
Holiday rentals with a kayak in Florida Keys
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Florida Keys
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for kayak rentals in Florida Keys
House rentals with a kayak

Paradise found!Key Colony Beach,Cabana Club.
We had a great week at Kari's place. We were blown away by the view from the terrace. The apartment was well appointed and had everything we needed. The use of the nearby Cabana club was a real bonus. Colony Key is about an hour from Key West, so it was well located for all sorts of activities. Would love to return one day. Thanks Kari. Colin & Lynne Moore. Buckinghamshire, UK

Dock Pool Ramp Jacuzzi Ocean Views Kayaks
This stay was the perfect vacation I was looking forward to, I stayed 7 days at this water front property with a great balcony to enjoy evenings and a boat ramp to launch the boats in the back yard along with the pool to keep us cool. Plenty of room for our trucks and trailers, the inside of the home was comfortable and relaxing. Was truly a great vacation Thank you

Million Dollar View
This home was everything we expected and more. Stunning location with absolute privacy. The extra long dock was amazing, the pool was fantastic, and the grounds were meticulous. It’s literally your own private resort. Roman, the host, was very quick with communication. He and his wife actually met us when we checked in to see if we had any questions and provided us with an arrival gift. If you have looked at the listing and are thinking of renting it, do it. You will not be disappointed at all. Excellent value all around.

Key Largo Waterfront Home with Tiki & Boat Dock
We have found our home away from home when we visit the Keys! Penny’s house was not only exactly as described, but something about it just felt like home. We came home and immediately booked another stay. Penny was responsive, friendly and we enjoyed sending her pictures from our stay. Our daughter is 4 and learned how to fish during our stay - The core memories were endless! We enjoyed daily manatee visits, so much fishing, and visiting local restaurants! Princess the sweet community kitty has a special place in our heart, please feed her during your stay :)

Lighthouse - Beach Houses Key West
We loved our stay at The Lighthouse! The place was clean, host was responsive, pool area was great, and the ocean was beautiful. While we were in heavy seaweed time, we enjoyed coffee on the deck every morning with beautiful sunrises and water scenes. The pool and BBQ area was amazing!! We grilled almost every night there and had all we needed. We enjoyed having bikes to ride the island! 10/10 stay and we will definitely be back!

Viamarhe House-Private beach, Kayak, yard games
Loved our week-long stay at Marjorie’s! As pictured and described. Checked out the other reviews for useful tips.

New Oceanside Casa Azul! Voted #1! Golf Cart-Beach
Martha was super helpful and responsive. The place was very nice, clean, and had incredible amenities. Kids loved it!

July 4 Deal! Serenity Oasis~Kayaks~Bikes!~HotTub!
The house was fantastic! Every nook was well thought out, utilized, decorated and delivered beautifully. The kitchen is well appointed, the baths were gorgeous, the deck was quiet and one of our favorite spaces. Well done, we will miss Serenity Oasis!
Cottage rentals with a kayak

Cozy Tropical Cottage. Your new Happy Place!
Toni's place was exactly what my partner and I needed for our trip to Florida for a family memorial, and Toni herself was *extremely* helpful and communicative! The home itself was perfect, the amenities provided were fantastic, the walkability of the neighborhood was amazing, and the lovely outdoor area made me wish I could have orchids growing on trees in Illinois (there's also a GIANT staghorn fern ball hanging outside the back door - my jaw dropped when I saw it). Highly recommend the Riverside Market a few minutes walk from the home (make sure to try the fried chickpeas!) and the pizza spot across the street from there :)

Islamorada bungalow 2 bed & pool
The hosts were very responsive and accommodating to our needs. The pool was great and the place was pristine!

Ocean Breeze at Venture Out 537
I had a wonderful stay at this Airbnb! The home was perfect for our occasion—just as advertised, and even more charming in person. The vibrant and inviting colors gave the space a warm, welcoming feel. There was a slight delay with check-in, but our host, John, responded quickly and resolved the issue right away, which we really appreciated. We also took full advantage of the amenities, which added to the overall experience. Everything was clean, comfortable, and well thought out. I would definitely stay here again and highly recommend it to others!

