
Holiday rentals with a kayak in Key West
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Top-rated rentals with kayak in Key West
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.
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Popular amenities for kayak rentals in Key West
House rentals with a kayak

Waterfront with Boat Lift/Kayaks and Hot Tub
The place was amazing!! plenty of room for our family of 5. All of the fishing equipment was awesome!! From the rods and tackle, to the deep freezer with bait, the extras made the whole trip more enjoyable. Loved the house. It was perfect!!! Will definately be back in the future!! 10 out of 10 would recommend!!

Oceanside, Smart Home with SUP/kayaks - 60 FT Dock
The location was great. It was perfect for me and my husband. Kris was very communicative and replied almost instantly. Definitely would stay again.

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish
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 didnât work properly in some of the rooms, no washcloths or kitchen towels available. With that being said, we will definitely consider renting Ryanâs place again in the future!

Flamingo Palms-Spring discounts-NOW available
Excellent host and great home and location. Fishing from the dock, grill on the patio. Lovely decor throughout the property. Made for an excellent choice for my wifeâs milestone birthday celebration and Ramon and Ana made that extra special with a birthday banner. Would visit again travel plans permitting

Sunset Views, Pool and Dock
Thank you Frank for a great place to stay! Close to restaurants, quite neighborhood, nice pool, a dock to swim and fish from, and beautiful sunsets. We had everything we needed.

White Vacation Home. Free cancellation see details
We had a wonderful stay. The location was perfectâ private, beautiful, great outdoor space! Close to the beach and a quick drive to Key West. The house had everything we needed. The host was welcoming and very very accommodating! Will be back!

Waterfront FL Keys Cottage @ Venture Out
Great location, easy access to everything, lots of amenities on the community.

New Private 4/3 Single Family - Kayaks & Bicycles+
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.
Cottage rentals with a kayak

Islamorada bungalow 2 bed & pool
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!

Ocean Breeze at Venture Out 537
I had a wonderful stay at this Airbnb! The home was perfect for our occasionâjust 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!

1 Bedroom Home in Key Largo
This was such a fun stay! The little beach cottages were so cute. The bedroom is rather tight and the loft is designed for children size guests, but we didn't mind. The kitchen had everything we needed, the dock and beach area were where we spent most of our time outside of wedding festivities, the grill and firepits were a nice touch too. The guy working the whole time we were there was great, he was great with communication and super friendly. Hard worker! I will say we did not get the house from the post- but only the picture of the outside. Which was totally fine, the inside was exactly the same. Another guest in our party had the same experience but didn't get a loft- but if you are like them and didn't need a loft those cabins were actually nicer. I read other reviews stating they didn't get the cabin they requested, but it seemed like there were only a few different variations of exactly the same model with different external design. I'd do it all again!

Catch n' Relax Canalfront Cottage in Marathon
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.

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO
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!

Cottage Sunroom Waterfront Retreat 2 ppl
This place is beautiful with old Florida charm. Will be back!

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

OCEANIA... water front cottage retreat ~
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 sonâs large pickup. Curious as to what that fee actually pays for. We would definitely stay again.
Quick stats about holiday rentals with a kayak in Key West
Total rentals
30 properties
Nightly prices starting at
$141Â SGD 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
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