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

Home in Big Pine Key
Your Perfect Florida Keys Escape
3 bedrooms, 3 beds
12–17 Sept
New place to stay
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
Guest favourite
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
1 bedroom, 3 beds
12–17 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
11–16 Sept
4.9 out of 5 average rating, 620 reviews
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
Houseboat in Big Pine Key
1 Bedroom Floating Cabin # 9 Hammerhead
1 bedroom, 1 sofa bed
11–16 Sept
4.69 out of 5 average rating, 65 reviews
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
Home in Big Pine Key
Tampa/Ruskin Waterfront Escape
2 bedrooms, 3 beds
15–20 Sept
New place to stay
Superhost
Home in Big Pine Key
Big Pine Key Vacation home
3 bedrooms, 3 beds
29 Nov – 4 Dec
4.9 out of 5 average rating, 10 reviews
Home in Big Pine Key
Falcon’s Cove in Big Pine Key
2 bedrooms, 3 beds
11–16 Sept
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, 105 reviews
Guest favourite
Home in Cudjoe Key
Yellow Home - Receive $400 towards a Boat Rental!
3 bedrooms, 3 beds
13–18 Sept
4.88 out of 5 average rating, 43 reviews
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds
12–17 Sept
4.94 out of 5 average rating, 81 reviews
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, 49 reviews
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
Top guest favourite
Cottage in Cudjoe Key
King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!
2 bedrooms, 3 beds
6–11 Oct
4.94 out of 5 average rating, 180 reviews
Featured hotel
Hotel in Summerland Key
King room
1 bedroom, 1 king bed
11–16 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Little Torch Key
Sterling Bay House
6 bedrooms, 8 beds
13–20 Sept
5.0 out of 5 average rating, 5 reviews