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Search results; Over 1,000 homes in Key West

Superhost
Cottage in Key West
Darling of Duval at Old Town
2 bedrooms, 2 beds, 2 private bathrooms
16–21 Sept
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4.77 out of 5 average rating, 39 reviews
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds
12–17 Sept
4.71 out of 5 average rating, 35 reviews
Featured hotel
Room in Key West
Superior King Pool/Balcony
1 king bed
28 Sept – 3 Oct
4.74 out of 5 average rating, 19 reviews
Top guest favourite
Home in Key West
Casa Cristol - Truman Annex
3 bedrooms, 3 beds
13–18 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Boat in Key West
All Inclusive! Snorkel • Sail • Sun & Fun
3 bedrooms, 3 queen beds
17–22 Sept
4.88 out of 5 average rating, 177 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
17–22 Sept
4.91 out of 5 average rating, 561 reviews
Superhost
Villa in Marathon
New Aqua Lodge 2Beds 1 Bath with Full Kitchens
1 bedroom, 2 beds
13–18 Sept
4.86 out of 5 average rating, 616 reviews
Guest favourite
Boat in Key West
Waterfront & Heated Pool - Away Awai Floating Vill
2 bedrooms, 2 queen beds
12–17 Sept
4.93 out of 5 average rating, 87 reviews
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
Guest favourite
Home in Key West
Thompson Island USA !! Your Key West Retreat !!
9 bedrooms, 10 king beds
12–17 Sept
4.79 out of 5 average rating, 105 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, 17 reviews
Guest favourite
Tiny home in Key West
Downtown Studio half block from Duval w parking
1 bed
26 Sept – 1 Oct
4.86 out of 5 average rating, 478 reviews
Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds
13–18 Sept
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Apartment in Key West
Waterfront Condo | Pool, Dock, Parking, Sleeps 8
2 bedrooms, 4 beds
8–13 Oct
4.87 out of 5 average rating, 306 reviews
Guest favourite
Home in Key West
Gone Coastal 2
3 bedrooms, 5 beds
25–30 Sept
4.93 out of 5 average rating, 129 reviews
Top guest favourite
Flat in Key West
Duval Balcony - Suite Mischief
1 bedroom, 1 king bed
28 Sept – 3 Oct
4.88 out of 5 average rating, 813 reviews
Top guest favourite
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
Top guest favourite
Home in Key West
Pilar House
3 bedrooms, 3 beds
13–18 Dec
4.96 out of 5 average rating, 47 reviews