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Search results; Over 1,000 homes in Key West

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Top guest favourite
Apartment in Key West
Gorgeous Ocean View in Paradise, Close to Key West
3 bedrooms, 4 beds, 2 shared bathrooms
3–8 Oct
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4.99 out of 5 average rating, 140 reviews
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Top guest favourite
Home in Key West
Casa Calypso 3bed3bath sleeps 8 beautiful decorate
3 bedrooms, 5 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 41 reviews
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Guest favourite
Home in Key West
Waterlane House at Lunara Bay
4 bedrooms, 7 beds
27 Sept – 2 Oct
4.85 out of 5 average rating, 112 reviews
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Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds
20–25 Sept
4.71 out of 5 average rating, 35 reviews
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Superhost
Home in Marathon
NEW! Reel Escape - 4br/No Stairs/Dock/Kayaks/Bikes
4 bedrooms, 7 beds
3–10 Oct
New place to stay
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Guest favourite
Home in Key West
Cathouse Old Town Oasis Huge Heated Pool & Parking
4 bedrooms, 7 beds
22–27 Sept
4.98 out of 5 average rating, 80 reviews
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Top guest favourite
Flat in Key West
The Perch on Duval- Hip & Modern Duval Suite
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 118 reviews
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Superhost
Apartment in Key West
Key West Paradise Condo w/ Pool, Hot Tub, Tennis
2 bedrooms, 3 beds
22–27 Sept
New place to stay
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Hotel in Key West
*Near Mallory Square | Resort Pool, Dining + Bar
1 bedroom, 1 king bed
20–25 Sept
4.73 out of 5 average rating, 26 reviews
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Guest favourite
Apartment in Key West
Penthouse Waterfront Dock Pool Condo Near Duval St
4 bedrooms, 11 beds
13–18 Oct
4.9 out of 5 average rating, 265 reviews
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Boat in Key West
Serenova - 58' Leopard Catamaran
3 bedrooms, 3 queen beds
25–30 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Key West
Paradise found
3 bedrooms, 4 beds
29 Sept – 4 Oct
4.94 out of 5 average rating, 159 reviews
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Top guest favourite
Home in Marathon
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
4 bedrooms, 4 beds
3–10 Oct
5.0 out of 5 average rating, 6 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, 212 reviews
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Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds
25–30 Sept
5.0 out of 5 average rating, 10 reviews
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Guest favourite
Apartment in Key West
Waterfront Dock Pool Near Duval St Penthouse
4 bedrooms, 9 beds
4–9 Oct
4.92 out of 5 average rating, 218 reviews
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Superhost
Apartment in Key West
The Tahiti Suite | Updated Key West Condo w/ Pool!
2 bedrooms, 3 beds
26 Sept – 1 Oct
New place to stay
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Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed
27 Sept – 2 Oct
4.91 out of 5 average rating, 562 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