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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, 4 bathrooms
5–10 Oct
4.89 out of 5 average rating, 103 reviews
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Guest favourite
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 127 reviews
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Featured hotel
Hotel in Summerland Key
King room
1 bedroom, 1 king bed, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 10 reviews
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Home in Big Pine Key
Falcon’s Cove in Big Pine Key
2 bedrooms, 3 beds, 1.5 bathrooms
9–14 Sept
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Guest favourite
Home in Little Torch Key
Waterfront Beach Houses with Dock & Heated Pool!
8 bedrooms, 15 beds, 5 bathrooms
27 Sept – 2 Oct
4.89 out of 5 average rating, 84 reviews
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Flat in Big Pine Key
New Deluxe Duplex Unit, 2 Queen Beds, Unit G-4
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.81 out of 5 average rating, 104 reviews
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Top guest favourite
Guest suite in Big Pine Key
Old Island Life
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
4.9 out of 5 average rating, 620 reviews
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Top guest favourite
Home in Cudjoe Key
Keys Island Villa - Venture Out Home 354
2 bedrooms, 2 beds, 2 bathrooms
7–12 Sept
4.95 out of 5 average rating, 91 reviews
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Guest favourite
Home in Cudjoe Key
Yellow Home - Receive $400 towards a Boat Rental!
3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.88 out of 5 average rating, 42 reviews
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Guest favourite
Home in Cudjoe Key
Betty's Place
2 bedrooms, 3 beds, 2 bathrooms
18–23 Sept
4.92 out of 5 average rating, 119 reviews
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Top guest favourite
Home in Marathon
70ft Dock, Bikes, Beach, Spacious, VACA23-16
3 bedrooms, 5 beds, 3 bathrooms
13–20 Sept
4.94 out of 5 average rating, 205 reviews
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Guest favourite
Cottage in Cudjoe Key
Beautiful Cottage & Amenities in Gated Community
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.97 out of 5 average rating, 129 reviews
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Guest favourite
Home in Little Torch Key
Sterling Bay House
6 bedrooms, 8 beds, 6.5 bathrooms
12–19 Sept
5.0 out of 5 average rating, 5 reviews
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Superhost
Home in Cudjoe Key
Oceanfront w/ Dock, Swimming pool, Hot Tub, Kayaks
2 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
4.92 out of 5 average rating, 97 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, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 14 reviews
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Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds, 2 bathrooms
24–29 Oct
4.96 out of 5 average rating, 209 reviews
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Top guest favourite
Home in Marathon
Waterfront 6BR Luxury Retreat w/ Pool & Dock
6 bedrooms, 10 beds, 5 bathrooms
19–26 Sept
5.0 out of 5 average rating, 31 reviews
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Houseboat in Big Pine Key
1 Bedroom Floating Cabin # 9 Hammerhead
1 bedroom, 1 sofa bed, 1 bathroom
6–11 Sept
4.69 out of 5 average rating, 65 reviews