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Search results; Over 1,000 homes in Key West

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Guest favourite
Home in Key West
Key West Paradise
3 bedrooms, 5 beds, 3 private bathrooms
7–12 Sept
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4.89 out of 5 average rating, 99 reviews
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Top guest favourite
Apartment in Key West
Boat Slip - Waterfront Condo - Key West Pool
2 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 7 reviews
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Boat in Key West
Serenova - 58' Leopard Catamaran
3 bedrooms, 3 queen beds
14–19 Sept
New place to stay
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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
20–25 Sept
5.0 out of 5 average rating, 14 reviews
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Guest favourite
Boat in Key West
“The Easy Way” Comfy, Practical, Convenient
1 bedroom, 1 king bed
8–13 Sept
5.0 out of 5 average rating, 24 reviews
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Guest favourite
Home in Key West
Casa Calypso 3bed3bath sleeps 8 beautiful decorate
3 bedrooms, 5 beds
14–19 Sept
5.0 out of 5 average rating, 39 reviews
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Top guest favourite
Apartment in Key West
Coastline Comfort
2 bedrooms, 4 beds
22–27 Sept
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Casa particular in Key West
Amazing Canal front home in KW!
4 bedrooms, 5 beds
9–14 Sept
5.0 out of 5 average rating, 41 reviews
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Guest favourite
Boat in Key West
3BR In Resort Village, Pools, Free Kayak & Shuttle
3 bedrooms, 3 beds
7–12 Sept
4.81 out of 5 average rating, 27 reviews
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Guest favourite
Home in Key West
Paradise found
3 bedrooms, 4 beds
7–12 Sept
4.94 out of 5 average rating, 157 reviews
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Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds
6–11 Sept
4.86 out of 5 average rating, 29 reviews
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Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds
8–13 Sept
5.0 out of 5 average rating, 20 reviews
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Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed
13–18 Sept
4.91 out of 5 average rating, 561 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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Guest favourite
Home in Key West
MERMAID COVE- Funky Getaway on Duval
4 bedrooms, 5 beds
22–27 Sept
4.9 out of 5 average rating, 250 reviews
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Guest favourite
Home in Key West
Thompson Island USA !! Your Key West Retreat !!
9 bedrooms, 10 king beds
6–11 Sept
4.79 out of 5 average rating, 105 reviews
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Guest favourite
Flat in Key West
Castaway Cove: Pet-friendly 2/2 condo near beach!
2 bedrooms, 3 beds
28 Sept – 3 Oct
4.89 out of 5 average rating, 120 reviews
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Superhost
Home in Marathon
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
4 bedrooms, 4 beds
5–12 Sept
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Home in Key West
Real World MTV House Key West - 18 to 22 guests
10 bedrooms, 13 beds
2–7 Sept
4.86 out of 5 average rating, 125 reviews