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Search results; Over 1,000 homes in Key West

Top guest favourite
Home in Key West
Funky Chicken Cottage with Shared Pool in Paradise
3 bedrooms, 3 beds, 3 private bathrooms
10–15 Sept
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5.0 out of 5 average rating, 43 reviews
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds, 1 bathroom
13–18 Sept
4.84 out of 5 average rating, 32 reviews
Featured hotel
Room in Key West
Hearing Accessible Classic King City/Balcony
1 king bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Key West
Poolside Paradise
3 bedrooms, 6 beds, 3 bathrooms
11–16 Oct
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, 40 reviews
Top guest favourite
Apartment in Key West
Boat Slip - Waterfront Condo - Key West Pool
2 bedrooms, 4 beds, 2 bathrooms
24–29 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
17–22 Sept
4.91 out of 5 average rating, 561 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
Top guest favourite
Apartment in Key West
Coastline Comfort
2 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 11 reviews
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
Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 22 reviews
Guest favourite
Boat in Key West
Waterfront & Heated Pool - Away Awai Floating Vill
2 bedrooms, 2 queen beds, 2 bathrooms
10–15 Sept
4.93 out of 5 average rating, 87 reviews
Top guest favourite
Casa particular in Key West
Amazing Canal front home in KW!
4 bedrooms, 5 beds, 3 bathrooms
12–17 Sept
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Boat in Key West
All Inclusive! Snorkel • Sail • Sun & Fun
3 bedrooms, 3 queen beds, 2.5 bathrooms
10–15 Sept
4.88 out of 5 average rating, 177 reviews
Luxe
Home in Key West
Spindrift House at Lunara Bay
4 bedrooms, 7 beds, 4 bathrooms
13–18 Sept
4.85 out of 5 average rating, 99 reviews
Top guest favourite
Home in Key West
Pilar House
3 bedrooms, 3 beds, 2 bathrooms
13–18 Dec
4.96 out of 5 average rating, 47 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, 5 reviews
Top guest favourite
Flat in Key West
Newly Renovated 2/2 Bath Condo, with shared pool
2 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
4.99 out of 5 average rating, 87 reviews
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 9 reviews