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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
11–16 Aug
4.89 out of 5 average rating, 619 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 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
Home in Big Pine Key
Falcon’s Cove in Big Pine Key
2 bedrooms, 3 beds, 1.5 bathrooms
17–22 Aug
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
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
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
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 8 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
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
4.93 out of 5 average rating, 73 reviews
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds, 1 bathroom
30 Oct – 4 Nov
4.92 out of 5 average rating, 13 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
Superhost
Tiny home in Summerland Key
Bungalow
1 bedroom, 2 beds, 1 bathroom
15–20 Aug
4.79 out of 5 average rating, 82 reviews
Guest favourite
Boat in Key West
Stay on Roxie - free transport & snacks, BYOB.
1 bedroom, 2 beds, 1 bathroom
1–6 Sept
4.9 out of 5 average rating, 243 reviews
Home in Cudjoe Key
Heron House
2 bedrooms, 5 beds, 2 bathrooms
13–18 Aug
5.0 out of 5 average rating, 3 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
Featured hotel
Room in Key West
One queen bed
1 bathroom
7–12 Aug
New place to stay
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
6–11 Aug
4.91 out of 5 average rating, 557 reviews