Vacation rentals with a kayak in Sugarloaf Key

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Popular amenities for Sugarloaf Key kayak rentals

House rentals with a kayak

Top guest favorite
Home in Marathon
5 out of 5 average rating, 38 reviews

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

AmyRating, 5 stars4 months 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!
Guest favorite
Home in Marathon
4.95 out of 5 average rating, 132 reviews

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish

JenniferRating, 5 stars1 week ago
Although the place wasn’t ready when we arrived, Ryan was a great communicator! He addressed every issue we had (which were NOT within his control) and responded in a timely manner. He offered a fair solution and allowed us to sit back, relax and enjoy paradise! I’d highly recommend and hope to be back sometime soon!
Superhost
Home in Marathon
4.75 out of 5 average rating, 24 reviews

Sunset Views, Pool and Dock

JamesRating, 5 stars1 week ago
We stayed at Frank’s place for two weeks and had an absolutely amazing time! The house was spotless, well-equipped, and super practical for our two energetic little ones. The pool and hot tub were perfect. We made the most of every sunset soaking in the hot tub, followed by peaceful late-night floats in the pool under clear, starry skies. We fished off the jetty most days and caught barracuda, mangrove snapper, plenty of sharks—and the neighbors even hooked a tarpon and landed a grouper! The kids loved snorkeling right off the dock, spotting rays, turtles, and loads of colorful fish. We missed the manatees when they came by one morning, but luckily caught up with them later while kayaking through the mangroves. Huge thanks to Frank for being such a fantastic host. One day we had a small issue with the pool, and his team showed up in under 10—absolutely amazing service. We truly didn’t want to leave and would come back in a heartbeat. Highly recommended!
Superhost
Home in Marathon
4.81 out of 5 average rating, 36 reviews

Luxury Waterfront Retreat with Dockage & Pool

KathrynRating, 5 stars2 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 reviews

Waterfront 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 reviews

Dolfan 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
Guest favorite
Home in Marathon
4.94 out of 5 average rating, 32 reviews

Waterfront 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 favorite
Home in Cudjoe Key
4.95 out of 5 average rating, 20 reviews

Oceanside 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!

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 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 favorite
Cottage in Islamorada
4.96 out of 5 average rating, 80 reviews

Islamorada 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 stay

Ocean Breeze at Venture Out 537

TessaRating, 5 stars2 days ago
It was great! Everything was as amazing!
Superhost
Cottage in Cudjoe Key
4.7 out of 5 average rating, 145 reviews

Calypso 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 reviews

FLOATING 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, 10 reviews

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

DawnRating, 5 stars12 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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