Top 11 Vacation Rentals With A Boat In Florida Keys - Updated 2024

Contributing Writer
| 5 min read

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 28, 2024.

1. Cozy rental offering two tandem kayaks and two paddle boards (from USD 295)

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.

Stayed at this property?
Key Largo, Florida, United States
10.5 km (6.6 mi) from John Pennekamp Coral Reef State Park
151 reviews   Superhost Wifi Available
Entire cottage 3 Beds 4 Guests 3 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the view of the canal from the living room just sets the vibe of tranquility
the bed was so comfortable and the small space is beautifully decorated
house was exceptionally clean and organized
the house is nice and clean
the house is clean new and comfortable
vivian had the place very clean upon arrival
great tiny house super clean and comfortable
wonderful host and beautiful property
the host was extremely helpful and always responded within minutes
vivian was super responsive to all my questions
our host vivian was very friendly and helpful and the place was in wonderful condition
she was clear and responsive from start to finish
very cute place near the water
a wonderful stay in a great location
the neighborhood is cute and quiet as well
the place was as neat as a pin and easy to social distance from others in the community
this was the ideal location for experiencing all that key largo has to offer
Read more reviews

2. The Glam Homes (from USD 1734)

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.

Stayed at this property?
Islamorada, Florida, United States
46.8 km (29.1 mi) from John Pennekamp Coral Reef State Park
49 reviews   Superhost Wifi Available
Entire villa 9 Beds 16 Guests 4 Bedrooms 4 Bathrooms

Accommodates: 16

Top guest reviews
and an excellent service and attention from the host
beautiful house in great location it has everything you need
the pool is the one perfect place to spend in the house after your time on the beach
Read more reviews

3. Tropical island getaway with private beach (from USD 1635)

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.

Stayed at this property?
Marathon, Florida, United States
81.18 km (50.5 mi) from John Pennekamp Coral Reef State Park
PRIVATE VACATION HOME 10 Guests 3 Bedrooms 3 Bathrooms

Top guest reviews
Amenities & Room:
it is definitely a room with a view
the wi-fi and phone signal worked perfectly so i was still able to work
not having a/c in the house actually pushed us to enjoy the outdoors to the max
everybody was so helpful and let us enjoy this awesome week with our boys even more
it's clear that the owners love this place because it is so well thought out and cared for
we wish that everyone could see and experience such a great place
we looked for a special place to bring our family for a rare weeklong get-together and we found it
Read more reviews

4. Spacious home with heated pool (from USD 249)

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.

Stayed at this property?
Key Largo, Florida, United States
6.21 km (3.9 mi) from John Pennekamp Coral Reef State Park
260 reviews   Wifi Available
Tiny home 3 Beds 6 Guests 2 Bedrooms 1 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
comfortable beds nice linens
the bed was comfortable shower was good and the kitchen facilities (oven and fridge/freezer) were outstanding
very clean and nice place
nice tiny house very clean and stylish
the tiny house was clean and very modern
clean and compact but very efficient and thoughtfully decorated
great space adorable comfortable sparkling clean tiny home
highly recommend this property and host
having the amenity of the kayak's and paddleboards was amazing great home and host
host gave us great recommendations about things to do and places to eat in the area
great location amazing outdoor location
outstanding location and excellent accommodation
supermarket within walking distance is also great
location and price were great
amazing location next to kayaking trails and state park
Read more reviews

5. Waterfront condo best for families (from USD 380)

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.

Stayed at this property?
Key Largo, Florida, United States
4.1 km (2.6 mi) from John Pennekamp Coral Reef State Park
condo 6 Guests 2 Bedrooms 1 Bathroom

Top guest reviews
the condo was clean and stocked as described
the condo was comfortable and clean and the boat was fun
jay was helpful at check in
the condo was comfortable and close to everything
the location in the canal was wonderful and it was nice and quiet
Read more reviews

6. Spacious accommodation with dock and tiki hut (from USD 250)

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.

Stayed at this property?

1.3 km (0.9 mi) from John Pennekamp Coral Reef State Park
98 reviews   Wifi Available
House 10 Guests 4 Bedrooms 5 Bathrooms

Accommodates: 10
Minimum Nights: 28
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
good wifi cable tv full kitchen
loved the deck and the outside shower
really appreciated the fans and stereo
the house itself is wonderfully stocked and had enough room for our entire family
with the tv it was nice to sit out and watch our favorite shows
the house was impeccably clean and beautifully decorated
the beds were comfortable and clean and bathrooms fine
the beds were comfortable and clean
everything was clean and ready to go
the house is comfortable and clean
jim the property owner is amazing and so kind
jim was the best possible host taking care of us without a complaint
he was extra helpful and took care of our needs before we even asked
jim is great and very accommodating
what an amazing property owner
the location couldn’t be better
the yard and location were wonderful close to everything
neighbors are great and the location is perfect
the location of this rental is great too
good restaurants bait shops and grocery stores nearby but car is recommended
Read more reviews

7. Cozy hideaway with heated pool (from USD 357)

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.

