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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
16–21 Aug
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4.75 out of 5 average rating, 157 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
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, 102 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
4.88 out of 5 average rating, 128 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
22–27 Aug
4.93 out of 5 average rating, 127 reviews
Guest favourite
Home in Big Pine Key
Cozy house with relaxing pool
2 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
4.8 out of 5 average rating, 10 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, 9 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
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 Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds, 2 bathrooms
24–29 Sept
4.97 out of 5 average rating, 206 reviews
Guest favourite
Boat in Key West
*August/September specials* off Grid Boat Key West
1 queen bed, 1 bathroom
12–17 Aug
4.96 out of 5 average rating, 91 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
18–23 Aug
4.91 out of 5 average rating, 557 reviews
Featured hotel
Hotel in Summerland Key
King room
1 bedroom, 1 king bed, 1 bathroom
8–13 Aug
5.0 out of 5 average rating, 9 reviews
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
4.93 out of 5 average rating, 74 reviews
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds, 3 bathrooms
25–30 Sept
5.0 out of 5 average rating, 14 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
Guest favourite
Cottage in Cudjoe Key
2Bd/1Ba Waterfront Retreat w/35’ Dock
2 bedrooms, 2 queen beds, 1 bathroom
31 Aug – 5 Sept
4.84 out of 5 average rating, 32 reviews
Home in Marathon
Casa Entera Frente al Mar + Muelle 50'
3 bedrooms, 4 beds, 2 bathrooms
8–15 Aug
New place to stay