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Search results; Over 1,000 homes in Key West

Flat in Key West
At Mine | Lovely Suite steps from Duval Street
1 bedroom, 1 bed, 1 private bathroom
18–23 Sept
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4.86 out of 5 average rating, 1741 reviews
Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds, 1 bathroom
15–20 Sept
4.71 out of 5 average rating, 35 reviews
Boat in Key West
Serenova - 58' Leopard Catamaran
3 bedrooms, 3 queen beds, 2 bathrooms
25–30 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Boat in Key West
3BR In Resort Village, Pools, Free Kayak & Shuttle
3 bedrooms, 3 beds, 2 bathrooms
2–7 Oct
4.81 out of 5 average rating, 27 reviews
Top guest favourite
Home in Key West
Casa Calypso 3bed3bath sleeps 8 beautiful decorate
3 bedrooms, 5 beds, 3 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Apartment in Key West
Waterfront Condo Dock Pool Near Duval St
2 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.9 out of 5 average rating, 156 reviews
Top guest favourite
Boat in Key West
All Inclusive! Snorkel • Sail • Sun & Fun
3 bedrooms, 3 queen beds, 2.5 bathrooms
17–22 Sept
4.88 out of 5 average rating, 177 reviews
Hotel in Key West
*Near Mallory Square | Resort Pool, Dining + Bar
1 bedroom, 1 king bed, 1 bathroom
15–20 Sept
4.72 out of 5 average rating, 25 reviews
Guest favourite
Boat in Key West
Waterfront Boat Stay + Resort Amenities
1 bedroom, 2 beds, 1 bathroom
26 Sept – 1 Oct
4.94 out of 5 average rating, 36 reviews
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 10 reviews
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
Featured hotel
Hotel in Key West
Queen Room
1 bedroom, 1 queen bed, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Marathon
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
4 bedrooms, 4 beds, 3.5 bathrooms
3–10 Oct
5.0 out of 5 average rating, 6 reviews
Guest favourite
Apartment in Key West
Penthouse Waterfront Dock Pool Condo Near Duval St
4 bedrooms, 11 beds, 4 bathrooms
13–18 Oct
4.9 out of 5 average rating, 265 reviews
Guest favourite
Home in Key West
Thompson Island USA !! Your Key West Retreat !!
9 bedrooms, 10 king beds, 6.5 bathrooms
15–20 Sept
4.79 out of 5 average rating, 105 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
19–24 Sept
4.91 out of 5 average rating, 562 reviews
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
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, 130 reviews
Featured hotel
Hotel in Key West
Classic Double Queen City/Balcony
1 bedroom, 2 queen beds, 1 bathroom
15–20 Sept
4.81 out of 5 average rating, 74 reviews