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Search results; Over 1,000 homes in Summerland Key

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Home in Summerland Key
Kelly’s Kabin - Private FL Keys Cottage
1 bedroom, 3 beds, 1 private bathroom
7–12 Sept
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4.77 out of 5 average rating, 92 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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Featured hotel
Room in Key West
Classic Double Queen City/Balcony
2 queen beds, 1 bathroom
13–18 Sept
4.8 out of 5 average rating, 69 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
Bungalow
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.82 out of 5 average rating, 92 reviews
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Featured hotel
Room in Key West
Ocean view one king bed
1 bathroom
6–11 Sept
4.88 out of 5 average rating, 8 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
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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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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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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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
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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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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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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Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 15 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
4.97 out of 5 average rating, 58 reviews
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Guest favourite
Home in Big Pine Key
Cozy house with relaxing pool
2 bedrooms, 3 beds, 2 bathrooms
14–19 Nov
4.83 out of 5 average rating, 12 reviews
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Home in Cudjoe Key
NEW Listing•Solace by the Sea•37’Dock•Ocean Views
2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
New place to stay