
Holiday rentals with a kayak in Key West
Find and book unique kayak rentals on Airbnb
Top-rated Accommodation with a Kayak in Key West
Guests agree: these holiday homes with a 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 Key West kayak rentals
Holiday House Rentals with a Kayak

Keys Home, Boat Slip + Golf Cart
Home away from home! Has everything you need. Golf cart was a huge asset! Boys loved it. They would take mini adventures. Brought our own firewood and made s’mores! Just a great experience!

Sunset Views, Pool and Dock
We really liked the location. It was peaceful and private and a great neighborhood to walk around and to walk our dog. Yet, a short drive into Marathon for restaurants or any other needs. The house isn’t new but it was exactly as represented and it was perfect for us. Frank was very responsive. There were a couple of issues that he addressed immediately. It wasn’t his fault that because of the location, receiving repair parts can take some time. But Frank took care of our situations.

Luxury Waterfront Retreat with Dockage & Pool
Had an amazing stay at this house with my husband and 4 small kids. The house was spacious and clean, with lots of natural light at soon as the sun came up. The pool was so warm and had a large shallow area that was perfect for our 3 year old. Naomi was a wonderful communicator. It was so sad to have to leave.. Would definitely recommend staying here.

Large Waterfront Home, w/Efficiency, Pool, Kayaks
Stu’s place was not only beautiful but it had all the amenities we could have asked for. The location was perfect for all the things we wanted to do. It truly was a home away from home. If I could give more than 5 stars I certainly would. Loved it! Stu was extremely easy to communicate with.

Deckhouse
What a great place! The location was easy to find and central to all things Key Largo. Our unit was well equipped, clean and comfortable beds. I saw a dolphin, a manatee and plenty of iguanas sunning themselves. I would return again, and hope you all try this beautiful property

Golf Coast Oasis
Very nice place with excellent amenities. The heated pool was awesome! Worked out great for our family. The only minor issue was the noise from the nearby airport was loud at times and there were frequent construction trucks driving by. We live in rural area with no noise, so we were probably more sensitive to it, but we did get used to it and it wasn't a major problem. We would definitely stay here again.

The Mini Coconut
We had a great experience. The house was clean and beautiful. The area was peaceful and fun. The property caretaker was super responsive and bent over backwards to ensure our satisfaction. I would definitely stay with them again!

Waterfront Heated Pool 120 ft Boat Dock
Milton has to be one of the best hosts on Airbnb! Extremely responsive, very concerned we were more than satisfied with our stay. Thank you for a great stay, Milton.
Cottages with a kayak

Islamorada bungalow 2 bed & pool
Yasmin and Joe were very responsive and friendly in all of their communications. The bungalow was perfect for my daughter, cousin and I. The decorations and amenities were very well done and made you feel very welcome. Having the pool right next door was wonderful. The location is convenient to restaurants, boating activities and shopping. It is a bit close to A1A so there is road noise, but the hosts provide noise makers in the bedrooms which make it all go away. Overall a great place to have a vacation!

1 Bedroom Home in Key Largo
Beautiful cottage, everything you need for a home from home. Great base to explore the keys. Thanks for a wnderful stay

Catch n' Relax Canalfront Cottage in Marathon
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!

Tropical House By The Shore at Largo Resort
Beautiful and very clean accommodation, well furnished, everything you need is included, and also the host was very friendly and helpful. I can recommend this accommodation with a clear conscience.

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO
My husband and I had a great time here! We were amazed at all the fish and manatees we saw! My husband was in heaven getting to fish off the balcony and a manatee swam right up to us and went under the house! Such a cool experience! All the staff we interacted with were super friendly and great! Highly recommend!

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
We loved our stay here! The house was very clean and so well stocked! We felt very safe in the gated community. Our kids loved the bikes, fishing rods, paddle boards, and sports equipment. The host was super friendly and great to give recommendations (that we took!) We had the best week here!

Luxurious Oasis: 2BR w/Pool, Tiki, Dock & Beach
Leeann’s place exceeded our expectations! She was incredibly responsive to any concerns or inquiries we had throughout our stay. The added perk of access to Glunz Beach Resort with its beach, pool, and gym made our experience even more delightful. The house was equipped with everything we needed for a comfortable stay. Thank you, Leeann!

OCEANIA... water front cottage retreat ~
If we could rate this 6+ stars out of 5, we would! Manuel was super easy to reach, he provided simple and clear instructions, the guards at the gate were easy to work with and available for 24/7 entry and check in.. the location is unbeatable for a boat owner! You dock right at your back door, clean your fish at the back door OR at the marina, immediate access to the Atlantic.. perfection. The home itself is extremely clean & beautiful. The kitchen and bathrooms were all stocked with anything you’d need as well as even the laundry room! We truly felt at home but twice as relaxed! Thanks Manuel!!
Quick stats about holiday rentals with a kayak in Key West
Total rentals
20 properties
Nightly prices starting at
$255 AUD before taxes and fees
Total number of reviews
670 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
10 properties have a dedicated workspace
Destinations to explore
- Florida Keys Holiday rentals
- Havana Holiday rentals
- Miami Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Bay Holiday rentals
- St Petersburg Holiday rentals
- Tampa Holiday rentals
- Central Florida Holiday rentals
- Kissimmee Holiday rentals
- Four Corners Holiday rentals
- Rentals with a kayak United States
- Rentals with a kayak Florida
- Rentals with a fire pit Key West
- Kid-friendly rentals Key West
- Beachfront rentals Key West
- Rentals with breakfast Key West
- Beach house rentals Key West
- Houseboat rentals Key West
- Luxury rentals Key West
- Rentals with an accessible height toilet Key West
- Rentals with beach access Key West
- Pet-friendly rentals Key West
- Waterfront rentals Key West
- Rentals with a patio Key West
- House rentals Key West
- Condo rentals Key West
- Fitness-friendly rentals Key West
- Apartment rentals Key West
- Rentals with a washing machine and dryer Key West
- Beach condo rentals Key West
- Rentals with a hot tub Key West
- Rentals with pools Key West
- Rentals with an EV charger Key West
- Family-friendly rentals Key West
- Mansion rentals Key West
- Resort rentals Key West
- Rentals with outdoor seating Key West
- Villa rentals Key West
- Hotel rentals Key West
- Rentals with lake access Key West
- Rentals with a fireplace Key West
- Monthly Rentals Key West
- Cottage rentals Key West
- Townhouse rentals Key West
- Rentals with a kayak Miami-Dade County
- Rentals with a kayak Florida Keys
- Rentals with a kayak Monroe County
- 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
- Things to do Key West
- Art and culture Key West
- Sightseeing Key West
- Tours Key West
- Things to do Monroe County
- Food and drink Monroe County
- Sightseeing Monroe County
- Entertainment Monroe County
- Nature and outdoors Monroe County
- Sports activities Monroe County
- Art and culture Monroe County
- Tours Monroe County
- Things to do Florida
- Wellness Florida
- Food and drink Florida
- Sightseeing Florida
- Nature and outdoors Florida
- Sports activities Florida
- Art and culture Florida
- Tours Florida
- Entertainment Florida
- Things to do United States
- Art and culture United States
- Entertainment United States
- Nature and outdoors United States
- Food and drink United States
- Sports activities United States
- Tours United States
- Sightseeing United States
- Wellness United States