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Search results; Over 1,000 homes in Big Pine Key

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Featured hotel
Hotel in Key West
Classic Double Queen City/Balcony
1 bedroom, 2 queen beds, 1 bathroom
3–8 Oct
4.8 out of 5 average rating, 75 reviews
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Featured hotel
Hotel in Summerland Key
King room
1 bedroom, 1 king bed, 1 bathroom
17–22 Sept
5.0 out of 5 average rating, 10 reviews
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Home in Big Pine Key
Your Perfect Florida Keys Escape
3 bedrooms, 3 beds, 2 bathrooms
17–22 Sept
New place to stay
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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
19–24 Sept
4.88 out of 5 average rating, 132 reviews
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Superhost
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds, 4 bathrooms
20–25 Sept
4.89 out of 5 average rating, 104 reviews
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Featured hotel
Hotel in Key West
Havana king room
1 bedroom, 2 king beds, 1 bathroom
17–22 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Guest suite in Big Pine Key
Old Island Life
1 bedroom, 1 queen bed, 1 bathroom
17–22 Sept
4.9 out of 5 average rating, 621 reviews
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Houseboat in Big Pine Key
1 Bedroom Floating Cabin # 9 Hammerhead
1 bedroom, 1 sofa bed, 1 bathroom
17–22 Sept
4.69 out of 5 average rating, 65 reviews
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Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
18–23 Sept
4.94 out of 5 average rating, 81 reviews
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Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 2 bathrooms
17–22 Sept
4.96 out of 5 average rating, 55 reviews
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Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4 bedrooms, 6 beds, 2 bathrooms
17–22 Sept
4.95 out of 5 average rating, 116 reviews
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Top guest favourite
Camper van/Motorhome in Big Pine Key
Perfect Couple Oasis!
1 bedroom, 1 bed, 1 bathroom
18–23 Sept
4.96 out of 5 average rating, 27 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, 16 reviews
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Guest favourite
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
2 bedrooms, 4 beds, 2 bathrooms
1–6 Dec
4.88 out of 5 average rating, 8 reviews
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Superhost
Home in Big Pine Key
Big Pine Key Vacation home
3 bedrooms, 3 beds, 2 bathrooms
29 Nov – 4 Dec
4.9 out of 5 average rating, 10 reviews
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Top guest favourite
Home in Cudjoe Key
Rise And Shine On The Water
2 bedrooms, 3 beds, 2 bathrooms
18–23 Sept
4.91 out of 5 average rating, 75 reviews
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Guest favourite
Home in Cudjoe Key
Blue Heaven Waterfront Home
2 bedrooms, 3 beds, 2 bathrooms
26 Sept – 1 Oct
4.89 out of 5 average rating, 18 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
19–24 Sept
4.97 out of 5 average rating, 37 reviews