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

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Home in Big Pine Key
Your Perfect Florida Keys Escape
3 bedrooms, 3 beds
18–23 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
19–24 Sept
4.88 out of 5 average rating, 132 reviews
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Guest favourite
Home in Big Pine Key
Cozy house with relaxing pool
2 bedrooms, 3 beds
28 Aug – 2 Sept
4.83 out of 5 average rating, 12 reviews
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Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds
20–25 Sept
4.89 out of 5 average rating, 104 reviews
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Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
3 bedrooms, 6 beds
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
18–23 Sept
4.95 out of 5 average rating, 116 reviews
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Top guest favourite
Room in Big Pine Key
Old Island Life
1 queen bed
18–23 Sept
4.9 out of 5 average rating, 621 reviews
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Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 16 reviews
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Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds
25–30 Sept
5.0 out of 5 average rating, 10 reviews
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Houseboat in Big Pine Key
1 Bedroom Floating Cabin # 9 Hammerhead
1 bedroom, 1 sofa bed
18–23 Sept
4.69 out of 5 average rating, 65 reviews
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Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom, 4 beds
19–24 Sept
4.97 out of 5 average rating, 37 reviews
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Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms, 2 beds
20–25 Sept
5.0 out of 5 average rating, 51 reviews
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Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds
16–21 Oct
4.96 out of 5 average rating, 212 reviews
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Flat in Big Pine Key
New Deluxe Duplex Unit, 2 Queen Beds, Unit G-4
2 bedrooms, 2 beds
27 Sept – 2 Oct
4.79 out of 5 average rating, 106 reviews
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Home in Cudjoe Key
Private Secluded Ocean View & Pool Near Key West
4 bedrooms, 4 beds
18–23 Sept
New place to stay
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Top guest favourite
Home in Cudjoe Key
Rise And Shine On The Water
2 bedrooms, 3 beds
19–24 Sept
4.91 out of 5 average rating, 75 reviews
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Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds
18–23 Sept
4.71 out of 5 average rating, 35 reviews
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Top guest favourite
Home in Marathon
Tropical Keys Retreat | Pool | Hot Tub | Cinema
3 bedrooms, 4 beds
20–27 Sept
5.0 out of 5 average rating, 81 reviews