Stayed at this property?

6.29 km (4.0 mi) from John Pennekamp Coral Reef State Park
55 reviews   Wifi Available
House 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
clean and wonderful to stay in
it was bright clean and well equipped
this house is very clean and looks newly renovated
tiny house is very clean and well taken care of
the house is super clean and the water is really six steps from the door
location location location and beautiful
the location of this property is the best in the park
loved our stay great location and loved the kayaks
Read more reviews

8. Upscale villa with access to pools (from USD 491)

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.

Stayed at this property?

10.91 km (6.8 mi) from John Pennekamp Coral Reef State Park
155 reviews   Wifi Available
townhome 8 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 8
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
owner was responsive to issue we had with tv connection
everything was clean comfortable and nice
very clean and grounds very well kept
place was very clean and perfect for our family
the lagoon outside property although dark looking was clean and husband and son both swam there quite happily
the property manager was very helpful and responsive
the owner was very responsive helpful and accommodating
property was good communication with owner was easy
nice location easy to access main hwy
very nice area close to everything great for kids
good dining options in the immediate area- walkable to the pilot house & fisheries
good places to eat nearby
Read more reviews

9. Pet-friendly lodge with panoramic ocean views (from USD 259)

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 pet-friendly 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.

Stayed at this property?

80.55 km (50.1 mi) from John Pennekamp Coral Reef State Park
65 reviews   Wifi Available
House 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
screened porch overlooking the water was perfect for drinking coffee/eating breakfast in the morning
we appreciated the comfortable beds plush towels and all the amenities provided
comfortable space for two couples
nice and clean well stocked
the house was clean and bright
it was clean and comfy and met all our needs
very clean and equipped house everything you need
property was open and clean well decorated with all basic needs
the owner is very pleasant and quick to respond
the home was great location is perfect and owner was very helpful and responsive
the owner melissa was attentive and helpful with any questions we had recommendations in the area etc
bob is friendly and easy to work with and easy to get ahold of
convenient location within easy biking distance to the cabana club
marathon is a great location
beautiful location right on the water
very nice and relaxing location
great location and a well kept property
Read more reviews

10. Beautiful hideaway with gulf views (from USD 299)

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.

Stayed at this property?
marathon, Florida, United States
66.04 km (41.1 mi) from John Pennekamp Coral Reef State Park
cottage 6 Guests 2 Bedrooms 1 Bathroom

Top guest reviews
Amenities & Room:
we had 6 adults and two slept comfortably in the living room on an air mattress
if you like cozy and charming this 2 bedroom cottage is for you
this is what we particularly liked all very clean comfortable beds good efficient air con and ceiling fans
it was clean charming and offered everything we could need and more
everything was well stocked and super clean
bathrooms are stocked and clean
they offer a great clean cottage with a great view
clean well appointed kitchen icy cold a/c comfy beds and pillows
tom and peggy were friendly hosts and made you feel at home
tom was very friendly and went out of his way to make your stay as pleasant as possible
barry and tammy are great hosts
what a great place and wonderful hosts
wonderful hosts just as are capt
perfect location to enjoy many areas of the keys
a place to sail to where we all wish to be
we could have easily spent a couple more days at this location
the house is in a perfect central location for snorkeling fishing or heading south to key west
the sailing kayaking snorkeling swimming hiking bike rides and daily walks were great
Read more reviews

11. Bayfront vacation home with pool (from USD 403)

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.

Stayed at this property?
Cudjoe Key, Florida, United States
125.9 km (78.3 mi) from John Pennekamp Coral Reef State Park
PRIVATE VACATION HOME 8 Guests 4 Bedrooms 2 Bathrooms

Top guest reviews
Amenities & Room:
we especially liked the pool and outside space on the deck and at the water front
one of the best amenities is that you have your own private pool
the pool is fantastic it is heated so we were able to use at any time
we had no issues with the house loved it and very clean and useable
beach house was so nice very clean and exceeded our expectations
the home was beautiful clean and just perfect for us
house was clean and is somewhat spacious and accommodated all seven of us well
their first time in the florida keys house very clean pics of this property don’t do it justice
the owner was very responsive to our requests
mitch is a great host
the owner was very nice and always available if we needed anything
great property and a super helpful host (mitch)
mitch and zack were very responsive and accommodating to any questions we had
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&r
this is a great location for a base on visiting key west
location is great for access to activities and key west
everything about this property was so great location amenities communication with owner easy check in
Read more reviews

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

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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Alex is a Canadian university graduate with degrees in English literature and History. He was born in Montreal and when he's not traveling he enjoys movies, video games, playing the drums and...Read more

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