Holiday rentals with a kayak in Key West

Find and book unique kayak rentals on Airbnb

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Popular amenities for Key West kayak rentals

Holiday House Rentals with a Kayak

Guest favourite
Home in Cudjoe Key
4.86 out of 5 average rating, 14 reviews

Blue Vacation Home. Free cancellation policy

RachelRating, 5 stars5 months ago
Terrific vacation location!!! Mitch and Lu (and Richie) were the absolute best hosts, sharing favorite local spots, tips, and tricks. The location is beautiful and private, yet close to everything, and the house has everything you could need! Would definitely recommend this property and we cannot wait to spend another week here!
Superhost
Home in Marathon
5 out of 5 average rating, 8 reviews

Discount Availble! 3BR 2.5BA Direct to Ocean!

SydneyRating, 5 stars5 months ago
This home offers so many amenities!! We thoroughly enjoyed biking, kayaking, the heated pool, grilling, and several games the host had for us. The large kitchen made it easy for our group of 6 to interact and enjoy meals together. The host was very responsive with any questions we had and checked in throughout the stay to ensure our needs were being met. This was our second year staying in Marathon, would stay at this location again.
Guest favourite
Home in Marathon
4.95 out of 5 average rating, 136 reviews

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish

TashaRating, 5 stars1 week ago
Plenty of room for all the family and their families. We enjoyed all the backyard amenities with pool, kyacks, boat dockage and fish cleaning station. There was sufficient seating for everyone and a great area to hangout. The only things we struggled with was TVs didn’t work properly in some of the rooms, no washcloths or kitchen towels available. With that being said, we will definitely consider renting Ryan’s place again in the future!
Guest favourite
Home in Key Colony Beach
4.94 out of 5 average rating, 50 reviews

Sea Glass Beach Bungalow in Key Colony Beach!

SallyRating, 5 stars2 weeks ago
Our family enjoyed our stay here. Very peaceful setting and we were able to ride the bikes provided by hosts to the beach nearby. The backyard of home offered outdoor relaxation and privacy. The grill worked great too. The home was very clean and comfortable. It is decorated so cute. All kitchen utensils were provided so made cooking meals easy. We did eat out often at nearby keys and the drive was not too far from where we stayed. Lindsey was a great host. She is very responsive and friendly. She checked in to make sure our stay was going well and gave us good info for our stay. We really enjoyed staying here and if we make it back to Key Colony will plan to stay here again. I strongly recommend staying here.
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.
Superhost
Home in Cudjoe Key
4.88 out of 5 average rating, 32 reviews

Waterfront FL Keys Cottage @ Venture Out

ElizabethRating, 5 stars1 week ago
Great location, easy access to everything, lots of amenities on the community.
Top Guest favourite
Home in Marathon
5 out of 5 average rating, 76 reviews

New Private 4/3 Single Family - Kayaks & Bicycles+

SusanRating, 5 stars2 months ago
Our gals trip was wonderful. The pool, ping pong table, corn hole, kayaks, nice bikes, and paddle boards were great amenities to have. The home is located just a couple blocks from Sombrero Beach. All of the outdoor patio furniture was great quality. Nice appliances all around. The beds were very comfortable.
Top Guest favourite
Home in Marathon
4.98 out of 5 average rating, 55 reviews

Waterfront Heated Pool 120 ft Boat Dock

Gwen And JustinRating, 5 stars1 week ago
A Hidden Gem – Perfection in Every Way! Truly! This was, one of the best Airbnbs we have been to in Marathon! We have traveled down for many years and could not ask for a better place!!! From the moment we arrived, everything was absolutely perfect. The space was spotless, it slept 8 of us comfortably! Stocked with every single thing we could need! Location itself was Unbeatable! Peaceful, picturesque, and close to everything, yet somehow still felt like our own private escape! The dock cutting board and easy water hose worked perfect for any catch! The wrap around deck was the biggest hit! Seeing manatees and Tarpon sightings really made my kids day! It truly was magical experience! The pool to cool off and the mini splits in each room without it being manually controlled was the ultimate! Milton was phenomenal to communicate with! You can tell he genuinely cares about his guests♥️. Our family has already booked for next year and we highly recommend!

Cottages with a kayak

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.
Cottage in Islamorada
4.75 out of 5 average rating, 175 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

JaceyRating, 5 stars4 months ago
We loved staying here for the two nights we were on the Keys. The patio outside was great for looking at the stars or sipping coffee and watching manatees. We would definitely return!
Private room in Key Largo
4.58 out of 5 average rating, 715 reviews

Cottage Sunroom Waterfront Retreat 2 ppl

TracyRating, 5 stars3 weeks ago
This place is beautiful with old Florida charm. Will be back!
Cottage in Key Colony Beach
5 out of 5 average rating, 11 reviews

Luxurious Oasis: 2BR w/Pool, Tiki, Dock & Beach

MatthewRating, 5 stars2 months ago
What a fantastic place to stay in Marathon! LeeAnn really makes sure you feel right at home. Forgot a toothbrush? Didn't pack or want to buy shampoo? No problem, it's there! The pool is amazing, house is spotless, and the Key Colony Beach community is the best. It is quiet and relaxing while also being in the heart of everything to do in the Florida Keys. LeeAnn is so nice and responsive, she got back to us quickly with any questions that we had. Overall, this was one of the nicest places that my family and I have ever stayed on a vacation. 10/10 would recommend to anyone!
Cottage in Cudjoe Key
4.81 out of 5 average rating, 99 reviews

OCEANIA... water front cottage retreat ~

DeniseRating, 5 stars1 month ago
Place was great. We loved the kayaks and Bikes that were there. Very clean and spacious. Beautiful view being on the canal. my negative I would say, which has nothing to do with the host, We were aware of the $125 resort fee, And our fee was increased to $145 cause my son’s large pickup. Curious as to what that fee actually pays for. We would definitely stay again.
Superhost
Cottage in Cudjoe Key
4.71 out of 5 average rating, 152 reviews

Calypso Cottage

JenniferRating, 5 stars3 weeks ago
Everything was perfect! I loved the screened in front porch! We spent a lot of time out there and the back was so peaceful for watching the sun come up with my morning cup of coffee. The staff at the resort were super friendly and helpful and I notice security was constantly driving around which made it feel safe and taken care of. Everyone at the resort looked so happy and relaxed! The pool!!! I didn’t want to leave and it has great hours! We were able to explore the area and still had time to go swimming at the pool…under the stars! It was a wonderful experience. Plan to some time go back and plan the whole trip staying there!

Quick stats about holiday rentals with a kayak in Key West

  • Total rentals

    30 properties

  • Nightly prices starting at

    $170 AUD before taxes and fees

  • Total number of reviews

    1.3K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Rentals with a pool

    20 properties have a pool

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Key West
  6. Rentals with a kayak