very friendly and helpful and the place was in wonderful conditionshe was clear and responsive from start to finishLocation:
very cute place near the watera wonderful stay in a great locationthe neighborhood is cute and quiet as wellthe place was as neat as a pin and easy to social distance from others in the communitythis was the ideal location for experiencing all that key largo has to offerCleanliness:
house was exceptionally clean and organizedthe house is nice and cleanthe house is clean new and comfortablevivian had the place very clean upon arrivalgreat tiny house super clean and comfortableRead more reviewsAmenities & Room:
the view of the canal from the living room just sets the vibe of tranquilitythe bed was so comfortable and the small space is beautifully decorated
11. The Glam Homes (from USD 1227)
Indulge in the ultimate beachfront escape at this splendid villa, catering to groups of all sizes. This four-bedroom accommodation features a sumptuous king-size bed with a private balcony offering awe-inspiring sea vistas, four queen-size beds, and two double beds. Throughout the villa, cherry hardwood flooring adds an elegant touch, complementing the fully equipped kitchen with granite countertops and stainless appliances, including a gas stove.
For your security, discreetly placed cameras monitor the property. While kayaks and paddle boards are available for rent through their partnered Keys rental service, pets are also welcome for a fee of $300 per pet.
Top guest reviews
Host:
and an excellent service and attention from the hostRead more reviewsLocation:
beautiful house in great location it has everything you needthe pool is the one perfect place to spend in the house after your time on the beach
Cruising through Florida Keys
With its all-inclusive resorts and luxury hotels, Florida Keys is one of the best spots in the state for vacation. If you’re looking for a tropical getaway destination this year, consider heading to one of these great houses on the water. Complete with your own private boat and dock, you’ll quickly learn why Florida Keys is such a popular destination.
Frequently asked questions about vacation rentals with a boat in Florida Keys
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