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, 82 reviews

Large Waterfront Home, w/Efficiency, Pool, Kayaks

RogerRating, 5 stars2 weeks ago
We had an absolutely wonderful stay here! It couldn’t have been any better. The house is laid out in a perfect way inside and out to make you just relax and enjoy the relaxed Key Largo way of life! There is an abundance of lovely towels for the bathroom as well as the pool, all showers are stocked with shower gels and soaps – it feels like a 5 star hotel! We appreciated all the personal touches very much. We love wildlife and we saw Manatees swim past us a few times, ospreys around us and such beautiful bird song. The layout allows you to enjoy the day downstairs on the deck in sun surrounded by palm trees and shade on the lovely outdoor seating area whatever you wish and the BBQ facility allows you to cook and enjoy the outdoor life. Upstairs has a great balcony place to sit outside at night around the table and enjoy dinner fully enclosed with mosquito netting so that you don’t get targeted or bitten. We loved our kayaking around the Mangroves and all the wildlife you can see
Top guest favorite
Home in Pompano Beach
4.96 out of 5 average rating, 24 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 stars1 week 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.
Guest favorite
Home in Fort Lauderdale
4.92 out of 5 average rating, 124 reviews

Waterfront home walking distance to Las Olas/Beach

JocelynRating, 5 stars1 month 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 stars4 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 stars2 weeks 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, 50 reviews

Waterfront Heated Pool 120 ft Boat Dock

ColmRating, 5 stars1 week ago
Really nice house - it’s bigger than it looks in the photos, was really clean and it had everything we needed. Perfect place to relax and a great base to explore the Keys. Easy access to a bay for safe kayaking or if you have smaller kids they can kayak in the canal by the house. It is in a really quiet residential neighbourhood and just a short drive to all amenities. Host was exceptionally responsive.

Cottage rentals with a kayak

Top guest favorite
Cottage in Bonita Springs
4.98 out of 5 average rating, 59 reviews

The Enchanted Cottage on the Imperial River

Mary AnnRating, 5 stars1 week ago
We had an amazing stay at this beautiful property! It was exactly as described in the listing—immaculate, relaxing, and truly inviting. The attention to detail in the design and decor made it a joy to spend time there. It was clear that a lot of thought had gone into making the space both comfortable and aesthetically pleasing. Mona was an outstanding host—friendly, helpful, and always quick to respond to any questions we had. She even sent us a heads-up (and picture) about an alligator who was in the area to make sure our fur-babies were safe. She made the entire process seamless and stress-free, which we greatly appreciated. If you're looking for a stunning property with a host who genuinely cares about your experience, this is the place to book. Highly recommended!
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 stars1 week 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 stars1 week 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, 122 reviews

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

ElisaRating, 5 stars2 weeks ago
Cute spot! There’s a small store nearby if you didn’t bring soap or shampoo. Pools are heated and close by. Beautiful beaches 30 minutes away by car and Duval st if you’re into nightlife. Was very quiet area so if you have loud kids like we did then reconsider haha but overall we had a great time!
Top guest favorite
Cottage in Key Largo
5 out of 5 average rating, 13 reviews

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

EdwardRating, 5 stars3 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, 81 reviews

THE PARADISE

LeahRating, 5 stars6 days ago
We enjoyed our stay! Nice location, right on the water. We were able to jump right in the kayaks and get out to spend the day on the water. House was just as described and had everything we needed for a weekend getaway. Host was great and very responsive! Thank you.

Cabin rentals with a kayak

Superhost
Cabin in Bonita Springs
4.78 out of 5 average rating, 268 reviews

Exotic, Romantic, Private River Cabin for 2

MichaelRating, 5 stars2 weeks ago
Thanks for the great place to stay!
Guest favorite
Cabin in Bonita Springs
4.9 out of 5 average rating, 278 reviews

Romantic River Cabin for 2; Beautiful Nature View

OdileRating, 5 stars3 weeks ago
We enjoyed the house. Very comfortable and clean. The screened porch was perfect for the morning coffee! There was some beach equipment and kayaks. Very useful. The river was perfect for kayaking. Would stay there again!
Superhost
Private room in Marathon
4.68 out of 5 average rating, 19 reviews

Viamarhe Cabin-Private beach, Kayak, yard games

RachelRating, 5 stars3 months ago
We spent a week here and loved it, it was the perfect size for me and my husband to celebrate our anniversary. It was clean and spotless. We loved to sit out by the water and watch the wildlife, jet skis and wind surfers. It's so peaceful around there. There are also lots of great restaurants near by. We hope to come back again sometime.
Guest favorite
Cabin in Key West
4.87 out of 5 average rating, 15 reviews

Living life Dockside

AndrewRating, 5 stars1 month ago
Everything and everybody far exceeded any expectations. We have already started planning our next stay. This was easily one of the best experiences I have ever had with any rental service.
Cabin in Marathon
4.85 out of 5 average rating, 121 reviews

New Waterfront Cabins at Bonefish Bay

ShailRating, 5 stars5 days ago
Lisa's place was super centrally located in Marathon - it was a great base for us to explore the Florida Keys for the first time. The wooden cabins are mobile units but they're extremely well designed and planned such that it never felt tight in the cozy amount of space for me, my wife and toddler. The onsite amenities such as pickleball court, bikes available for use and kayaks were all great bonus provisions that made the stay fun. Highly recommend!

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