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Search results; Over 1,000 homes in Key West

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Guest favourite
Boat in Key West
Stay on Roxie - free transport & snacks, BYOB.
1 bedroom, 2 beds, 1 private bathroom
7–12 Sept
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4.9 out of 5 average rating, 245 reviews
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Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds, 1 bathroom
13–18 Sept
4.83 out of 5 average rating, 24 reviews
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Guest favourite
Home in Key West
Gone Coastal 2
3 bedrooms, 5 beds, 2.5 bathrooms
25–30 Sept
4.93 out of 5 average rating, 126 reviews
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Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
2–7 Sept
4.91 out of 5 average rating, 559 reviews
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Guest favourite
Apartment in Key West
Penthouse Waterfront Dock Pool Condo Near Duval St
4 bedrooms, 11 beds, 4 bathrooms
4–9 Oct
4.9 out of 5 average rating, 264 reviews
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Guest favourite
Flat in Key West
Castaway Cove: Pet-friendly 2/2 condo near beach!
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
4.89 out of 5 average rating, 119 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
20–25 Sept
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Apartment in Key West
Coastline Comfort
2 bedrooms, 4 beds, 2 bathrooms
22–27 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Key West
Casa Calypso 3bed3bath sleeps 8 beautiful decorate
3 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 39 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
7–12 Sept
4.81 out of 5 average rating, 26 reviews
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Featured hotel
Room in Key West
La Pensione Inn Adults Only- Deluxe King
1 king bed, 1 bathroom
7–12 Sept
4.8 out of 5 average rating, 10 reviews
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Guest favourite
Home in Key West
MERMAID COVE- Funky Getaway on Duval
4 bedrooms, 5 beds, 4 bathrooms
22–27 Sept
4.9 out of 5 average rating, 250 reviews
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Guest favourite
Apartment in Key West
EYW Getaway
2 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
4.99 out of 5 average rating, 86 reviews
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Guest favourite
Apartment in Key West
Waterfront Dock Pool Near Duval St Penthouse
4 bedrooms, 9 beds, 4 bathrooms
1–6 Sept
4.92 out of 5 average rating, 214 reviews
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Luxe
Home in Key West
The Dreamside House at Lunara Bay
8 bedrooms, 8 king beds, 8.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Casa particular in Key West
Amazing Canal front home in KW!
4 bedrooms, 5 beds, 3 bathrooms
9–14 Sept
5.0 out of 5 average rating, 41 reviews
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Top guest favourite
Apartment in Key West
Waterfront Condo | Pool, Dock, Parking, Sleeps 8
2 bedrooms, 4 beds, 2 bathrooms
3–8 Sept
4.87 out of 5 average rating, 302 reviews
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Superhost
Boat in Key West
Waterfront & Heated Pool - Away Awai Floating Vill
2 bedrooms, 2 queen beds, 2 bathrooms
8–13 Sept
4.93 out of 5 average rating, 86 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
8–13 Sept
5.0 out of 5 average rating, 19 reviews