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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 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
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
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
9–14 Aug
4.56 out of 5 average rating, 25 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
9–14 Aug
4.88 out of 5 average rating, 128 reviews
Home in Marathon
Casa Entera Frente al Mar + Muelle 50'
3 bedrooms, 4 beds, 2 bathrooms
8–15 Aug
New place to stay
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, 41 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
Guest favourite
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
2 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
5.0 out of 5 average rating, 6 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, 86 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, 38 reviews
Guest favourite
Home in Marathon
New oceanfront 5BR home w/pool, slip, and beach
5 bedrooms, 8 beds, 4 bathrooms
16–23 Aug
4.95 out of 5 average rating, 22 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
Guest favourite
Cottage in Cudjoe Key
Beautiful Cottage & Amenities in Gated Community
2 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
4.97 out of 5 average rating, 128 reviews
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
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
Top guest favourite
Home in Marathon
Oceanfront•Sunrise•5BR Pool &Hot Tub•Walk to Beach
5 bedrooms, 10 beds, 6 bathrooms
15–22 Aug
5.0 out of 5 average rating, 16 reviews