Vacation rentals with a kayak in Florida Keys

Find and book unique kayak rentals on Airbnb

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Popular amenities for Florida Keys kayak rentals

House rentals with a kayak

Top guest favorite
Home in Key Largo
4.94 out of 5 average rating, 80 reviews

Large Waterfront Home, w/Efficiency, Pool, Kayaks

BrittanyRating, 5 stars1 month ago
We had everything we needed! Stu was helpful and responsive. We had a fantastic time and will be back in the future! Don’t miss a chance to stay here in Key Largo. Great location and loved keeping the boat behind the house. House is very clean and has all of the amenities you could possibly think of!! 10/10 recommend!
Top guest favorite
Home in Pompano Beach
4.96 out of 5 average rating, 23 reviews

Heated Pool! Waterfront+Pool Table! Close 2 Beach!

BrendanRating, 5 stars1 week ago
I had a wonderful stay! The house was clean and comfortable, and the pool was absolutely perfect for relaxing. The environment was peaceful and well-kept, making it a great place to unwind. Would definitely stay here again!
Superhost
Home in Naples
4.91 out of 5 average rating, 123 reviews

Best Value In Naples 4 Bdrm Pool Heat Walk Beach

ShawnRating, 5 stars2 days ago
This is our second year in a row staying at Bob’s home. We absolutely love the property. Close to the beach and lots of restaurants and many other things to do. The home is in great shape, very clean and all the amenities you need to enjoy the property! We will definitely book again.
Superhost
Home in Fort Lauderdale
4.92 out of 5 average rating, 124 reviews

Waterfront home walking distance to Las Olas/Beach

JocelynRating, 5 stars3 weeks ago
Great stay! The Airbnb was very clean, well-located, and an excellent value for the price. Would definitely recommend!
Superhost
Home in Cudjoe Key
4.83 out of 5 average rating, 263 reviews

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!

AngieRating, 5 stars2 weeks ago
Beautiful place with all the amenities and great location! We will be back!
Guest favorite
Home in Key Largo
4.83 out of 5 average rating, 60 reviews

Deckhouse

OkyoRating, 5 stars1 month ago
Absolutely amazing! Tanya’s Airbnb was the perfect venue for our wedding. The space was stunning, beautifully maintained, and created the most magical atmosphere for our special day. Tanya and Lana were incredible hosts—responsive, accommodating, and truly went above and beyond to make sure everything was perfect. Our guests couldn’t stop raving about the beautiful setting and how comfortable the stay was. If you’re looking for a dreamy location with a fantastic host, this is it! Highly recommend! Let me know if you’d like any tweaks!
Top guest favorite
Home in Naples
4.98 out of 5 average rating, 177 reviews

Gulf Access Sanctuary, Kayaks, Bikes, ebikes

MartinRating, 5 stars3 weeks ago
We had a very pleasant stay and would definitively book the house again.
Guest favorite
Home in Wilton Manors
4.93 out of 5 average rating, 55 reviews

River Access ~ Kayaks ~ Heated Pool

MoniqueRating, 5 stars1 month ago
Beautiful home, the interior was just like the photos, everything was sparkling clean too. The master bedroom was great and the bed was very comfortable. There was a little sharp area on the corner which needs some padding and duck tape. The backyard is perfect and the heated pool is quite relaxing. Unfortunately, the next door neighbors are doing heavy construction and it was so noisy and disruptive on Saturday. Also, the neighbors across the street in the multi-family were having major issues and altercations, I felt it was unsafe to walk the area. Even with the minor issues, we would stay again, we have family in the area and it’s so nice to visit. Thank you for the great stay, we had a blast! It was great to have pleasant weather too. We went to Rendez-Vous for brunch, The Alchemist for excellent Cappuccino’s, Las Olas blvd for walkable fun shopping, the Sandbar for lunch on the beach, J.Alexanders for dinner, Rosie’s for drinks, and Jets and Pepe’s for pizza,😊🫶👏🌈 incredible!

