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

Guest favourite
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
1 bedroom, 3 beds, 1 bathroom
16–21 Aug
4.88 out of 5 average rating, 129 reviews
Top guest favourite
Guest suite in Big Pine Key
Old Island Life
1 bedroom, 1 queen bed, 1 bathroom
14–19 Aug
4.89 out of 5 average rating, 619 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
4.91 out of 5 average rating, 102 reviews
Home in Big Pine Key
Falcon’s Cove in Big Pine Key
2 bedrooms, 3 beds, 1.5 bathrooms
17–22 Aug
Guest favourite
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 1 bathroom
22–27 Aug
4.93 out of 5 average rating, 127 reviews
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
4.94 out of 5 average rating, 78 reviews
Guest favourite
Boat in Big Pine Key
2 Bedroom Aqua Lodge # 15 Porgie
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 8 reviews
Superhost
Tiny home in Summerland Key
Bungalow
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.8 out of 5 average rating, 85 reviews
Guest favourite
Home in Cudjoe Key
Waterfront Sanctuary in the Keys!
2 bedrooms, 2 beds, 2 bathrooms
12–17 Oct
4.89 out of 5 average rating, 157 reviews
Flat in Big Pine Key
New Deluxe Duplex Unit, 2 Queen Beds, Unit J-7
2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
4.88 out of 5 average rating, 69 reviews
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds, 2 bathrooms
24–29 Sept
4.97 out of 5 average rating, 206 reviews
Top guest favourite
Cottage in Cudjoe Key
King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
4.94 out of 5 average rating, 179 reviews
Guest favourite
Boat in Key West
*August/September specials* off Grid Boat Key West
1 queen bed, 1 bathroom
14–19 Aug
4.96 out of 5 average rating, 92 reviews
Guest favourite
Boat in Key West
“The Easy Way” Comfy, Practical, Convenient
1 bedroom, 1 king bed, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 24 reviews
Guest favourite
Boat in Key West
Stay on Roxie - free transport & snacks, BYOB.
1 bedroom, 2 beds, 1 bathroom
1–6 Sept
4.9 out of 5 average rating, 245 reviews
Guest favourite
Home in Big Pine Key
Cozy house with relaxing pool
2 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
4.82 out of 5 average rating, 11 reviews
Top guest favourite
Guest suite in Key Colony Beach
Turtle-By-The-Sea: the Best Deal in KCB!
1 bedroom, 1 queen bed, 1 bathroom
22–29 Aug
4.99 out of 5 average rating, 140 reviews
Top guest favourite
Home in Marathon
Cozy home with dock & direct Atlantic access
1 bedroom, 1 bathroom
1–6 Jan
5.0 out of 5 average rating, 6 reviews