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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, 157 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, 101 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 Anchor House with Boat Basin & Ramp!
4 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
4.95 out of 5 average rating, 115 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, 54 reviews
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 Aug
4.87 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
11–16 Aug
Flat in Big Pine Key
New Deluxe Duplex Unit, 2 Queen Beds, Unit J-7
2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 68 reviews
Villa in Marathon
The Lucky Fisherman Retreat
4 bedrooms, 7 beds, 3 bathrooms
18–25 Aug
5.0 out of 5 average rating, 4 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, 14 reviews
Top guest favourite
Guest suite in Big Pine Key
Old Island Life
1 bedroom, 1 queen bed, 1 bathroom
2–7 Aug
4.89 out of 5 average rating, 618 reviews
Guest favourite
Home in Cudjoe Key
Waterfront Sanctuary in the Keys!
2 bedrooms, 2 beds, 2 bathrooms
1–6 Oct
4.89 out of 5 average rating, 157 reviews
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
4 bedrooms, 8 beds, 3 bathrooms
22–29 Aug
5.0 out of 5 average rating, 86 reviews
Top guest favourite
Home in Marathon
Fishing, 70ft Dock, Bikes, Beach VACA23-16
3 bedrooms, 5 beds, 3 bathrooms
23–30 Aug
4.94 out of 5 average rating, 203 reviews
Home in Summerland Key
Paraiso
3 bedrooms, 2 beds, 2 bathrooms
14–19 Aug
Guest favourite
Home in Cudjoe Key
Yellow Home - Receive $400 towards a Boat Rental!
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.88 out of 5 average rating, 40 reviews
Guest favourite
Home in Cudjoe Key
Blue Heaven Waterfront Home
2 bedrooms, 3 beds, 2 bathrooms
15–22 Aug
4.89 out of 5 average rating, 18 reviews
Guest favourite
Home in Marathon
Soothing Nest
3 bedrooms, 5 beds, 2 bathrooms
17–22 Oct
4.85 out of 5 average rating, 34 reviews
Guest favourite
Home in Marathon
Beach House in Marathon with Amazing Backyard!
2 bedrooms, 4 beds, 2 bathrooms
9–16 Aug
5.0 out of 5 average rating, 10 reviews