Cottage rentals with a kayak

Guest favorite
Cottage in Islamorada
4.96 out of 5 average rating, 79 reviews

Islamorada bungalow 2 bed & pool

KatieRating, 5 stars4 days ago
Beautifully decorated bungalow with everything you need for a relaxing holiday. We stayed with our two boys who loved the pool next door and the fire pit in the back garden. Great base for exploring Islamorada. Recommend watching the sunset and enjoying some great food at Papa Joes. Lovely responsive host
Top guest favorite
Cottage in Marathon
4.97 out of 5 average rating, 32 reviews

Catch n' Relax Canalfront Cottage in Marathon

SandyRating, 5 stars1 month ago
We stayed for 11 nights at Wendy's beautiful home. We had everything we needed for our entire stay. The area is very quiet and peaceful. It was so lovely walking up on the water and enjoying breakfast outside. Extra touches like having bikes and kayaks to use were also sooo nice! Wendy was very helpful with local spots to check out as well. We will definitely be back!
Guest favorite
Cottage in Naples
4.95 out of 5 average rating, 142 reviews

Tropical Cottage by the Sea- No Storm Damage

ScottRating, 5 stars2 weeks ago
Me and the doggies enjoyed our time at this location. Great restaurant at the top of the street and also enjoyed Celebration Square close by
Top guest favorite
Cottage in Key Largo
5 out of 5 average rating, 5 reviews

Kampground Paradise w/Kayaks, Heated Pool & Marina

TylerRating, 5 stars1 day ago
What an amazing stay!! The campground was so peaceful and tucked away from everyday reality. This trip was a much needed escape from our everyday life! The cottage was very new and clean and came with all the amenity’s needed to enjoy all the local beaches. The host was great and responded immediately with any questions we had. We will for sure be back again :)
Top guest favorite
Cottage in Naples
4.9 out of 5 average rating, 242 reviews

Cottage Close to Vanderbilt Beach Heated Pool

KendraRating, 5 stars1 month ago
We didn’t want to leave! Such a great house and location. It had everything we needed, including all kitchen ware. It was so nice being able to go up to Whole Foods & Trader Joe’s close by to cook at the house. The pool and screened in porch were so lovely. We’d definitely stay here again.
Guest favorite
Cottage in Cudjoe Key
4.93 out of 5 average rating, 121 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

TjRating, 5 stars3 weeks ago
What a fantastically beautiful place. right on the canals leading to the sea with spectacular views. Great hosts who were super responsive. Highly recommended
Top guest favorite
Cottage in Key Largo
5 out of 5 average rating, 12 reviews

New 150 ft Dock/Private Swim Spa/Tiki/Outdoor Bar

EdwardRating, 5 stars1 week ago
This was one of our favorite Air BnB rentals. The house was easy to get to from the Miami Airport, but was far away from the hustle of Florida. The amenities at the house were extraordinary and appropriate. Michelle was in the oversized hot tub twice a day while I was out on the canoe exploring the mangroves and fishing alongside Manatees and Stingrays. The dock provided multiple locations to be in, or out of the sun to fish, read or take in some sun. I did all three at the same time! The fire pit was in the perfect spot where we cooked most of our dinners. If you are looking for a spot for a mellow time to get away from the Northern cold and snow to relax, this is the spot. Sean was more accommodating and proactive with his replies and suggestions than most. There is even a sign on the refrigerator with his cell phone noting that 'if you are not having a 5* vacation, call me, and if you are, call me to rebook'! From the attention to detail throughout, he meant it!!
Guest favorite
Cottage in Key Largo
4.9 out of 5 average rating, 79 reviews

THE PARADISE

KariRating, 5 stars1 week ago
My husband and I stayed 3 nights and this place is so cute. Older tiny home with recent updates. Great location to be venture out and see Key Largo and it’s true .. the neighbors are so nice.

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