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Search results; Over 1,000 homes in Upper Sugarloaf Key

Superhost
Home in Upper Sugarloaf Key
The Lighthouse - Beach Houses Key West
2 bedrooms, 3 beds, 1 private bathroom
26 Sept – 1 Oct
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4.93 out of 5 average rating, 134 reviews
Superhost
Tiny home in Summerland Key
Bungalow
1 bedroom, 2 beds, 1 bathroom
19–24 Sept
4.82 out of 5 average rating, 94 reviews
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
15–20 Sept
4.94 out of 5 average rating, 81 reviews
Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom, 4 beds, 1 bathroom
15–20 Sept
4.97 out of 5 average rating, 36 reviews
Guest favourite
Tiny home in Summerland Key
Waterview Bungalow
1 bedroom, 1 king bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Summerland Key
4BR Villa | Private Pool & Tiki | 30 Min to KW
4 bedrooms, 9 beds, 4 bathrooms
25–30 Oct
4.95 out of 5 average rating, 39 reviews
Guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
1 bedroom, 3 beds, 1 bathroom
13–18 Oct
4.95 out of 5 average rating, 39 reviews
Featured hotel
Hotel in Key West
Classic Double Queen City/Balcony
1 bedroom, 2 queen beds, 1 bathroom
14–19 Sept
4.81 out of 5 average rating, 74 reviews
Luxe
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
15–20 Sept
4.56 out of 5 average rating, 25 reviews
Superhost
Apartment in Summerland Key
Standard Suite at Sugarloaf Key Hotel
1 bedroom, 2 beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Villa in Summerland Key
6BR Villa + Bungalow | Pool & Tiki | 30 Min to KW
6 bedrooms, 7 beds, 6 bathrooms
25–30 Oct
5.0 out of 5 average rating, 12 reviews
Home in Cudjoe Key
Private Secluded Ocean View & Pool Near Key West
4 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
New place to stay
Featured hotel
Hotel in Key West
Havana 2 queens
1 bedroom, 2 queen beds, 1 bathroom
14–19 Sept
Guest favourite
Home in Summerland Key
9BR Estate | 3 Homes/2 Pools/Hot tub -30 Min to KW
9 bedrooms, 16 beds, 9 bathrooms
26–31 Oct
5.0 out of 5 average rating, 19 reviews
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds, 3 bathrooms
2–7 Nov
4.83 out of 5 average rating, 112 reviews
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds, 2 bathrooms
24–29 Oct
4.96 out of 5 average rating, 212 reviews
Guest favourite
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 1 bathroom
14–19 Sept
4.93 out of 5 average rating, 127 reviews
Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds, 1 bathroom
14–19 Sept
4.71 out of 5 average rating, 35 reviews