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

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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 private bathroom
1–6 Oct
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4.92 out of 5 average rating, 24 reviews
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Home in Big Pine Key
Your Perfect Florida Keys Escape
3 bedrooms, 3 beds
9–14 Nov
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
1–6 Oct
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
14–19 Nov
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
25–30 Oct
4.89 out of 5 average rating, 104 reviews
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Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4 bedrooms, 6 beds
1–6 Oct
4.95 out of 5 average rating, 116 reviews
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Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
3 bedrooms, 6 beds
1–6 Oct
4.96 out of 5 average rating, 55 reviews
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Top guest favourite
Room in Big Pine Key
Old Island Life
1 queen bed
1–6 Oct
4.9 out of 5 average rating, 621 reviews
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Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds
1–6 Oct
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Home in Marathon
Tropical Keys Retreat | Pool | Hot Tub | Cinema
3 bedrooms, 4 beds
1–8 Oct
5.0 out of 5 average rating, 81 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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Top guest favourite
Home in Summerland Key
Ocean front classic keys cottage
3 bedrooms, 5 beds
8–15 Dec
4.95 out of 5 average rating, 20 reviews
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Guest favourite
Home in Cudjoe Key
Cozy 2 br/2 bath home in Cudjoe
2 bedrooms, 3 beds
11–16 Oct
4.88 out of 5 average rating, 91 reviews
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Top guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds
17–22 Oct
5.0 out of 5 average rating, 18 reviews
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Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds
13–18 Oct
5.0 out of 5 average rating, 16 reviews
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Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds
3–8 Oct
4.71 out of 5 average rating, 35 reviews
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Home in Big Pine Key
Pool-3 BR 2 BR-Water Front with a Fixed bridge
3 bedrooms, 7 beds
1–8 Oct
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Superhost
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
2 bedrooms, 4 beds
11–16 Oct
4.89 out of 5 average rating, 185 reviews
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Guest favourite
Home in Cudjoe Key
Waterfront Sanctuary in the Keys!
2 bedrooms, 2 beds
29 Nov – 4 Dec
4.88 out of 5 average rating, 162 reviews