filters

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

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
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
Top guest favourite
Home in Cudjoe Key
Waterfront, Dock, Pool, Pickleball, near Key West!
2 bedrooms, 3 beds, 1 bathroom
11–16 Sept
4.99 out of 5 average rating, 74 reviews
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds, 1 bathroom
31 Jul – 5 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms, 2 beds, 2 bathrooms
14–19 Aug
5.0 out of 5 average rating, 38 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 Cudjoe Key
Blue Heaven Waterfront Home
2 bedrooms, 3 beds, 2 bathrooms
15–22 Aug
4.88 out of 5 average rating, 17 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
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
4.95 out of 5 average rating, 63 reviews
Top guest favourite
Flat in Marathon
Waterfront Escape | Pool, Tiki, Breakfast & Marina
1 bedroom, 2 beds, 1 bathroom
15–20 Jul
5.0 out of 5 average rating, 22 reviews
Featured hotel
Hotel in Summerland Key
Waterfront two bedroom cottage
1 bedroom, 2 king beds, 1 bathroom
12–17 Jul
Top guest favourite
Home in Marathon
Tropical Keys Retreat | Pool | Hot Tub | Cinema
3 bedrooms, 4 beds, 3 bathrooms
18–25 Jul
5.0 out of 5 average rating, 76 reviews
Guest favourite
Cottage in Cudjoe Key
2Bd/1Ba Waterfront Retreat w/35’ Dock
2 bedrooms, 2 queen beds, 1 bathroom
12–17 Aug
4.83 out of 5 average rating, 30 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, 113 reviews
Top guest favourite
Cottage in Cudjoe Key
King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!
2 bedrooms, 3 beds, 2 bathrooms
28 Aug – 2 Sept
4.94 out of 5 average rating, 175 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 Cudjoe Key
Relaxing Home in the Keys
2 bedrooms, 2 beds, 1 bathroom
10–15 Aug
4.88 out of 5 average rating, 56 reviews
Superhost
Home in Marathon
Blue Heaven Marathon
3 bedrooms, 6 beds, 2 bathrooms
19–24 Jul