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

Guest favourite
Tiny home in Big Pine Key
Tiny House | 35 min to KW + Free Parking & Pool
2 bedrooms, 4 beds, 1 private bathroom
25–30 Sept
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4.8 out of 5 average rating, 270 reviews
Guest favourite
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
1 bedroom, 3 beds, 1 bathroom
8–13 Sept
4.88 out of 5 average rating, 131 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 Summerland Key
Waterfront Haven House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 127 reviews
Home in Big Pine Key
Falcon’s Cove in Big Pine Key
2 bedrooms, 3 beds, 1.5 bathrooms
9–14 Sept
Top guest favourite
Guest suite in Big Pine Key
Old Island Life
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
4.9 out of 5 average rating, 620 reviews
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
4.81 out of 5 average rating, 104 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, 15 reviews
Top guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Cottage in Cudjoe Key
Beautiful Cottage & Amenities in Gated Community
2 bedrooms, 3 beds, 2 bathrooms
11–16 Sept
4.97 out of 5 average rating, 129 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, 210 reviews
Top guest favourite
Home in Marathon
70ft Dock, Bikes, Beach, Spacious, VACA23-16
3 bedrooms, 5 beds, 3 bathrooms
13–20 Sept
4.94 out of 5 average rating, 205 reviews
Top guest favourite
Home in Summerland Key
Ocean front classic keys cottage
3 bedrooms, 5 beds, 2 bathrooms
1–8 Nov
4.95 out of 5 average rating, 20 reviews
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
3–8 Sept
4.94 out of 5 average rating, 80 reviews
Guest favourite
Home in Cudjoe Key
Relaxing Home in the Keys
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.88 out of 5 average rating, 58 reviews
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Cudjoe Key
Heron House at Venture Out Resort
2 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Little Torch Key
Sterling Bay House
6 bedrooms, 8 beds, 6.5 bathrooms
12–19 Sept
5.0 out of 5 average rating, 5 reviews
Superhost
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
2 bedrooms, 4 beds, 1 bathroom
14–19 Sept
4.89 out of 5 average rating, 184 reviews