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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
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
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
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
1 bedroom, 3 beds, 1 bathroom
10–15 Aug
4.88 out of 5 average rating, 129 reviews
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 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
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
4 bedrooms, 8 beds, 3 bathrooms
22–29 Aug
5.0 out of 5 average rating, 87 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
11–16 Aug
4.56 out of 5 average rating, 25 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, 104 reviews
Top guest favourite
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
Superhost
Home in Marathon
*NEW* Reel Escape~Dock!~Lift!~Pet Friendly~Grill!
3 bedrooms, 3 beds, 2 bathrooms
22–29 Aug
New place to stay
Guest favourite
Home in Marathon
4BR 3B, Heated Pool & Spa, 60' Dock
4 bedrooms, 7 beds, 3 bathrooms
15–22 Aug
4.95 out of 5 average rating, 108 reviews
Home in Cudjoe Key
Heron House
2 bedrooms, 5 beds, 2 bathrooms
13–18 Aug
5.0 out of 5 average rating, 4 reviews
Home in Big Pine Key
Falcon’s Cove in Big Pine Key
2 bedrooms, 3 beds, 1.5 bathrooms
17–22 Aug
Top guest favourite
Home in Marathon
70ft Dock, Bikes, Beach, Spacious, VACA23-16
3 bedrooms, 5 beds, 3 bathrooms
23–30 Aug
4.94 out of 5 average rating, 203 reviews
Guest favourite
Home in Little Torch Key
Sterling Bay House
6 bedrooms, 8 beds, 6.5 bathrooms
12–19 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5 bedrooms, 7 beds, 3.5 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 39 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
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, 10 reviews