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

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Top guest favourite
Camper van/Motorhome in Big Pine Key
Perfect Couple Oasis!
1 bedroom, 1 bed, 1 private bathroom
19–24 Sept
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4.96 out of 5 average rating, 27 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
19–24 Sept
4.88 out of 5 average rating, 132 reviews
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Home in Big Pine Key
Your Perfect Florida Keys Escape
3 bedrooms, 3 beds, 2 bathrooms
18–23 Sept
New place to stay
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Guest favourite
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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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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Top guest favourite
Room in Big Pine Key
Old Island Life
1 queen bed, 1 bathroom
18–23 Sept
4.9 out of 5 average rating, 621 reviews
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Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 2 bathrooms
18–23 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
18–23 Sept
4.95 out of 5 average rating, 116 reviews
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Guest favourite
Flat in Big Pine Key
New Deluxe Duplex Unit, 1 Queen Bed, Unit E-2
1 bedroom, 1 bed, 1 bathroom
23–28 Sept
4.92 out of 5 average rating, 24 reviews
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Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 82 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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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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Home in Big Pine Key
Perfect getaway
3 bedrooms, 6 beds, 3 bathrooms
19–24 Sept
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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, 51 reviews
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Superhost
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
2 bedrooms, 4 beds, 1 bathroom
18–23 Sept
4.89 out of 5 average rating, 185 reviews
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Superhost
Home in Cudjoe Key
Oceanfront w/ Dock, Swimming pool, Hot Tub, Kayaks
2 bedrooms, 4 beds, 2 bathrooms
19–24 Sept
4.92 out of 5 average rating, 98 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
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Guest favourite
Home in Little Torch Key
Sterling Bay House
6 bedrooms, 8 beds, 6.5 bathrooms
20–27 Sept
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Home in Cudjoe Key
Waterfront Sanctuary in the Keys!
2 bedrooms, 2 beds, 2 bathrooms
29 Nov – 4 Dec
4.88 out of 5 average rating, 161 reviews