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

Houseboat in Big Pine Key
2-Bedroom Aqualodge # 11 Grouper
2 bedrooms, 3 beds, 1 private bathroom
13–18 Aug
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4.75 out of 5 average rating, 155 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, 97 reviews
Guest favourite
Home in Big Pine Key
Cozy house with relaxing pool
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.78 out of 5 average rating, 9 reviews
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
4.96 out of 5 average rating, 53 reviews
Top guest favourite
Guest suite in Big Pine Key
Old Island Life
1 bedroom, 1 queen bed, 1 bathroom
19–24 Jul
4.89 out of 5 average rating, 615 reviews
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
4.95 out of 5 average rating, 114 reviews
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Cabin in Big Pine Key
2 Bedroom Yellow Cabin
2 bedrooms, 3 beds, 1 bathroom
7–12 Aug
4.71 out of 5 average rating, 110 reviews
Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
1 bedroom, 3 beds, 1 bathroom
24–29 Jul
4.97 out of 5 average rating, 30 reviews
Superhost
Home in Little Torch Key
New House on Little Torch Key
3 bedrooms, 6 beds, 2 bathrooms
19–26 Jul
Guest favourite
Home in Cudjoe Key
Blue Palms Retreat
3 bedrooms, 4 beds, 2 bathrooms
1–8 Aug
4.94 out of 5 average rating, 18 reviews
Guest favourite
Home in Marathon
Soothing Nest
3 bedrooms, 5 beds, 2 bathrooms
15–20 Sept
4.84 out of 5 average rating, 32 reviews
Guest favourite
Home in Cudjoe Key
Yellow Home - Receive $400 towards a Boat Rental!
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.87 out of 5 average rating, 39 reviews
Top guest favourite
Home in Cudjoe Key
Aug. Discount, Waterfront Retreat/Pool/golf cart
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 27 reviews
Superhost
Home in Big Pine Key
Florida Keys Retreat
2 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
New place to stay
Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 40 reviews
Superhost
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
1 bedroom, 3 beds, 1 bathroom
9–14 Aug
4.87 out of 5 average rating, 124 reviews
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
4.97 out of 5 average rating, 201 reviews