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

Featured hotel
Hotel in Summerland Key
King room
1 bedroom, 1 king bed, 1 bathroom
9–14 Sept
5.0 out of 5 average rating, 10 reviews
Home in Big Pine Key
Your Perfect Florida Keys Escape
3 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
New place to stay
Guest favourite
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
1 bedroom, 3 beds, 1 bathroom
9–14 Sept
4.88 out of 5 average rating, 132 reviews
Top guest favourite
Guest suite in Big Pine Key
Old Island Life
1 bedroom, 1 queen bed, 1 bathroom
9–14 Sept
4.9 out of 5 average rating, 620 reviews
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
Superhost
Home in Big Pine Key
Big Pine Key Vacation home
3 bedrooms, 3 beds, 2 bathrooms
29 Nov – 4 Dec
4.9 out of 5 average rating, 10 reviews
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4 bedrooms, 6 beds, 2 bathrooms
16–21 Sept
4.95 out of 5 average rating, 116 reviews
Guest favourite
Home in Cudjoe Key
Heron House at Venture Out Resort
2 bedrooms, 5 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
2 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
4.88 out of 5 average rating, 8 reviews
Guest favourite
Home in Cudjoe Key
Blue Heaven Waterfront Home
2 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
4.89 out of 5 average rating, 18 reviews
Featured hotel
Room in Marathon
Three bedroom beachfront villa
4 king beds, 1 bathroom
9–14 Sept
New place to stay
Top guest favourite
Home in Cudjoe Key
Ocean's Edge VO Pad Boards, Kayak, Bikes-30 min KW
2 bedrooms, 4 beds, 1 bathroom
18–23 Oct
4.97 out of 5 average rating, 95 reviews
Guest favourite
Home in Cudjoe Key
Betty's Place
2 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.92 out of 5 average rating, 120 reviews
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
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
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 2 bathrooms
14–19 Sept
4.96 out of 5 average rating, 55 reviews
Featured hotel
Room in Key West
Classic Double Queen City/Balcony
2 queen beds, 1 bathroom
9–14 Sept
4.81 out of 5 average rating, 72 reviews
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
10–15 Sept
4.94 out of 5 average rating, 81 reviews