Top 10 Vacation Rentals In Florida Keys With A Boat - Updated 2022


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 in Florida Keys with a boat.

1. Tropical island getaway with private beach (from USD 1750)

This gorgeous home gives guests a private island experience right off the Florida Keys. 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.

Private Island, Offshore Florida Keys with sandy beach, gardens, boat & dock.
63 reviews  Wifi Available
resort 8 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 8
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

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

2. Spacious home with heated pool (from USD 279)

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.

Tiny house on the water. Pool, beach, dock, kayaks
Key Largo, Florida, United States
186 reviews  Wifi Available
Tiny home 4 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

3. Beautiful hideaway with gulf views (from USD 320)

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.

Middle Florida Keys Bayfront Hideaways with Sailboat, near Marathon and Key West
65 reviews  Wifi Available
cottage 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

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

4. Waterfront condo best for families (from USD 375)

This waterfront property is a great little home 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.

Waterfront Condo with Boat; Great for Families, Fishing, Diving and Cruising!
Key Largo, FL, US
6 Guests 2 Bedrooms 1 Bathroom

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

This waterfront home 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.

Paradise Place with Tiki Hut, Boats, Kayaks, Canoes, Paddleboard, 10 Bicycles
96 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

6. Bayfront vacation home with pool (from USD 485)

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.

Blue Vacation Home. Private heated pool.
97 reviews  Wifi Available
House 8 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 8
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

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

7. Cozy hideaway with heated pool (from USD 452)

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.

Tiny house2 on the water Pool, beach, dock, kayaks
47 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 711)

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. The villa is impeccably designed and furnished with modern appliances to make your stay as relaxing as possible.

144 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 249)

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.

57 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. Traditional-style cottage (from USD 310)

Located on Conch Key, this home can accommodate up to five people, making it an ideal spot for your next family vacation or romantic couples weekend away in the Florida Keys. The home is located midway between the mainland and the Florida Keys, making it ideal for sightseeing and boating on the water and still being relatively close to civilization. The island is sparsely developed, with only a few roads and homes, so you’ll feel like you’re on a tranquil tropical private island. The backyard area has everything from a tiki hut, where you can relax the night away, to hammocks for lounging in the sun and a grill for barbecuing in the evenings. The home is equipped with an optional motorboat for guests to cruise around in, but it is not for deep water fishing.

Kens Conch Key Cottage - Optional motor boat rental
61 reviews  Wifi Available
cottage 5 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 5
Minimum Nights: 5
Refund Policy :

Top guest reviews
Amenities & Room:
the internet and a/c are two of my main focuses and they were both excellent
i am sure he has fixed or replaced the water heater but be sure to ask about it
i felt comfortable leaving our fishing gear and other stuff outside the house without worry
the cottage was clean and just what we needed
we had a great time the cottage was clean and ready for us
well equipped cozy homely and characterfully decorated everything was very clean and worked well
ken was very accommodating and helpful
the owner was very forthcoming and helpful with my questions prior to and during our stay
ken was attentive to all our needs and very responsive
this home was comfortable and ken was really helpful with making suggestions before we checked in
we rode motorcycles and found the location to be great because it was centrally located in the keys
we loved the location and the tiki hut in the back that was right on the water
the location was perfect and the neighbors were nice
the area felt safe and we enjoyed walking around the neighborhood
enjoyed shopping in islamorada and feeding the tarpon at robbie’s
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.

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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