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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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4.92 out of 5 average rating, 133 reviews
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
9–14 Sept
4.94 out of 5 average rating, 81 reviews
Superhost
Tiny home in Summerland Key
Bungalow
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
4.82 out of 5 average rating, 92 reviews
Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom, 4 beds, 1 bathroom
8–13 Sept
4.97 out of 5 average rating, 36 reviews
Featured hotel
Hotel in Summerland Key
Waterfront two bedroom cottage
1 bedroom, 2 king beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 4 reviews
Home in Cudjoe Key
Private Secluded Ocean View & Pool Near Key West
4 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
New place to stay
Top guest favourite
Home in Cudjoe Key
Waterfront, Dock, Pool, Pickleball, near Key West!
2 bedrooms, 3 beds, 1 bathroom
8–13 Sept
4.99 out of 5 average rating, 75 reviews
Guest favourite
Tiny home in Summerland Key
Waterview Bungalow
1 bedroom, 1 king bed, 1 bathroom
9–14 Sept
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Cudjoe Key
Ocean's Edge VO Pad Boards, Kayak, Bikes-30 min KW
2 bedrooms, 4 beds, 1 bathroom
18–23 Oct
4.97 out of 5 average rating, 95 reviews
Featured hotel
Room in Marathon
Three bedroom beachfront villa
4 king beds, 1 bathroom
8–13 Sept
New place to stay
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Cudjoe Key
Betty's Place
2 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.92 out of 5 average rating, 120 reviews
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
Featured hotel
Room in Key West
Marker residences one bedroom suite
2 king beds, 1 bathroom
13–18 Sept
New place to stay
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
9–14 Sept
4.56 out of 5 average rating, 25 reviews
Featured hotel
Room in Key West
Accessible Classic Double Queen City/Balcony
2 queen beds, 1 bathroom
20–25 Sept
4.71 out of 5 average rating, 7 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, 211 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
Home in Cudjoe Key
NEW Listing•Solace by the Sea•37’Dock•Ocean Views
2 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
New place to stay