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Search results; Over 1,000 homes in Key West

Guest favourite
Apartment in Key West
The Samana Cay | Tropical, Airy Retreat w/ Pool
2 bedrooms, 3 beds, 2 private bathrooms
12–17 Sept
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4.91 out of 5 average rating, 22 reviews
Top guest favourite
Apartment in Key West
Boat Slip - Waterfront Condo - Key West Pool
2 bedrooms, 4 beds
15–20 Sept
5.0 out of 5 average rating, 7 reviews
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
Boat in Key West
Serenova - 58' Leopard Catamaran
3 bedrooms, 3 queen beds
9–14 Oct
New place to stay
Guest favourite
Home in Key West
Gone Coastal 2
3 bedrooms, 5 beds
25–30 Sept
4.93 out of 5 average rating, 128 reviews
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
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds
13–18 Sept
4.83 out of 5 average rating, 30 reviews
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
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, 21 reviews
Superhost
Home in Key West
Poolside Paradise
3 bedrooms, 6 beds
11–16 Oct
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
Superhost
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, 5 reviews
Guest favourite
Apartment in Key West
Parking & Shared Pool - Casa Key West
3 bedrooms, 5 beds
14–19 Sept
4.71 out of 5 average rating, 173 reviews
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
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
Luxe
Home in Key West
The Rigby House - Pool, One block from Duval St
6 bedrooms, 6 beds
15–20 Oct
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Apartment in Key West
Gorgeous Ocean View in Paradise, Close to Key West
3 bedrooms, 4 beds
13–18 Sept
4.99 out of 5 average rating, 140 reviews
Guest favourite
Flat in Key West
Casa Caribe 2bed2bath sleeps 6 beautiful decorated
2 bedrooms, 3 beds
8–13 Sept
4.96 out of 5 average rating, 28 reviews
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds
6–11 Sept
5.0 out of 5 average rating, 8 reviews