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Search results; Over 1,000 homes in Key West

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Top guest favourite
Apartment in Key West
Waterfront Condo | Pool, Dock, Parking, Sleeps 8
2 bedrooms, 4 beds, 2 private bathrooms
8–13 Oct
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4.87 out of 5 average rating, 307 reviews
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Hotel in Key West
*Near Mallory Square | Resort Pool, Dining + Bar
1 bedroom, 1 king bed, 1 bathroom
19–24 Sept
4.73 out of 5 average rating, 26 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
20–25 Sept
4.81 out of 5 average rating, 79 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
20–25 Sept
4.71 out of 5 average rating, 35 reviews
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Guest favourite
Boat in Key West
3BR In Resort Village, Pools, Free Kayak & Shuttle
3 bedrooms, 3 beds, 2 bathrooms
2–7 Oct
4.83 out of 5 average rating, 30 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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Top guest favourite
Boat in Key West
All Inclusive! Snorkel • Sail • Sun & Fun
3 bedrooms, 3 queen beds, 2.5 bathrooms
20–25 Sept
4.88 out of 5 average rating, 177 reviews
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Top guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds, 2 bathrooms
17–22 Oct
5.0 out of 5 average rating, 18 reviews
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Top guest favourite
Apartment in Key West
Boat Slip - Waterfront Condo - Key West Pool
2 bedrooms, 4 beds, 2 bathrooms
7–12 Oct
5.0 out of 5 average rating, 9 reviews
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Featured hotel
Hotel in Key West
Santa Maria Suites, Two bedroom bi-level pool vie.
2 bedrooms, 1 bathroom
19–24 Sept
4.9 out of 5 average rating, 41 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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Guest favourite
Boat in Key West
*Off Grid Boat Key West
1 queen bed, 1 bathroom
19–24 Sept
4.96 out of 5 average rating, 95 reviews
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Superhost
Boat in Key West
Houseboat in Key West
1 bedroom, 1 bed, 1 bathroom
28 Sept – 3 Oct
4.85 out of 5 average rating, 74 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 Key West
Fully renovated 2/2 bath condo w/ shared pool!
2 bedrooms, 3 beds, 2 bathrooms
26 Sept – 1 Oct
4.95 out of 5 average rating, 212 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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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
Home in Key West
Paradise found
3 bedrooms, 4 beds, 3 bathrooms
29 Sept – 4 Oct
4.94 out of 5 average rating, 159 reviews