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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
13–18 Aug
,
4.75 out of 5 average rating, 155 reviews
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
4.97 out of 5 average rating, 201 reviews, 2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
Top guest favourite
Guest suite in Big Pine Key
Old Island Life
4.89 out of 5 average rating, 615 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Jul
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
4.91 out of 5 average rating, 97 reviews, 3 bedrooms, 3 beds, 4 bathrooms
22–27 Aug
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 4 beds, 1 bathroom
15–20 Aug
Guest favourite
Home in Big Pine Key
Cozy house with relaxing pool
4.78 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
Top guest favourite
Home in Cudjoe Key
Waterfront, Dock, Pool, Pickleball, near Key West!
4.99 out of 5 average rating, 74 reviews, 2 bedrooms, 3 beds, 1 bathroom
31 Aug – 5 Sept
Guest favourite
Home in Cudjoe Key
Blue Heaven Waterfront Home
4.88 out of 5 average rating, 17 reviews, 2 bedrooms, 3 beds, 2 bathrooms
15–22 Aug
Featured hotel
Hotel in Summerland Key
Waterfront two bedroom cottage
1 bedroom, 1 bathroom
10–15 Aug
Superhost
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
4.87 out of 5 average rating, 124 reviews, 1 bedroom, 3 beds, 1 bathroom
9–14 Aug
Top guest favourite
Home in Cudjoe Key
Rise And Shine On The Water
4.91 out of 5 average rating, 69 reviews, 2 bedrooms, 3 beds, 2 bathrooms
7–12 Aug
Top guest favourite
Cottage in Cudjoe Key
King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!
4.94 out of 5 average rating, 175 reviews, 2 bedrooms, 3 beds, 2 bathrooms
28 Aug – 2 Sept
Superhost
Home in Cudjoe Key
Ocean~View w/ Dock, Pool, Kayaks, King Bed
4.92 out of 5 average rating, 92 reviews, 2 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Marathon
Sombrero beach vacation paradise, great location
4.98 out of 5 average rating, 84 reviews, 3 bedrooms, 7 beds, 2 bathrooms
17–24 Aug
Guest favourite
Holiday home in Marathon
Cabana Club Condo: Key Colony Beach, FL
4.93 out of 5 average rating, 55 reviews, 2 bedrooms, 6 beds, 2 bathrooms
18–25 Jul
Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
4.97 out of 5 average rating, 33 reviews, 1 bedroom, 4 beds, 1 bathroom
16–21 Jul
Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
5.0 out of 5 average rating, 40 reviews, 2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug
Superhost
Home in Marathon
Blue Heaven Marathon
3 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Home in Marathon
Spacious, 70ft Dock, Bikes, Beach VACA23-16
4.95 out of 5 average rating, 202 reviews, 3 bedrooms, 5 beds, 3 bathrooms
15–22 Aug