Vacation rentals with a kayak in Sugarloaf Key

Find and book unique kayak rentals on Airbnb

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Popular amenities for Sugarloaf Key kayak rentals

House rentals with a kayak

Guest favorite

Home in Key Colony Beach

5 out of 5 average rating, 5 reviews

Keys Dream~ 37' Dock, Kayaks, Beach Club Included!

JenniferRating, 5 stars6 months ago
Loved the location. The kayaks and paddle boards were a hit. The easy access to ocean while renting a boat was great! Enjoyed riding the bikes and enjoying the local sunset beach to watch the sunset.
Guest favorite

Home in Marathon

5 out of 5 average rating, 37 reviews

100' Dockage, Pool, Kayaks, Paddle Board, Bikes!

AmyRating, 5 stars3 weeks ago
We have enjoyed our time! The pool was excellent and the back yard very private, which was wonderful! Close walk to the beach and near walking paths. Had to drive to restaurants, but plenty of options w/in 10 min. Living space great, beds comfy. Floaties and kayaks in the garage, we used both. Caught some fish off the back canal, we even ate some! Would stay here again!
Superhost

Home in Marathon

4.81 out of 5 average rating, 31 reviews

Luxury Waterfront Retreat with Dockage & Pool

DonRating, 5 stars1 day ago
Last minute booking with Naomi due to problem with another Airbnb on Cudjoe Key. Naomi immediately responded and made arrangements to get us settled. Her place was easy to find, with a lot of amenities provided. Kayaks, hot tub, pool and fishing were easy to access and enjoy.
Superhost

Home in Cudjoe Key

4.79 out of 5 average rating, 19 reviews

Keys Time #437 - Cudjoe Key, Oceanfront Community

EmilieRating, 5 stars1 month ago
The property was exactly as described. We even saw manatee in the channel each morning. Our host was very responsive when we had an issue and took care of it within hours. Great property and good amenities.
Guest favorite

Home in Marathon

4.96 out of 5 average rating, 23 reviews

Waterfront w/pool and hot tub

ValerieRating, 5 stars2 weeks ago
A nice location in Key Colony Beach along a canal. Close to sunset park. The house was great for a weeklong stay. Some restaurants within walking distance and a great neighborhood for exercising.
Guest favorite

Home in Cudjoe Key

4.93 out of 5 average rating, 15 reviews

Oceanside home 107,dock,kayaks,bikes,pool,fishing,

DoriRating, 5 stars1 month ago
Great location with proximity to Key West and Big Pine. Loved the included recreation options (bikes, kayaks). The place was so nice and the pictures didn’t do it justice/ the place is so nicely decorated and looks even better in person !
Guest favorite

Home in Marathon

4.87 out of 5 average rating, 15 reviews

Golf Coast Oasis

ShannonRating, 5 stars2 weeks ago
This was my second time staying at gulf coast oasis, and it was amazing again. You can tell that the owners take great care of the house and property, and they are super responsive and reach out proactively. It’s a fantastic location in Marathon which is central to restaurants and local activities. The house itself is stocked with everything you need to feel at home. It’s secluded/fully fenced, has tons of amenities (heated pool, putting green, kayaks, bikes, grill, fire pit, comfy indoor and outdoor seating). The kitchen is stocked with everything you need like a Keurig and kcups, pans and gadgets and utensils for cooking, loads of spices. Memory foam beds are comfy. They have extra little touches throughout like toiletries, games, fans, tons of beach towels, pool toys. We saw manatees in the canal, birds and lizards around the property. I can’t say enough good things about this house. My group included 2 couples and 2 dogs. We were comfortable, relaxed, and had a fun stay.
Guest favorite

Home in Marathon

5 out of 5 average rating, 23 reviews

Sale! Cabana Club, Kayaks, Dock, Pet Friendly

MichelleRating, 5 stars3 weeks ago
We had a fantastic stay at Coral Cabana in the Florida Keys! The location was perfect, with stunning views that made every morning feel like paradise. The house was clean and comfortable, providing everything we needed for a relaxing getaway. Bert, our host, was incredibly responsive and made sure we had everything we needed during our stay. His attentiveness truly enhanced our experience. Overall, we had a great time and would absolutely stay here again. Highly recommend!

Cottage rentals with a kayak

Cottage in Cudjoe Key

4.81 out of 5 average rating, 95 reviews

OCEANIA... water front cottage retreat ~

RachelRating, 5 stars4 months ago
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!!
Guest favorite

Cottage in Islamorada

4.97 out of 5 average rating, 65 reviews

Islamorada bungalow 2 bed & pool

KinoRating, 5 stars3 weeks ago
Absolutely great experience! Beautiful landscaping, house is clean, kitchen is well stocked, clean linen, soft bedding, host provided beach towels, bath towels, complimentary toiletry, etc. We were able to enjoy the outdoor grill, fire ring, porch.. my kids loved the swimming pool, which is right next to our bungalow. Our hosts are super responsive and proactively communicated with me about house keeping rules, local to-do, restaurants, etc, all of which I found extremely helpful. When I needed a recommendation for a beach, they were quick to respond too. Special thanks because I somehow left my wallet behind and they helped me locate it and recovered my loss. Everything is functioning, like new condition. We had a lot of fun, definitely worth coming back!

Cottage in Cudjoe Key

4.71 out of 5 average rating, 136 reviews

Calypso Cottage

CoriRating, 5 stars1 week ago
Exactly as described and good location. About 30-45 minutes from Key West activities and a lot of stuff to do at the house - we loved the kayaks, bikes, and pool.
Superhost

Cottage in Islamorada

4.78 out of 5 average rating, 169 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

KatharineRating, 5 stars3 weeks ago
This AirBnB was a wonderful escape from reality! We hope to visit again at some point.

Cottage in Key Colony Beach

5 out of 5 average rating, 10 reviews

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

DawnRating, 5 stars9 months ago
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!

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