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

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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 private bathroom
8–13 Sept
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4.88 out of 5 average rating, 130 reviews
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Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds
5–10 Oct
4.89 out of 5 average rating, 103 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
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp!
3 bedrooms, 6 beds
13–18 Sept
4.93 out of 5 average rating, 127 reviews
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Home in Big Pine Key
Falcon’s Cove in Big Pine Key
2 bedrooms, 3 beds
9–14 Sept
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Top guest favourite
Guest suite in Big Pine Key
Old Island Life
1 bedroom, 1 queen bed
7–12 Sept
4.9 out of 5 average rating, 620 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
4.81 out of 5 average rating, 104 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, 15 reviews
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Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds
24–29 Oct
4.96 out of 5 average rating, 209 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
20–25 Sept
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Home in Marathon
70ft Dock, Bikes, Beach, Spacious, VACA23-16
3 bedrooms, 5 beds
13–20 Sept
4.94 out of 5 average rating, 205 reviews
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Superhost
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
2 bedrooms, 4 beds
1–6 Sept
4.89 out of 5 average rating, 184 reviews
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Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds
6–11 Sept
4.86 out of 5 average rating, 28 reviews
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Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom, 4 beds
1–6 Sept
4.97 out of 5 average rating, 36 reviews
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Guest favourite
Home in Cudjoe Key
Heron House at Venture Out Resort
2 bedrooms, 5 beds
5–10 Sept
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 8 reviews
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Superhost
Home in Big Pine Key
Twin Palms Canal Front
2 bedrooms, 3 beds
1–6 Mar
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Top guest favourite
Home in Marathon
Waterfront 6BR Luxury Retreat w/ Pool & Dock
6 bedrooms, 10 beds
19–26 Sept
5.0 out of 5 average rating, 31 reviews
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Guest favourite
Home in Marathon
Florida Keys Retreat /Game Room / Boat Parking
2 bedrooms, 3 beds
19–26 Sept
4.82 out of 5 average rating, 56 reviews