filters

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

Photo 1 of 6
Guest favourite
Tiny home in Big Pine Key
Tiny House | 35 min to KW + Free Parking & Pool
2 bedrooms, 4 beds, 1 private bathroom
25–30 Sept
,
4.8 out of 5 average rating, 270 reviews
Photo 1 of 6
Guest favourite
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
1 bedroom, 3 beds, 1 bathroom
8–13 Sept
4.88 out of 5 average rating, 130 reviews
Photo 1 of 6
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
Photo 1 of 6
Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom, 4 beds, 1 bathroom
1–6 Sept
4.97 out of 5 average rating, 36 reviews
Photo 1 of 6
Guest favourite
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 127 reviews
Photo 1 of 6
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
Photo 1 of 6
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
Photo 1 of 6
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
Photo 1 of 6
Home in Big Pine Key
Your Perfect Florida Keys Escape
3 bedrooms, 3 beds, 2 bathrooms
9–14 Nov
New place to stay
Photo 1 of 6
Guest favourite
Home in Cudjoe Key
Blue Heaven Waterfront Home
2 bedrooms, 3 beds, 2 bathrooms
5–10 Sept
4.89 out of 5 average rating, 18 reviews
Photo 1 of 6
Top guest favourite
Home in Marathon
Waterfront Cozy Modern Retreat w/Deep Canal
2 bedrooms, 3 beds, 1 bathroom
26 Sept – 3 Oct
4.9 out of 5 average rating, 190 reviews
Photo 1 of 6
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, 209 reviews
Photo 1 of 6
Featured hotel
Hotel in Summerland Key
King room
1 bedroom, 1 king bed, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 10 reviews
Photo 1 of 6
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
4.94 out of 5 average rating, 80 reviews
Photo 1 of 6
Superhost
Home in Cudjoe Key
Oceanfront w/ Dock, Swimming pool, Hot Tub, Kayaks
2 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
4.92 out of 5 average rating, 97 reviews
Photo 1 of 6
Top guest favourite
Cottage in Cudjoe Key
King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!
2 bedrooms, 3 beds, 2 bathrooms
6–11 Oct
4.94 out of 5 average rating, 180 reviews
Photo 1 of 6
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, 151 reviews
Photo 1 of 6
Top guest favourite
Home in Summerland Key
Ocean front classic keys cottage
3 bedrooms, 5 beds, 2 bathrooms
1–8 Nov
4.95 out of 5 average rating, 20 reviews
Photo 1 of 6
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, 8 reviews