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Search results; Over 1,000 homes in Key West

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Guest favourite
Apartment in Key West
Key Wes't Best- Upgraded condo 5 mins to Smathers
2 bedrooms, 3 beds, 2 private bathrooms
8–13 Oct
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4.89 out of 5 average rating, 108 reviews
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Featured hotel
Hotel in Key West
Havana Cabana at Key West, Havana 2 queens
1 bedroom, 2 queen beds
1–6 Oct
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Featured hotel
Hotel in Key West
Seashell Motel, Queen Room
1 bedroom, 1 queen bed
9–14 Oct
5.0 out of 5 average rating, 20 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
17–22 Oct
5.0 out of 5 average rating, 18 reviews
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Guest favourite
Home in Key West
Gone Coastal 2
3 bedrooms, 5 beds
18–23 Oct
4.93 out of 5 average rating, 130 reviews
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Superhost
Home in Key West
Poolside Paradise
3 bedrooms, 6 beds
11–16 Oct
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Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed
14–19 Oct
4.91 out of 5 average rating, 562 reviews
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Featured hotel
Hotel in Key West
Havana Cabana at Key West, Havana king accessible
1 bedroom, 1 king bed
1–6 Oct
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Superhost
Home in Marathon
NEW! Reel Escape - 4br/No Stairs/Dock/Kayaks/Bikes
4 bedrooms, 7 beds
10–17 Oct
New place to stay
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Guest favourite
Flat in Key West
Castaway Cove: Pet-friendly 2/2 condo near beach!
2 bedrooms, 3 beds
1–6 Oct
4.89 out of 5 average rating, 123 reviews
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Top guest favourite
Home in Key West
Casa Calypso 3bed3bath sleeps 8 beautiful decorate
3 bedrooms, 5 beds
1–6 Oct
5.0 out of 5 average rating, 41 reviews
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Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds
16–21 Oct
4.96 out of 5 average rating, 213 reviews
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Top guest favourite
Apartment in Key West
Waterfront Condo Dock Pool Near Duval St
2 bedrooms, 4 beds
9–14 Oct
4.9 out of 5 average rating, 158 reviews
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Guest favourite
Home in Key West
Cathouse Old Town Oasis Huge Heated Pool & Parking
4 bedrooms, 7 beds
11–16 Oct
4.98 out of 5 average rating, 80 reviews
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Hotel in Key West
*Near Mallory Square | Resort Pool, Dining + Bar
1 bedroom, 1 king bed
1–6 Oct
4.69 out of 5 average rating, 29 reviews
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Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds
3–8 Oct
4.73 out of 5 average rating, 37 reviews
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Guest favourite
Room in Key West
Mallory House Room #2
1 queen bed
1–6 Oct
4.91 out of 5 average rating, 443 reviews
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Luxe
Home in Key West
Altair House at Lunara Bay
6 bedrooms, 9 beds
26–31 Oct
4.87 out of 5 average rating, 45 reviews
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Guest favourite
Hotel room in Key West
The Sanchez House Room #1
1 bedroom, 1 queen bed
1–6 Oct
4.86 out of 5 average rating, 673 reviews