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

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Featured hotel
Hotel in Summerland Key
Parmer's Resort, King room
1 bedroom, 1 king bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 10 reviews
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Home in Big Pine Key
Your Perfect Florida Keys Escape
3 bedrooms, 3 beds, 2 bathrooms
9–14 Nov
New place to stay
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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
1–6 Oct
4.88 out of 5 average rating, 132 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
25–30 Oct
4.89 out of 5 average rating, 104 reviews
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Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 2 bathrooms
1–6 Oct
4.96 out of 5 average rating, 55 reviews
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Top guest favourite
Room in Big Pine Key
Old Island Life
1 queen bed, 1 bathroom
1–6 Oct
4.9 out of 5 average rating, 621 reviews
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Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4 bedrooms, 6 beds, 2 bathrooms
1–6 Oct
4.95 out of 5 average rating, 116 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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Flat in Big Pine Key
New Deluxe Duplex Unit, 2 Queen Beds, Unit G-4
2 bedrooms, 2 beds, 1 bathroom
2–7 Oct
4.79 out of 5 average rating, 106 reviews
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Guest favourite
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
2 bedrooms, 4 beds, 2 bathrooms
25–30 Nov
4.89 out of 5 average rating, 9 reviews
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Guest favourite
Home in Little Torch Key
Waterfront Beach Houses with Dock & Heated Pool!
8 bedrooms, 15 beds, 5 bathrooms
13–18 Oct
4.89 out of 5 average rating, 84 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 Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms, 2 beds, 2 bathrooms
7–12 Oct
5.0 out of 5 average rating, 51 reviews
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Guest favourite
Home in Cudjoe Key
Relaxing and Inviting home with 35' Private Dock
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Oct
4.85 out of 5 average rating, 61 reviews
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Featured hotel
Hotel in Key West
Silver Palms Inn & Historic Homes, Classic Double.
1 bedroom, 2 queen beds, 1 bathroom
5–10 Oct
4.81 out of 5 average rating, 79 reviews
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Home in Cudjoe Key
Private Secluded Ocean View & Pool Near Key West
4 bedrooms, 4 beds, 2 bathrooms
10–15 Oct
New place to stay
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Superhost
Home in Marathon
NEW! Reel Escape - 4br/No Stairs/Dock/Kayaks/Bikes
4 bedrooms, 7 beds, 3 bathrooms
10–17 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
1–6 Oct
4.97 out of 5 average rating, 37 reviews