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

Guest favourite
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
1 bedroom, 3 beds, 1 private bathroom
8–13 Sept
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4.88 out of 5 average rating, 132 reviews
Home in Big Pine Key
Your Perfect Florida Keys Escape
3 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
New place to stay
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
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 Anchor House with Boat Basin & Ramp!
4 bedrooms, 6 beds, 2 bathrooms
7–12 Sept
4.95 out of 5 average rating, 116 reviews
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 2 bathrooms
14–19 Sept
4.96 out of 5 average rating, 55 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 Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 48 reviews
Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom, 4 beds, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 36 reviews
Home in Cudjoe Key
NEW Listing•Solace by the Sea•37’Dock•Ocean Views
2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
New place to stay
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 Cudjoe Key
Blue Heaven Waterfront Home
2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.89 out of 5 average rating, 18 reviews
Guest favourite
Home in Cudjoe Key
Yellow Home - Receive $400 towards a Boat Rental!
3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.88 out of 5 average rating, 42 reviews
Top guest favourite
Home in Key Colony Beach
Captain’s Quarters Ahoy Mateys! Florida, Keys
2 bedrooms, 2 beds, 2 bathrooms
13–18 Sept
4.93 out of 5 average rating, 152 reviews
Top guest favourite
Home in Marathon
Luxury Waterfront Home - Marathon, FL Keys - 5BR
5 bedrooms, 6 beds, 4 bathrooms
12–19 Sept
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Marathon
NEW!The Hideaway~Pool~Pickleball~Putt-Putt~Kayaks!
3 bedrooms, 4 beds, 2 bathrooms
12–19 Sept
4.92 out of 5 average rating, 84 reviews
Guest favourite
Home in Cudjoe Key
103- Newly Renovated House with Oceanview and Pool
2 bedrooms, 2 king beds, 3 bathrooms
7–12 Sept
5.0 out of 5 average rating, 16 reviews
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 9 reviews
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
4.94 out of 5 average rating, 81 reviews