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

Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
4.91 out of 5 average rating, 99 reviews, 3 bedrooms, 3 beds, 4 bathrooms
5–10 Oct
Guest favourite
Home in Big Pine Key
Cozy house with relaxing pool
4.78 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
Superhost
Home in Big Pine Key
Private Island - The true privilege of seclusion
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
7–14 Aug
Guest favourite
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp!
4.93 out of 5 average rating, 125 reviews, 3 bedrooms, 6 beds, 1 bathroom
22–27 Aug
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4.56 out of 5 average rating, 25 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Aug
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5.0 out of 5 average rating, 38 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
29 Aug – 5 Sept
Superhost
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
4.87 out of 5 average rating, 125 reviews, 1 bedroom, 3 beds, 1 bathroom
9–14 Aug
Guest favourite
Home in Little Torch Key
Sterling Bay House
5.0 out of 5 average rating, 5 reviews, 6 bedrooms, 8 beds, 6.5 bathrooms
8–15 Aug
Flat in Big Pine Key
New Deluxe Duplex Unit, 2 Queen Beds, Unit H-5
4.94 out of 5 average rating, 64 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Guest favourite
Home in Marathon
Beach House in Marathon with Amazing Backyard!
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 4 beds, 2 bathrooms
9–16 Aug
Top guest favourite
Guest suite in Big Pine Key
Old Island Life
4.89 out of 5 average rating, 616 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
5.0 out of 5 average rating, 41 reviews, 2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug
Home in Big Pine Key
Falcon’s Cove in Big Pine Key
2 bedrooms, 3 beds, 1.5 bathrooms
11–16 Aug
Guest favourite
Home in Marathon
Soothing Nest
4.85 out of 5 average rating, 34 reviews, 3 bedrooms, 5 beds, 2 bathrooms
15–20 Sept
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
5.0 out of 5 average rating, 85 reviews, 4 bedrooms, 8 beds, 3 bathrooms
15–22 Aug
Guest favourite
Home in Cudjoe Key
Betty's Place
4.91 out of 5 average rating, 116 reviews, 2 bedrooms, 3 beds, 2 bathrooms
14–19 Aug
Top guest favourite
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 4 beds, 2 bathrooms
24–29 Aug