
Vacation rentals with a kayak in Sugarloaf Key
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Top-rated kayak rentals in Sugarloaf Key
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House rentals with a kayak

Discount Available! 100' Dock, Lots of Amenities!
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!

Luxury Waterfront Retreat with Dockage & Pool
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!

Waterfront Oasis3/2 Direct Ocean
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.

Dolfan Oceanfront Cottage Direct oceanfront with 5
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

Deckhouse
Absolutely amazing! Tanya’s Airbnb was the perfect venue for our wedding. The space was stunning, beautifully maintained, and created the most magical atmosphere for our special day. Tanya and Lana were incredible hosts—responsive, accommodating, and truly went above and beyond to make sure everything was perfect. Our guests couldn’t stop raving about the beautiful setting and how comfortable the stay was. If you’re looking for a dreamy location with a fantastic host, this is it! Highly recommend! Let me know if you’d like any tweaks!

Keys Time #437 - Cudjoe Key, Oceanfront Community
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

Waterfront w/pool and hot tub
We had a great time at this location. They had everything we needed and Key Colony is a perfect spot to vacation.

Oceanside home 107,dock,kayaks,bikes,pool,fishing,
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!
Cottage rentals with a kayak

Islamorada bungalow 2 bed & pool
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.

Ocean Breeze at Venture Out 537
It was great! Everything was as amazing!

1 Bedroom Home in Key Largo
Our stay was truly relaxing and worry free. We brought our dog with us which was nice since the place was very dog friendly! Checking in/out was very easy and we felt very safe. The thing I appreciated the most about our stay was on incredibly bug free the property was, especially for being right on the water!

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 just as beautiful as in the pictures or more. The view is stunning with two swimmable “lagoons”, paddle boarding and Kayaking are super affordable to add on, easy to access and use. The water are was gorgeous, safe and calm. You really do feel like you’re in an oasis, not to mention the epic view of the sunset! Of you’re looking for a peaceful getaway or romantic vibe I highly recommend. Joyce and Leslie are amazing hosts with punctual responses, a warm welcome when you arrive and full of recommendations. Make sure you follow instructions in the welcome packet for more information on your stay and the arrival. That has all of the arrival information and tips for your stay. I’d stay there over and over again. Will definitely be back. Enjoy!

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 ~
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!!

Calypso Cottage
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
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