filters

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
20–25 Sept
,
4.75 out of 5 average rating, 157 reviews
Home in Big Pine Key
Your Perfect Florida Keys Escape
3 bedrooms, 3 beds, 2 bathrooms
15–20 Sept
New place to stay
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
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
1 bedroom, 3 beds, 1 bathroom
15–20 Sept
4.88 out of 5 average rating, 132 reviews
Featured hotel
Hotel in Summerland Key
King room
1 bedroom, 1 king bed, 1 bathroom
17–22 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 2 bathrooms
15–20 Sept
4.96 out of 5 average rating, 55 reviews
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4 bedrooms, 6 beds, 2 bathrooms
16–21 Sept
4.95 out of 5 average rating, 116 reviews
Top guest favourite
Guest suite in Big Pine Key
Old Island Life
1 bedroom, 1 queen bed, 1 bathroom
16–21 Sept
4.9 out of 5 average rating, 621 reviews
Houseboat in Big Pine Key
1 Bedroom Floating Cabin # 9 Hammerhead
1 bedroom, 1 sofa bed, 1 bathroom
15–20 Sept
4.69 out of 5 average rating, 65 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, 16 reviews
Home in Big Pine Key
Falcon’s Cove in Big Pine Key
2 bedrooms, 3 beds, 1.5 bathrooms
15–20 Sept
Guest favourite
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
2 bedrooms, 4 beds, 2 bathrooms
1–6 Dec
4.88 out of 5 average rating, 8 reviews
Guest favourite
Home in Summerland Key
4BR Villa | Private Pool & Tiki | 30 Min to KW
4 bedrooms, 9 beds, 4 bathrooms
25–30 Oct
4.95 out of 5 average rating, 39 reviews
Home in Cudjoe Key
Private Secluded Ocean View & Pool Near Key West
4 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
New place to stay
Guest favourite
Home in Little Torch Key
Sterling Bay House
6 bedrooms, 8 beds, 6.5 bathrooms
17–24 Sept
5.0 out of 5 average rating, 5 reviews
Flat in Big Pine Key
New Deluxe Duplex Unit, 2 Queen Beds, Unit J-7
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.89 out of 5 average rating, 70 reviews
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 10 reviews
Superhost
Home in Marathon
Waterfront Pool Home w/ Private Dock, Tiki Hut & B
4 bedrooms, 7 beds, 2 bathrooms
28 Nov – 5 Dec
5.0 out of 5 average rating, 3 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, 212 reviews