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Search results; Over 1,000 homes in Key West

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Guest favourite
Apartment in Key West
Henry's Piece of Paradise On The Ocean In Key West
2 bedrooms, 3 beds, 2 bathrooms
26 Sept – 1 Oct
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4.85 out of 5 average rating, 40 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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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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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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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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Top guest favourite
Apartment in Key West
Waterfront Condo Dock Pool Near Duval St
2 bedrooms, 4 beds, 2 bathrooms
9–14 Oct
4.9 out of 5 average rating, 157 reviews
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Guest favourite
Home in Key West
Cathouse Old Town Oasis Huge Heated Pool & Parking
4 bedrooms, 7 beds, 2.5 bathrooms
22–27 Sept
4.98 out of 5 average rating, 80 reviews
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Guest favourite
Home in Key West
Slice of Paradise
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
4.92 out of 5 average rating, 25 reviews
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Superhost
Home in Key West
Poolside Paradise
3 bedrooms, 6 beds, 3 bathrooms
11–16 Oct
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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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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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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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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
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 22 reviews
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Top guest favourite
Flat in Key West
Duval Balcony - Suite Mischief
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
4.88 out of 5 average rating, 814 reviews
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Guest favourite
Tiny home in Key West
Downtown Studio half block from Duval w parking
1 bed, 1 bathroom
26 Sept – 1 Oct
4.86 out of 5 average rating, 480 reviews
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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
Home in Key West
Pilar House
3 bedrooms, 3 beds, 2 bathrooms
13–18 Dec
4.96 out of 5 average rating, 47 reviews
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Guest favourite
Flat in Key West
Duval Balcony - Street Suite
1 king bed, 1 bathroom
11–16 Oct
4.84 out of 5 average rating, 899 reviews