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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, 97 reviews, 3 bedrooms, 3 beds, 4 bathrooms
22–27 Aug
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
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
5.0 out of 5 average rating, 12 reviews, 4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
4.96 out of 5 average rating, 52 reviews, 3 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
Superhost
Home in Marathon
*NEW!*Life is a Marathon~VIEWS!~Pool~Dock~HotTub!
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
16–23 Jul
Top guest favourite
Guest suite in Big Pine Key
Old Island Life
4.89 out of 5 average rating, 615 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Jul
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4.95 out of 5 average rating, 114 reviews, 4 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
4.97 out of 5 average rating, 201 reviews, 2 bedrooms, 3 beds, 2 bathrooms
22–27 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, 124 reviews, 1 bedroom, 3 beds, 1 bathroom
9–14 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
17–22 Jul
Superhost
Home in Key West
Poolside Paradise
New place to stay, 3 bedrooms, 6 beds, 3 bathrooms
15–20 Aug
Top guest favourite
Home in Cudjoe Key
Aug. Discount, Waterfront Retreat/Pool/golf cart
4.96 out of 5 average rating, 27 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Home in Marathon
4BR Gulffront Dog Friendly | Pool | Dock | Deck
4.71 out of 5 average rating, 7 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
16–23 Aug
Superhost
Home in Little Torch Key
New House on Little Torch Key
3 bedrooms, 6 beds, 2 bathrooms
17–24 Jul
Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
4.97 out of 5 average rating, 30 reviews, 1 bedroom, 3 beds, 1 bathroom
24–29 Jul
Guest favourite
Home in Cudjoe Key
Blue Palms Retreat
4.94 out of 5 average rating, 18 reviews, 3 bedrooms, 4 beds, 2 bathrooms
1–8 Aug
Top guest favourite
Home in Marathon
NEW! Private Pool, 50’ Dock, Kayaks, Waterfront
4.97 out of 5 average rating, 35 reviews, 3 bedrooms, 2.5 bathrooms
15–22 Sept