
Holiday rentals with a kayak in Sugarloaf Key
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Top-rated rentals with kayak in Sugarloaf Key
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House rentals with a kayak
Superhost

Home in Marathon
4.89 out of 5 average rating, 18 reviewsSalty kisses beach house
AnaRating, 5 stars3 weeks ago
Had a wonderful time at Salty Kisses. The area was beautiful and we were able to relax with the stunning views of the backyard. The house had everything we needed in the kitchen, bedrooms, bathrooms, and even outside for entertainment. Lazaro was very attentive making sure everything was good. Neighborhood was quiet. We spent a lot of time in the pool, grilling, and out on the water which was easily accessible with the dock at the front of the house. The whole family was in love with the decorations of the house which were truly beautiful and making us feel right at home. Thank you Laz and Leslie!
Guest favourite

Home in Marathon
5 out of 5 average rating, 37 reviewsWaterfront Escape -VACA-23-408
NatalieRating, 5 stars1 week ago
we were a family of 6 staying and had more then enough room. the house was perfect and had everything you needed. we enjoyed fishing off the deck and watching the manatees everyday day swimming by. the backyard was absolutely perfect to hang out and relax. Carmen is a great host and communicates fast. would absolutely stay here again.
Guest favourite

Home in Marathon
5 out of 5 average rating, 17 reviewsSeaside Sunrise. Newly remodeled waterfront
JonathynRating, 5 stars3 months ago
Everything was excellent. Only complaint would be the bicycles. One bike was usable but the seat was loose and we didnāt have tools to fix it. The other adult bikeās chain was rusted so bad it wasnāt usable. We still had an excellent experience.
Top guest favourite

Home in Marathon
5 out of 5 average rating, 41 reviewsDiscount Available! 100' Dock, Lots of Amenities!
DanaRating, 5 stars1 week ago
We came down for a weeks vacation brought two boats, plenty of space on the docks. Communication with Meredith was great. Great location.
Top guest favourite

Home in Key Colony Beach
4.98 out of 5 average rating, 124 reviewsParadise found!Key Colony Beach,Cabana Club.
ColinRating, 5 stars5 days ago
We had a great week at Kari's place. We were blown away by the view from the terrace. The apartment was well appointed and had everything we needed. The use of the nearby Cabana club was a real bonus. Colony Key is about an hour from Key West, so it was well located for all sorts of activities. Would love to return one day. Thanks Kari. Colin & Lynne Moore. Buckinghamshire, UK
Top guest favourite

Home in Marathon
4.98 out of 5 average rating, 47 reviewsFlamingo Palms-Spring discounts-NOW available
LaurenceRating, 5 stars1 month ago
Excellent host and great home and location. Fishing from the dock, grill on the patio. Lovely decor throughout the property. Made for an excellent choice for my wifeās milestone birthday celebration and Ramon and Ana made that extra special with a birthday banner. Would visit again travel plans permitting
Superhost

Home in Cudjoe Key
4.62 out of 5 average rating, 165 reviewsOcean Front Home in Great Location
MichaelRating, 5 stars1 month ago
Fantastic place for a home base while the beautiful keys. Close enough to key west for an upbeat day, very quiet in the evening. If anything, Iād say I was expecting less from the description and was very surprised at how nice this place is. I would stay here again in a heartbeat!
Guest favourite

Home in Cudjoe Key
4.95 out of 5 average rating, 20 reviewsSea Turtle Cove
ThomRating, 5 stars1 month ago
Philip's listing described the place perfectly. Zero unexpected surprises and it had absolutely everything to make our vacation super enjoyable. When it comes to location, so much to do in under 30 minutes. Smack dab in the middle when it comes to driving to Marathon or Key West. It was also great to be able to keep a boat right outside and to have a marina as part of the park. Access to great places to fish are 15-30 minutes away.
Cottage rentals with a kayak
Guest favourite

Cottage in Islamorada
4.96 out of 5 average rating, 85 reviewsIslamorada bungalow 2 bed & pool
AmandaRating, 5 stars4 days ago
The hosts were very responsive and accommodating to our needs. The pool was great and the place was pristine!

Cottage in Key Largo
4.75 out of 5 average rating, 16 reviews1 Bedroom Home in Key Largo
HollyRating, 5 stars5 days ago
This was such a fun stay! The little beach cottages were so cute. The bedroom is rather tight and the loft is designed for children size guests, but we didn't mind. The kitchen had everything we needed, the dock and beach area were where we spent most of our time outside of wedding festivities, the grill and firepits were a nice touch too. The guy working the whole time we were there was great, he was great with communication and super friendly. Hard worker! I will say we did not get the house from the post- but only the picture of the outside. Which was totally fine, the inside was exactly the same. Another guest in our party had the same experience but didn't get a loft- but if you are like them and didn't need a loft those cabins were actually nicer. I read other reviews stating they didn't get the cabin they requested, but it seemed like there were only a few different variations of exactly the same model with different external design. I'd do it all again!
Guest favourite

Cottage in Marathon
4.97 out of 5 average rating, 35 reviewsCatch n' Relax Canalfront Cottage in Marathon
StefaniRating, 5 stars2 days ago
We have three boys and they LOVED being able to fish anytime they wanted. We caught over 12 species of fish from the back dock. The kayaks were very handy! We just rented two more and We loved getting out in the mornings for a family kayaking adventure and the boys fished any chance they got. They even caught a nurse shark! The house was clean and well decorated. There were handy items such as sunscreen and life vests. It was a great place for a family of five.

Cottage in Islamorada
4.75 out of 5 average rating, 175 reviewsFLOATING 1BD 1BA PRIVATE COTTAGE - MAKO
JaceyRating, 5 stars4 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
4.58 out of 5 average rating, 715 reviewsCottage Sunroom Waterfront Retreat 2 ppl
TracyRating, 5 stars1 week ago
This place is beautiful with old Florida charm. Will be back!

Cottage in Key Colony Beach
5 out of 5 average rating, 11 reviewsLuxurious Oasis: 2BR w/Pool, Tiki, Dock & Beach
MatthewRating, 5 stars1 month 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!

Cottage in Cudjoe Key
4.82 out of 5 average rating, 98 reviewsOCEANIA... water front cottage retreat ~
DeniseRating, 5 stars1 month ago
Place was great. We loved the kayaks and Bikes that were there. Very clean and spacious. Beautiful view being on the canal. my negative I would say, which has nothing to do with the host, We were aware of the $125 resort fee, And our fee was increased to $145 cause my sonās large pickup. Curious as to what that fee actually pays for. We would definitely stay again.
Superhost

Cottage in Cudjoe Key
4.71 out of 5 average rating, 152 reviewsCalypso Cottage
JenniferRating, 5 stars2 weeks ago
Everything was perfect! I loved the screened in front porch! We spent a lot of time out there and the back was so peaceful for watching the sun come up with my morning cup of coffee. The staff at the resort were super friendly and helpful and I notice security was constantly driving around which made it feel safe and taken care of. Everyone at the resort looked so happy and relaxed! The pool!!! I didnāt want to leave and it has great hours! We were able to explore the area and still had time to go swimming at the poolā¦under the stars! It was a wonderful experience. Plan to some time go back and plan the whole trip staying there!
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