
Holiday rentals with a kayak in Sugarloaf Key
Find and book unique kayak rentals on Airbnb
Top-rated Accommodation with a Kayak in Sugarloaf Key
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Sugarloaf Key kayak rentals
Holiday House Rentals with a Kayak
Top Guest favourite

Home in Marathon
5 out of 5 average rating, 39 reviewsDiscount Available! 100' Dock, Lots of Amenities!
KatieRating, 5 stars1 week ago
We loved our stay here! The house was perfect for our family. Very roomy and comfy. The backyard was our favorite! We enjoyed nonstop days of relaxing on the patio and in the pool and also fishing/kayaking in the canal. They had everything you could think of that you’d need. The location was great too. Down a quiet dead end road, within walking distance to an amazing beach and just over a mile to Publix. We enjoyed evening bike rides down to the beach which were also provided with the house. We have recommended this place to our fiends and family and hope to come back again ourselves!
Superhost

Home in Marathon
4.81 out of 5 average rating, 36 reviewsLuxury Waterfront Retreat with Dockage & Pool
KathrynRating, 5 stars4 days ago
We had a wonderful family vacation at Naomi’s place. The place was perfect for our family of 4. There was so much to do to keep our active family busy. The house was well stocked with everything you may need for meals. Host was very responsive and helpful throughout our stay. We rented a boat and the dock was perfect for storing. We are looking forward to staying here again on our next visit to the keys!
Superhost

Home in Marathon
5 out of 5 average rating, 3 reviewsWaterfront Oasis3/2 Direct Ocean
JohnRating, 5 stars9 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.
Superhost

Home in Marathon
4.86 out of 5 average rating, 7 reviewsDolfan Oceanfront Cottage Direct oceanfront with 5
ShawnRating, 5 stars15 months ago
This place was great. We close our business down every year for a week so staff can get away and every year some join us for a getaway. This year we came here, the Dolfan house was awesome. The view was amazing and having a boat dock to park the rental boat made it all the better. Idaho’s # 1 steakhouse (Wolf Lodge Steakhouse) will be back next year. Thank You
Superhost

Home in Cudjoe Key
4.81 out of 5 average rating, 21 reviewsKeys Time #437 - Cudjoe Key, Oceanfront Community
FernandaRating, 5 stars6 days ago
We love the hosting! It was an amazing moment together with my family 🩵✨ The cleanliness was spectacular, besides the location! We’ll be back for sure
Guest favourite

Home in Marathon
4.94 out of 5 average rating, 32 reviewsWaterfront w/pool and hot tub
ErinRating, 5 stars1 month ago
We had a great time at this location. They had everything we needed and Key Colony is a perfect spot to vacation.
Guest favourite

Home in Cudjoe Key
4.95 out of 5 average rating, 20 reviewsOceanside home 107,dock,kayaks,bikes,pool,fishing,
JessicaRating, 5 stars1 month ago
If you are looking for a relaxing and peaceful location, this is the place! John was so helpful! The place was exactly as described. Our family felt right at home and enjoyed being away from the busyness of larger keys! Close to Key West and some amazing restaurants!
Guest favourite

Home in Key Colony Beach
4.87 out of 5 average rating, 15 reviewsFun in the Sun!
BrentRating, 5 stars1 month ago
Great attached townhome/duplex with privacy fence between the other side. Great private pool just on the canal! The bottom story was perfect for extended family to have privacy but still be close! We even saw a manatee in the canal.
Cottages with a kayak

Cottage in Cudjoe Key
4.81 out of 5 average rating, 95 reviewsOCEANIA... water front cottage retreat ~
RachelRating, 5 stars7 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 favourite

Cottage in Islamorada
4.96 out of 5 average rating, 80 reviewsIslamorada bungalow 2 bed & pool
MoiraRating, 5 stars2 weeks ago
Very clean and hosts are very responsive. Couldn't find the toaster that was listed. Nice to have beach towels to use for the pool located next door or when going to the beach. Enjoyed having a cooler, beach chairs and umbrella to use for a beach outing. Loved the backyard with a fire pit and Adirondack chairs however the highway runs right behind it and it was a bit noisy. The pool next door was very clean and relaxing. We enjoyed our stay and the recommendations for restaurants and things to do in the area.
Superhost

Cottage in Cudjoe Key
New place to stayOcean Breeze at Venture Out 537
TessaRating, 5 stars4 days ago
It was great! Everything was as amazing!
Superhost

Cottage in Cudjoe Key
4.7 out of 5 average rating, 145 reviewsCalypso Cottage
CourtneyRating, 5 stars2 weeks ago
Place was exactly like described, super quaint and had a great homey cottage feel. Neighbors were all super friendly as well. We really enjoyed being able to sit outside on the canal and enjoy our breakfast/dinner as well as playing any games. Would highly recommend this place, not far from key west a matter of 35-45 min depending on traffic

Cottage in Islamorada
4.75 out of 5 average rating, 175 reviewsFLOATING 1BD 1BA PRIVATE COTTAGE - MAKO
JaceyRating, 5 stars3 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!

Cottage in Key Colony Beach
5 out of 5 average rating, 11 reviewsLuxurious Oasis: 2BR w/Pool, Tiki, Dock & Beach
MatthewRating, 5 stars2 weeks 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!
Destinations to explore
- Key West Holiday rentals
- 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
- Seminole Holiday rentals
- Tampa Holiday rentals
- Central Florida Holiday rentals
- House rentals Sugarloaf Key
- Rentals with beach access Sugarloaf Key
- Family-friendly rentals Sugarloaf Key
- Rentals with outdoor seating Sugarloaf Key
- Rentals with a fire pit Sugarloaf Key
- Rentals with a washing machine and dryer Sugarloaf Key
- Rentals with a patio Sugarloaf Key
- Rentals with pools Sugarloaf Key
- Waterfront rentals Sugarloaf Key
- Pet-friendly rentals Sugarloaf Key
- Rentals with a kayak Monroe County
- Rentals with a kayak Florida
- Rentals with a kayak United States
- 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