
Upper Sugarloaf Key vacation rentals
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Top-rated vacation rentals in Upper Sugarloaf Key
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Other great vacation rentals in Upper Sugarloaf Key
Guest favorite

Home in Key Colony Beach
5 out of 5 average rating, 5 reviewsHuge Swim Spa~ Incredible Special Fall Pricing
MatthewRating, 5 stars1 month ago
We really enjoyed our stay. The host, Sherry, gave timely information and quickly responded to messages. We were pleasantly surprised by the number of amenities that were available to us at the house. The Cabana Club was a real hit with my teenage daughters. It had reasonably priced drinks and lunch type meals. They enjoyed just laying by the pool or beach and sun tanning. We saw manatees one of the evenings right in the backyard of the home.
Guest favorite

Apartment in Key West
5 out of 5 average rating, 6 reviewsCasa Caribe 2bed2bath sleeps 6 beautiful decorated
Norma (Jezrael)Rating, 5 stars1 month ago
Judy’s place was one of my favorite we’ve stayed at. She was extremely responsive and helpful. She went above and beyond to accommodate us and we couldn’t be more grateful. Thank you for making our trip so wonderful Judy!
Superhost

Home in Cudjoe Key
4.91 out of 5 average rating, 110 reviewsSunrise Beach Escape
KimberlyRating, 5 stars1 month ago
The place was really nice. One thing that I didn't like was that the beach really wasn't a beach and to get to the water there was just a little walkway and trying to get the kayak down to the water it was a little hard. The pool needs more lights, so it is easier to see. Also, we had a really hard time with the TV's getting them to work. The king size bed was really comfortable. There were lots to see and do and the place really wasn't too far from Key West so not a bad drive.
Top guest favorite

Camper/RV in Key Largo
4.97 out of 5 average rating, 37 reviewsParadise Key Largo
DeannaRating, 5 stars3 weeks ago
Our family of 5 just returned from vacation. My toddlers loved the pool and all the hammocks near the water. Niurka was responsive to any questions we had and gave local recommendations on where to take the kids. We had a great time and will definitely return.
Superhost

Home in Marathon
4.75 out of 5 average rating, 4 reviewsSeaEsta! Bring your boat & 1 block to the beach!
KellyRating, 5 stars1 month ago
Our stay at John's place was amazing. The location was perfect as we went up and down the Keys spending time in Islamorada and a day in Key West. We walked the neighborhood and to Sombrero Beach. The set up for our boat was fabulous. We were able to leave it in the water to use everyday. The best part of John's house was the outdoor area in back. We stayed out there more than anywhere, of course the weather was perfect. Thank you for sharing your place with us John. We hope to be back!
Superhost

Vacation home in Cudjoe Key
4.67 out of 5 average rating, 46 reviewsCrystal Clear Water Getaway!
Shane Rating, 5 stars3 weeks ago
Good place! Clean and close to everything! Thanks
Top guest favorite

Home in Marathon
4.94 out of 5 average rating, 53 reviewsParadise Found! Oceanfront home & amazing sunrises
KimRating, 5 stars1 month ago
Place was great, location, clean and ocean views awesome all around. Fishing was good out back caught a nurse shark, snappers and other small fish. Kayaks were excellent to get out front for mangrove and snook fishing. Definitely recommend !
Guest favorite

Home in Key Colony Beach
5 out of 5 average rating, 10 reviewsSleeps 8, 3 bedroom, 4 full bath, pool, 37.5' dock
JeffreyRating, 5 stars7 months ago
Excellent location in a quiet upscale neighborhood. The house was like new, everything was clean and fresh. Very well equipped kitchen and baths. Lots of space indoors and out, with a beautiful small pool! Would definitely recommend this property for a peaceful getaway in the heart of the Florida Keys!!!
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