Holiday 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

Holiday House Rentals with a Kayak

Guest favourite
Home in Marathon
5 out of 5 average rating, 37 reviews

Waterfront Escape -VACA-23-408

NatalieRating, 5 stars2 weeks ago
we were a family of 6 staying and had more then enough room. the house was perfect and had everything you needed. we enjoyed fishing off the deck and watching the manatees everyday day swimming by. the backyard was absolutely perfect to hang out and relax. Carmen is a great host and communicates fast. would absolutely stay here again.
Superhost
Home in Marathon
5 out of 5 average rating, 3 reviews

Waterfront Oasis3/2 Direct Ocean

JohnRating, 5 stars11 months ago
Beautiful views and great spaces! We’ve stayed in Marathon several times in different canal houses with our family of 7, and this property is now our new favorite. We couldn’t get enough of all the beautiful views from sunrise to sunset whether it was on the porch, in the pool, or out by the Tiki Hut. Every bedroom has water views as well. Boat access was an easy out to snorkeling, diving, fishing, or whatever you like to do. There are two kayaks for use, which made for some nice outings to explore the immediate area. The kitchen had everything needed for cooking, and even had an extra under-the-counter ice machine. We had a great time here, and would stay again. Thank you to the owners for sharing your property.
Top Guest favourite
Home in Key Largo
4.97 out of 5 average rating, 161 reviews

Key Largo Waterfront Home with Tiki & Boat Dock

MattRating, 5 stars1 week ago
This is the perfect location for us, we have a small flats boat and there’s great fishing in the area. The weather was not great but were able to find areas to fish sheltered from the wind. When not fishing, hanging out on the dock with Princess, watching the manatees and having a cold drink was absolute paradise. Penny is very responsive and was available anytime needed. This was our second time staying at this location and already talking about booking a longer stay next year.
Guest favourite
Home in Marathon
4.96 out of 5 average rating, 52 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

LoganRating, 5 stars3 weeks ago
The location and access to the beach and canal was amazing! We had such a fun time with the kayaks while being able to see all the wildlife and sail boats. The house was exactly what we needed. Jose was very helpful and flexible throughout our stay.
Guest favourite
Home in Sugarloaf Key
4.81 out of 5 average rating, 114 reviews

The Guest House - Sugarloaf Beach Key West

KimberlyRating, 5 stars3 weeks ago
Upon arrival it was very clean, well taken care of and beds were comfortable sleeping 8 guests - which is not easy to find. Location is quiet, private and driving distance to town is minimal. My husband and I enjoyed walking on the private dock and beach. Tom greeted us right away and was exceptionally helpful anytime we had questions or needed anything at all We look forward to returning.
Superhost
Home in Cudjoe Key
4.83 out of 5 average rating, 264 reviews

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

AlexRating, 5 stars1 month ago
The house was exactly as pictured and in a very peaceful community. The beds were comfortable, as was the couch (two of our group opted to sleep on the couch itself instead of pulling out the sleeper sofa, and said it was pretty comfy!). Several of our group enjoyed using the bikes at night, and while we didn’t use the kayaks, it’s nice they were available. We didn’t get to do everything we hoped to do on our trip to Keys, but we plan to stay here again someday when we come back!
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 34 reviews

Viamarhe House-Private beach, Kayak, yard games

AmandaRating, 5 stars2 weeks ago
Loved our week-long stay at Marjorie’s! As pictured and described. Checked out the other reviews for useful tips.
Guest favourite
Home in Key Largo
4.91 out of 5 average rating, 107 reviews

Sunsets In Palms Paradise

TaylorRating, 5 stars4 weeks ago
We thoroughly enjoyed this house! The backyard is amazing with plenty of space to play cornhole, throw frisbees, and enjoy the beautiful weather. We saw a manatee behind the property and with the provided paddleboard got to see it close up as well! The house was clean and had all desired amenities . We will definitely be back.

Cottages with a kayak

Top Guest favourite
Cottage in Fort Lauderdale
5 out of 5 average rating, 61 reviews

Cozy Tropical Cottage. Your new Happy Place!

ToriRating, 5 stars2 months ago
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 :)
Guest favourite
Cottage in Islamorada
4.97 out of 5 average rating, 86 reviews

Islamorada bungalow 2 bed & pool

DavidRating, 5 stars2 weeks ago
We had a blast at Yasmin and Joe's amazing cottage in the Keys! Perfect size for two couples (or a small family). When we arrived the place was pristine and exceeded our expectations from the photos. If you have a boat, being able to access the community's private ramp is a huge perk, and launching/retrieving the boat was a breeze. 10/10 and we'll be back. Thanks for sharing your property!
Superhost
Cottage in Cudjoe Key
4.8 out of 5 average rating, 5 reviews

Ocean Breeze at Venture Out 537

MelissaRating, 5 stars3 weeks ago
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!
Top Guest favourite
Cottage in Marathon
4.97 out of 5 average rating, 36 reviews

Catch n' Relax Canalfront Cottage in Marathon

StefaniRating, 5 stars1 week ago
We have three boys and they LOVED being able to fish anytime they wanted. We caught over 12 species of fish from the back dock. The kayaks were very handy! We just rented two more and We loved getting out in the mornings for a family kayaking adventure and the boys fished any chance they got. They even caught a nurse shark! The house was clean and well decorated. There were handy items such as sunscreen and life vests. It was a great place for a family of five.
Guest favourite
Cottage in Naples
4.95 out of 5 average rating, 149 reviews

Tropical Cottage by the Sea- No Storm Damage

NanichiRating, 5 stars1 week ago
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!
Guest favourite
Cottage in Cudjoe Key
4.93 out of 5 average rating, 129 reviews

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

DonnaRating, 5 stars1 month ago
We brought another couple with us. Had a relaxing enjoyable time. Felt like home. Definitely be back. Thank you
Guest favourite
Cottage in Hollywood
4.98 out of 5 average rating, 42 reviews

Beautiful 3 bedroom cottage with private rooftop

CarlaRating, 5 stars2 months ago
I stayed at Jeff's place with 4 of my cousins, so 5 girls in the house. We were anticipating a trip just to hang out at a beach for a couple of days and this was a great place to do that. It was a great stay, we were close to the beach. Jeff had beach chairs ready for us and a wagon to pull them to the beach. It was like a half a block walk to the boardwalk and beach. We spent a lot of time walking the boardwalk, checking out the shops and eateries and enjoyed the beautiful sandy beach. Their is a nice bottom deck and top deck which we enjoyed coffee out there in the morning and playing cards later at night. We would definitely come back here or recommend this place. Jeff was very easy to reach out to and responded to texts very well. He even called us the morning we were checking out to make sure everything was OK. NOTE: There are towels in the bathrooms, but no wash cloths and no dish cloths (there is a sponge) and no dish towel. So next time I would pack each of those.
Guest favourite
Cottage in Key Largo
4.91 out of 5 average rating, 86 reviews

THE PARADISE

JessicaRating, 5 stars4 days ago
We were there because we was celebrating my husband‘s birthday and our wedding anniversary . It was a great place to stay highly recommend it. Quiet and comfortable atmosphere for a great long weekend. Luis Alberto and his wife very attentive. It makes us feel like we’re around family.. can’t wait to come back again. Our favorite place to go for now on.

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