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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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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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Superhost
Tiny home in Summerland Key
Bungalow
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.81 out of 5 average rating, 91 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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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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Superhost
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 209 reviews
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Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 47 reviews
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Guest favourite
Tiny home in Summerland Key
Waterview Bungalow
1 bedroom, 1 king bed, 1 bathroom
5–10 Sept
5.0 out of 5 average rating, 19 reviews
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Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
1 bedroom, 3 beds, 1 bathroom
30 Sept – 5 Oct
4.94 out of 5 average rating, 36 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
7–12 Sept
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Home in Cudjoe Key
Tiki Time in Cudjoe Key 136
2 bedrooms, 2 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 57 reviews
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Superhost
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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Featured hotel
Room in Key West
Ocean view one king bed accessible
1 bathroom
7–12 Sept
New place to stay
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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
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
2 bedrooms, 4 beds, 1 bathroom
1–6 Sept
4.89 out of 5 average rating, 184 reviews
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Guest favourite
Home in Cudjoe Key
Oceanside home 107,dock,kayaks,bikes,pool,fishing,
2 bedrooms, 3 beds, 3 bathrooms
7–12 Sept
4.94 out of 5 average rating, 34 reviews
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Top guest favourite
Home in Cudjoe Key
Rise And Shine On The Water
2 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
4.91 out of 5 average rating, 75 reviews
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Superhost
Home in Cudjoe Key
Blue Heaven Waterfront Home
2 bedrooms, 3 beds, 2 bathrooms
5–10 Sept
4.89 out of 5 average rating, 18 reviews
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Top guest favourite
Home in Cudjoe Key
Waterfront, Dock, Pool, Pickleball, near Key West!
2 bedrooms, 3 beds, 1 bathroom
6–11 Sept
4.99 out of 5 average rating, 74 reviews