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

Top guest favourite
Guest suite in Big Pine Key
Old Island Life
1 bedroom, 1 queen bed
4–9 Aug
4.89 out of 5 average rating, 619 reviews
Guest favourite
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
1 bedroom, 3 beds
9–14 Aug
4.87 out of 5 average rating, 127 reviews
Guest favourite
Boat in Big Pine Key
2 Bedroom Aqua Lodge # 15 Porgie
1 bedroom, 2 beds
10–15 Aug
5.0 out of 5 average rating, 8 reviews
Flat in Big Pine Key
New Deluxe Duplex Unit, 2 Queen Beds, Unit J-7
2 bedrooms, 2 beds
16–21 Aug
4.88 out of 5 average rating, 69 reviews
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds
5–10 Oct
4.91 out of 5 average rating, 101 reviews
Featured hotel
Hotel in Summerland Key
King room
1 bedroom, 1 king bed
8–13 Aug
5.0 out of 5 average rating, 9 reviews
Featured hotel
Room in Key West
One king bed
9–14 Aug
New place to stay
Top guest favourite
Home in Cudjoe Key
Keys Island Villa - Venture Out Home 354
2 bedrooms, 2 beds
4–9 Aug
4.94 out of 5 average rating, 89 reviews
Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms, 2 beds
23–28 Aug
5.0 out of 5 average rating, 43 reviews
Guest favourite
Home in Big Pine Key
Cozy house with relaxing pool
2 bedrooms, 3 beds
15–20 Nov
4.78 out of 5 average rating, 9 reviews
Home in Big Pine Key
Falcon’s Cove in Big Pine Key
2 bedrooms, 3 beds
11–16 Aug
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
3 bedrooms, 6 beds
8–13 Aug
4.96 out of 5 average rating, 54 reviews
Superhost
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
2 bedrooms, 4 beds
12–17 Aug
4.89 out of 5 average rating, 183 reviews
Guest favourite
Flat in Big Pine Key
New Deluxe Duplex Unit, 1 Queen Bed, Unit E-2
1 bedroom, 1 bed
29 Aug – 3 Sept
4.92 out of 5 average rating, 24 reviews
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4 bedrooms, 6 beds
8–13 Aug
4.95 out of 5 average rating, 115 reviews
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds
20–25 Sept
5.0 out of 5 average rating, 14 reviews
Room in Key West
*Near Mallory Square | Resort Pool, Dining + Bar
1 king bed
2–7 Oct
4.67 out of 5 average rating, 6 reviews
Superhost
Home in Big Pine Key
Twin Palms Canal Front
2 bedrooms, 3 beds
1–6 Mar