filters

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

Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds, 4 bathrooms
5–10 Oct
4.91 out of 5 average rating, 101 reviews
Guest favourite
Home in Big Pine Key
Cozy house with relaxing pool
2 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
4.78 out of 5 average rating, 9 reviews
Guest favourite
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
1 bedroom, 3 beds, 1 bathroom
9–14 Aug
4.87 out of 5 average rating, 127 reviews
Guest favourite
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 1 bathroom
7–12 Sept
4.93 out of 5 average rating, 127 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, 14 reviews
Top guest favourite
Guest suite in Big Pine Key
Old Island Life
1 bedroom, 1 queen bed, 1 bathroom
11–16 Aug
4.89 out of 5 average rating, 619 reviews
Flat in Big Pine Key
New Deluxe Duplex Unit, 2 Queen Beds, Unit G-4
2 bedrooms, 2 beds, 1 bathroom
12–17 Sept
4.81 out of 5 average rating, 103 reviews
Home in Big Pine Key
Falcon’s Cove in Big Pine Key
2 bedrooms, 3 beds, 1.5 bathrooms
17–22 Aug
Home in Cudjoe Key
Heron House
2 bedrooms, 5 beds, 2 bathrooms
13–18 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Cudjoe Key
Waterfront Sanctuary in the Keys!
2 bedrooms, 2 beds, 2 bathrooms
1–6 Oct
4.89 out of 5 average rating, 157 reviews
Villa in Marathon
The Lucky Fisherman Retreat
4 bedrooms, 7 beds, 3 bathrooms
16–23 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Cudjoe Key
Yellow Home - Receive $400 towards a Boat Rental!
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.88 out of 5 average rating, 40 reviews
Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 44 reviews
Top guest favourite
Cottage in Cudjoe Key
King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
4.94 out of 5 average rating, 178 reviews
Guest favourite
Cottage in Cudjoe Key
2Bd/1Ba Waterfront Retreat w/35’ Dock
2 bedrooms, 2 queen beds, 1 bathroom
21–26 Aug
4.84 out of 5 average rating, 32 reviews
Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
1 bedroom, 3 beds, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 32 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
6–11 Aug
4.56 out of 5 average rating, 25 reviews
Guest favourite
Boat in Big Pine Key
2 Bedroom Aqua Lodge # 15 Porgie
1 bedroom, 2 beds, 1 bathroom
10–15 Aug
5.0 out of 5 average rating, 8 reviews