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

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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
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Guest favourite
Tiny home in Summerland Key
Bungalow
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.82 out of 5 average rating, 92 reviews
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Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
4.94 out of 5 average rating, 80 reviews
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Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom, 4 beds, 1 bathroom
1–6 Sept
4.97 out of 5 average rating, 36 reviews
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Guest favourite
Tiny home in Summerland Key
Waterview Bungalow
1 bedroom, 1 king bed, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 19 reviews
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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, 37 reviews
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Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
7–12 Sept
4.56 out of 5 average rating, 25 reviews
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Guest favourite
Villa in Summerland Key
6BR Villa + Bungalow | Pool & Tiki | 30 Min to KW
6 bedrooms, 7 beds, 6 bathrooms
7–12 Sept
5.0 out of 5 average rating, 12 reviews
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Guest favourite
Home in Summerland Key
9BR Estate | 3 Homes/2 Pools/Hot tub -30 Min to KW
9 bedrooms, 16 beds, 9 bathrooms
7–12 Sept
5.0 out of 5 average rating, 18 reviews
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Superhost
Apartment in Summerland Key
Standard Suite at Sugarloaf Key Hotel
1 bedroom, 2 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 5 reviews
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Featured hotel
Hotel in Summerland Key
Waterfront two bedroom cottage
1 bedroom, 2 king beds, 1 bathroom
14–19 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Home in Cudjoe Key
Jan. Disc, Waterfront Retreat/Dock/Pool/golf cart,
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 29 reviews
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Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds, 3 bathrooms
8–13 Jan
4.83 out of 5 average rating, 111 reviews
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Featured hotel
Room in Key West
Classic Double Queen City/Balcony
2 queen beds, 1 bathroom
19–24 Sept
4.8 out of 5 average rating, 69 reviews
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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, 209 reviews
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Guest favourite
Home in Cudjoe Key
Yellow Home - Receive $400 towards a Boat Rental!
3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.88 out of 5 average rating, 42 reviews
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Guest favourite
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 127 reviews
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Featured hotel
Room in Key West
Marker residences one bedroom suite
2 king beds, 1 bathroom
5–10 Sept
New place to stay
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Guest favourite
Home in Cudjoe Key
Waterfront Sanctuary in the Keys!
2 bedrooms, 2 beds, 2 bathrooms
31 Oct – 5 Nov
4.89 out of 5 average rating, 158 reviews