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Search results; Over 1,000 homes in Key West

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Guest favourite
Flat in Key West
Key West Beachside 1400sf, 2 Bedroom Condo
2 bedrooms, 2 beds, 2 private bathrooms
17–22 Sept
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4.9 out of 5 average rating, 168 reviews
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Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
4.91 out of 5 average rating, 562 reviews
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Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds, 1 bathroom
16–21 Sept
4.71 out of 5 average rating, 35 reviews
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Featured hotel
Hotel in Key West
Classic Double Queen City/Balcony
1 bedroom, 2 queen beds, 1 bathroom
3–8 Oct
4.8 out of 5 average rating, 75 reviews
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Guest favourite
Boat in Key West
Stay on Roxie - free transport & snacks, BYOB.
1 bedroom, 2 beds, 1 bathroom
19–24 Sept
4.9 out of 5 average rating, 245 reviews
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Top guest favourite
Apartment in Key West
Coastline Comfort
2 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 11 reviews
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Featured hotel
Hotel in Key West
Queen Room
1 bedroom, 1 queen bed, 1 bathroom
30 Oct – 4 Nov
4.95 out of 5 average rating, 19 reviews
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Guest favourite
Home in Key West
Waterlane House at Lunara Bay
4 bedrooms, 7 beds, 4.5 bathrooms
27 Sept – 2 Oct
4.85 out of 5 average rating, 112 reviews
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Guest favourite
Boat in Key West
*Off Grid Boat Key West
1 queen bed, 1 bathroom
16–21 Sept
4.96 out of 5 average rating, 95 reviews
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Top guest favourite
Houseboat in Marathon
b watervibe
1 bedroom, 1 small double bed, 1 bathroom
4–9 Oct
4.93 out of 5 average rating, 98 reviews
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Guest favourite
Boat in Key West
Sailboat Retreat | Resort Amenities
1 bedroom, 1 queen bed, 2 bathrooms
27 Sept – 2 Oct
4.93 out of 5 average rating, 56 reviews
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Top guest favourite
Home in Key West
Casa Cristol - Truman Annex
3 bedrooms, 3 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 23 reviews
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Superhost
Houseboat in Key West
Amazing houseboat with 2nd floor observation deck
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
4.89 out of 5 average rating, 180 reviews
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Top guest favourite
Home in Key West
Luxury Retreat-Old Town; Pool, Parking, Near Duval
2 bedrooms, 4 beds, 2.5 bathrooms
5–10 Oct
5.0 out of 5 average rating, 13 reviews
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Guest favourite
Boat in Key West
Waterfront Boat Stay + Resort Amenities
1 bedroom, 2 beds, 1 bathroom
26 Sept – 1 Oct
4.94 out of 5 average rating, 36 reviews
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Featured hotel
Hotel in Key West
Two bedrooms bi-level garden view suite
2 bedrooms, 1 bathroom
25–30 Sept
4.8 out of 5 average rating, 25 reviews
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Guest favourite
Boat in Key West
“The Easy Way” Comfy, Practical, Convenient
1 bedroom, 1 king bed, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 24 reviews
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Top guest favourite
Boutique hotel in Key West
Mallory House Room #3
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.89 out of 5 average rating, 528 reviews
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Top guest favourite
Boat in Key West
All Inclusive! Snorkel • Sail • Sun & Fun
3 bedrooms, 3 queen beds, 2.5 bathrooms
17–22 Sept
4.88 out of 5 average rating, 177 reviews