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

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Houseboat in Big Pine Key
2 Bedroom Aqualodge # 1 Mahi
2 bedrooms, 3 beds, 1 private bathroom
1–6 Oct
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4.58 out of 5 average rating, 106 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
1–6 Oct
4.88 out of 5 average rating, 133 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
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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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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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
Anchor House
4 bedrooms, 7 beds, 2 bathrooms
1–6 Oct
4.95 out of 5 average rating, 116 reviews
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Guest favourite
Home in Summerland Key
Captain House
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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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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Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Home in Marathon
Tropical Keys Retreat | Pool | Hot Tub | Cinema
3 bedrooms, 4 beds, 3 bathrooms
1–8 Oct
5.0 out of 5 average rating, 81 reviews
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Top guest favourite
Home in Marathon
70ft Dock, Bikes, Beach, Spacious, VACA23-16
3 bedrooms, 5 beds, 3 bathrooms
30 Nov – 7 Dec
4.94 out of 5 average rating, 206 reviews
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Guest favourite
Home in Little Torch Key
Barry Beach & Guesthouse
8 bedrooms, 15 beds, 5 bathrooms
13–18 Oct
4.89 out of 5 average rating, 84 reviews
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Guest favourite
Home in Cudjoe Key
Cozy 2 br/2 bath home in Cudjoe
2 bedrooms, 3 beds, 2 bathrooms
11–16 Oct
4.88 out of 5 average rating, 91 reviews
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Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds, 1 bathroom
3–8 Oct
4.73 out of 5 average rating, 37 reviews
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Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds, 3 bathrooms
2–7 Nov
4.83 out of 5 average rating, 112 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
1–6 Oct
4.95 out of 5 average rating, 92 reviews
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Top guest favourite
Camper van/Motorhome in Big Pine Key
Perfect Couple Oasis!
1 bedroom, 1 bed, 1 bathroom
1–6 Oct
4.96 out of 5 average rating, 27 reviews