Catch n' Relax Canalfront Cottage in Marathon
We really enjoyed our stay at Wendy's place! It was clean, comfortable, and had everything we needed for our stay. We enjoyed riding the bikes to Seven Mile Bridge and exploring with the kayaks. Would definitely recommend it!

Oceanfront Getaway | Kayaks, BBQ & Stunning View!
Enjoyed the stay. Was very well equipped with everything we needed. We had a question about one of the keys and host was very responsive.

Tropical Cottage by the Sea- No Storm Damage
This was an amazing place! Perfectly located and the views were breathtaking. Great place to unwind, relax and go on adventures! Very clean and felt just like home!

Cottage Close to Vanderbilt Beach Heated Pool
Great house in a nice quiet neighborhood close to the beach. House was exactly as the photos. Nice pool and backyard and covered lanai. Mercato less than a mile away, with great shopping and restaurants.

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
We brought another couple with us. Had a relaxing enjoyable time. Felt like home. Definitely be back. Thank you
Destinations to explore
- Miami Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Key West Holiday rentals
- Havana Holiday rentals
- Central Florida Holiday rentals
- Tampa Bay Holiday rentals
- Kissimmee Holiday rentals
- St Petersburg Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Family-friendly rentals Florida Keys
- Guest house rentals Florida Keys
- Mansion rentals Florida Keys
- Rentals with a cinema Florida Keys
- Townhouse rentals Florida Keys
- Rentals with a hot tub Florida Keys
- Flat rentals Florida Keys
- Rentals with lake access Florida Keys
- Beach apartment rentals Florida Keys
- Campsite rentals Florida Keys
- Motorhome rentals Florida Keys
- Rentals with a sauna Florida Keys
- Apartment rentals Florida Keys
- Fitness-friendly rentals Florida Keys
- Beach house rentals Florida Keys
- Cottage rentals Florida Keys
- Tiny house rentals Florida Keys
- Private suite rentals Florida Keys
- Waterfront rentals Florida Keys
- Luxury rentals Florida Keys
- Rentals with a washing machine and dryer Florida Keys
- Bed and breakfasts Florida Keys
- Rentals with breakfast Florida Keys
- Serviced apartment rentals Florida Keys
- Villa rentals Florida Keys
- Rentals with an accessible-height toilet Florida Keys
- Rentals with an accessible-height bed Florida Keys
- Rentals with beach access Florida Keys
- Pet-friendly rentals Florida Keys
- Smoking-friendly rentals Florida Keys
- Ski-in/ski-out rentals Florida Keys
- Rentals with a firepit Florida Keys
- Hotel rentals Florida Keys
- Family-friendly rentals Florida Keys
- House rentals Florida Keys
- Beachfront rentals Florida Keys
- Rentals with a patio Florida Keys
- Rentals with a fireplace Florida Keys
- Bungalow rentals Florida Keys
- Rentals with outdoor seating Florida Keys
- Rentals with pools Florida Keys
- Boutique hotel rentals Florida Keys
- Rentals with an EV charger Florida Keys
- Houseboat rentals Florida Keys
- Resort rentals Florida Keys
- Rentals with a kayak Florida
- Rentals with a kayak United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Bayfront Park
- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Trump National Doral Miami
- Crandon Beach
- Key Biscayne Beach
- Phillip and Patricia Frost Museum of Science
- Coral Castle
- Hobie Island Beach Park North
- Biscayne National Park
- Fairchild Tropical Botanic Garden
- Cannon Beach
- Conch Key
- Biltmore Golf Course Miami
- Miami Seaquarium
- Venetian Pool
- EAA Air Museum
- Cocoa Plum Beach
- Theater of the Sea
- Everglades Alligator Farm
- Matheson Hammock Park
- Sea Oats Beach
- Things to do Florida Keys
- Sightseeing Florida Keys
- Tours Florida Keys
- Art and culture Florida Keys
- Sports activities Florida Keys
- Things to do Florida
- Nature and outdoors Florida
- Art and culture Florida
- Tours Florida
- Entertainment Florida
- Sightseeing Florida
- Sports activities Florida
- Food and drink Florida
- Wellness Florida
- Things to do United States
- Tours United States
- Entertainment United States
- Sports activities United States
- Food and drink United States
- Sightseeing United States
- Art and culture United States
- Nature and outdoors United States
- Wellness United States