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 favourite
Home in Marathon
5 out of 5 average rating, 38 reviews

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

AmyRating, 5 stars3 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 favourite
Home in Marathon
4.95 out of 5 average rating, 131 reviews

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

JenniferRating, 5 stars3 days 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
4.79 out of 5 average rating, 34 reviews

Luxury Waterfront Retreat with Dockage & Pool

MindyRating, 5 stars1 month ago
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.
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 stars14 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 favourite
Home in Marathon
4.94 out of 5 average rating, 32 reviews

Waterfront w/pool and hot tub

ErinRating, 5 stars3 weeks 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, 19 reviews

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

JessicaRating, 5 stars3 weeks 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 reviews

Fun 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.

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 favourite
Cottage in Islamorada
4.96 out of 5 average rating, 78 reviews

Islamorada bungalow 2 bed & pool

AaronRating, 5 stars2 weeks ago
It's a beautiful place with so much to do. I enjoyed the bikes and trying out some local places. The cottage was very clean and comfortable. Yasmin and Joe are great, very responsive and had some great suggestions for things to do. The pool there is a lovely little gem.
Superhost
Cottage in Cudjoe Key
4.7 out of 5 average rating, 145 reviews

Calypso Cottage

CourtneyRating, 5 stars1 week 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 stars2 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!
Private room in Key Largo
4.57 out of 5 average rating, 701 reviews

Cottage Sunroom Waterfront Retreat 2 ppl

KellyRating, 5 stars2 weeks ago
A beautiful eclectic resort with so much charm and lots of amenities. I will definitely be back! Leslie was amazing and her place is a little slice of paradise.
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!
Superhost
Cottage in Cudjoe Key
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