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

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Superhost
Home in Upper Sugarloaf Key
Palm - Beach Houses Key West
2 bedrooms, 2 beds, 2 private bathrooms
9–14 Oct
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4.71 out of 5 average rating, 114 reviews
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Superhost
Tiny home in Summerland Key
Bungalow
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
4.82 out of 5 average rating, 95 reviews
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Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
4.94 out of 5 average rating, 82 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 Oct
4.97 out of 5 average rating, 37 reviews
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Guest favourite
Tiny home in Summerland Key
Waterview Bungalow
1 bedroom, 1 king bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 19 reviews
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Superhost
Apartment in Summerland Key
Standard Suite at Sugarloaf Key Hotel
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 6 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, 40 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
19–24 Oct
5.0 out of 5 average rating, 13 reviews
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Guest favourite
Home in Summerland Key
4BR Villa | Private Pool & Tiki | 30 Min to KW
4 bedrooms, 9 beds, 4 bathrooms
19–24 Oct
4.95 out of 5 average rating, 39 reviews
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Luxe
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
1–6 Oct
4.56 out of 5 average rating, 25 reviews
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Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 10 reviews
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Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds, 1 bathroom
3–8 Oct
4.73 out of 5 average rating, 37 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
26–31 Oct
5.0 out of 5 average rating, 19 reviews
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Featured hotel
Hotel in Key West
Havana 2 queens
1 bedroom, 2 queen beds, 1 bathroom
1–6 Oct
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Superhost
Home in Upper Sugarloaf Key
The Lighthouse - Beach Houses Key West
2 bedrooms, 1 sofa bed, 1 bathroom
1–6 Oct
4.93 out of 5 average rating, 134 reviews
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Guest favourite
Home in Cudjoe Key
Relaxing and Inviting home with 35' Private Dock
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Oct
4.85 out of 5 average rating, 61 reviews
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Guest favourite
Home in Cudjoe Key
Betty's Place
2 bedrooms, 3 beds, 2 bathrooms
5–10 Oct
4.92 out of 5 average rating, 122 reviews
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Guest favourite
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
1 bedroom, 3 beds, 1 bathroom
1–6 Oct
4.88 out of 5 average rating, 133 reviews
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Superhost
Home in Cudjoe Key
Oceanfront with 50’ Dock & Stunning Views
2 bedrooms, 5 beds, 2 bathrooms
12–17 Oct
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