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

Superhost
Home in Big Pine Key
Oceanfront 360’ dock, tiki hut-dogs OK for a fee
3 bedrooms, 3 beds, 2 private bathrooms
18–23 Jul
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4.83 out of 5 average rating, 29 reviews
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds, 4 bathrooms
22–27 Aug
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
4.75 out of 5 average rating, 8 reviews
Guest favourite
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 1 bathroom
22–27 Aug
4.93 out of 5 average rating, 123 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
4.88 out of 5 average rating, 122 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
Top guest favourite
Guest suite in Big Pine Key
Old Island Life
1 bedroom, 1 queen bed, 1 bathroom
14–19 Jul
4.89 out of 5 average rating, 612 reviews
Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds, 1 bathroom
24–29 Aug
New place to stay
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
Flat in Big Pine Key
New Deluxe Duplex Unit, 2 Queen Beds, Unit G-4
2 bedrooms, 2 beds, 1 bathroom
22–27 Aug
4.8 out of 5 average rating, 102 reviews
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
4.97 out of 5 average rating, 201 reviews
Superhost
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds, 2 bathrooms
3–8 Aug
5.0 out of 5 average rating, 4 reviews
Home in Big Pine Key
Falcon’s Cove in Big Pine Key
2 bedrooms, 3 beds, 1.5 bathrooms
11–16 Aug
Guest favourite
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
4.92 out of 5 average rating, 64 reviews
Top guest favourite
Camper van/Motorhome in Big Pine Key
Perfect Couple Oasis!
1 bedroom, 1 bed, 1 bathroom
12–17 Jul
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Home in Cudjoe Key
Keys Island Villa - Venture Out Home 354
2 bedrooms, 2 beds, 2 bathrooms
25–30 Jul
4.94 out of 5 average rating, 84 reviews
Superhost
Tiny home in Big Pine Key
Tiny Fish Haus
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Jul
4.89 out of 5 average rating, 105 reviews
Superhost
Home in Little Torch Key
New House on Little Torch Key
3 bedrooms, 6 beds, 2 bathrooms
12–19 Jul
Featured hotel
Hotel in Summerland Key
Waterfront two bedroom cottage
1 bedroom, 2 king beds, 1 bathroom
12–17 Jul