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 stars2 weeks 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 stars6 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 stars4 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 stars3 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, 178 reviews

Gulf Access Sanctuary, Kayaks, Bikes, ebikes

TagRating, 5 stars1 week ago
Be open on your expectations and Jody is very accommodative. The Spa/massage recommendation was spot on and amazing. The home was excellent and met all expectations for our family.
Top guest favorite
Home in Marathon
4.98 out of 5 average rating, 49 reviews

Waterfront Heated Pool 120 ft Boat Dock

JulieRating, 5 stars4 weeks ago
We had a wonderful stay at Miltons house. We were greeted by a beautiful bottle of wine, thank you very much! The house was amazing, spacious, super-super clean, with a gorgeous kitchen and bathrooms. House was very well stocked with anything you need and beautifully decorated. Huge TV in the living room with access to your Amazon, Netflix accounts with a super fast internet service. Washers and dryers were so convenient for an extended stay. We spent one week enjoying the pool, fishing from the dock and kayaking. Fishing was good, my husband caught two Grunts, a Silver Jenny, a Pin Fish and a Baracuda. He had a wonderful time. The pool was beautiful and made our stay more special. It was nice floating in the pool and watching pelicans on the canal. Neighborhood was very peaceful. On our first day we saw a manatee right from the dock, it was an unexpected surprise. Thank you very much Milton for the opportunity to enjoy your lovely home! It completely exceeded our expectations which w

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 stars1 week 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, 143 reviews

Tropical Cottage by the Sea- No Storm Damage

LaurenRating, 5 stars3 days ago
The place itself was so beautiful and the outdoor space leading right to the lake was so peaceful! I enjoyed sitting on the porch in the mornings for a quiet, relaxing start to the day! Robin was very friendly and provided helpful instructions. Definitely recommend 😊
Top guest favorite
Cottage in Key Largo
5 out of 5 average rating, 6 reviews

Kampground Paradise w/Kayaks, Heated Pool & Marina

TylerRating, 5 stars5 days 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 stars4 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 stars2 weeks 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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