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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
9–14 Sept
4.88 out of 5 average rating, 132 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
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
Home in Big Pine Key
Your Perfect Florida Keys Escape
3 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
New place to stay
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 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 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
Home in Big Pine Key
Falcon’s Cove in Big Pine Key
2 bedrooms, 3 beds, 1.5 bathrooms
9–14 Sept
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
4.79 out of 5 average rating, 105 reviews
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 16 reviews
Guest favourite
Flat in Big Pine Key
New Deluxe Duplex Unit, 1 Queen Bed, Unit E-2
1 bedroom, 1 bed, 1 bathroom
17–22 Sept
4.92 out of 5 average rating, 24 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 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
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
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
Top guest favourite
Home in Key Colony Beach
Captain’s Quarters Ahoy Mateys! Florida, Keys
2 bedrooms, 2 beds, 2 bathrooms
13–18 Sept
4.93 out of 5 average rating, 153 reviews
Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 48 reviews
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, 211 reviews