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Search results; Over 1,000 homes in Big Pine Key

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Home in Big Pine Key
The Hideaway - Private Paradise at its Best!
3 bedrooms, 4 beds, 2 private bathrooms
20–25 Sept
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4.51 out of 5 average rating, 138 reviews
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Guest favourite
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
1 bedroom, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.88 out of 5 average rating, 132 reviews
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Home in Big Pine Key
Your Perfect Florida Keys Escape
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
New place to stay
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Guest favourite
Home in Big Pine Key
Cozy house with relaxing pool
2 bedrooms, 3 beds, 2 bathrooms
14–19 Nov
4.83 out of 5 average rating, 12 reviews
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Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds, 4 bathrooms
20–25 Sept
4.89 out of 5 average rating, 104 reviews
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Top guest favourite
Room in Big Pine Key
Old Island Life
1 queen bed, 1 bathroom
21–26 Sept
4.9 out of 5 average rating, 621 reviews
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Guest favourite
Flat in Big Pine Key
New Deluxe Duplex Unit, 1 Queen Bed, Unit E-2
1 bedroom, 1 bed, 1 bathroom
23–28 Sept
4.92 out of 5 average rating, 24 reviews
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Home in Big Pine Key
Pool-3 BR 2 BR-Water Front with a Fixed bridge
3 bedrooms, 7 beds, 2 bathrooms
1–8 Oct
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Top guest favourite
Home in Summerland Key
Ocean front classic keys cottage
3 bedrooms, 5 beds, 2 bathrooms
8–15 Dec
4.95 out of 5 average rating, 20 reviews
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Guest favourite
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 1 bathroom
12–17 Oct
4.93 out of 5 average rating, 127 reviews
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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, 16 reviews
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Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
21–26 Sept
4.94 out of 5 average rating, 82 reviews
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Superhost
Home in Marathon
NEW! Reel Escape - 4br/No Stairs/Dock/Kayaks/Bikes
4 bedrooms, 7 beds, 3 bathrooms
3–10 Oct
New place to stay
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Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom, 4 beds, 1 bathroom
21–26 Sept
4.97 out of 5 average rating, 37 reviews
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Flat in Big Pine Key
New Deluxe Duplex Unit, 2 Queen Beds, Unit J-7
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.89 out of 5 average rating, 70 reviews
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Superhost
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
2 bedrooms, 4 beds, 1 bathroom
11–16 Oct
4.89 out of 5 average rating, 185 reviews
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Top guest favourite
Home in Cudjoe Key
Keys Island Villa - Venture Out Home 354
2 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 92 reviews
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Guest favourite
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
2 bedrooms, 4 beds, 2 bathrooms
1–6 Dec
4.89 out of 5 average rating, 9 reviews
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Guest favourite
Home in Cudjoe Key
Heron House at Venture Out Resort
2 bedrooms, 5 beds, 2 bathrooms
13–18 Oct
5.0 out of 5 average rating, 8 reviews