Skip to Main Content.
Download the app button
Download the app button with download icon
Get the app
United States
Trip Boards
List your property
Help
My trips
Sign in
Vrbo just got better
Earn rewards across our family of brands with One Keyâ„¢
Sign in
Sign in as an owner
Learn about One Key
Feedback
Going to
Going to
Dates
Travelers
Adults
Adults
Decrease the number of adults
Increase the number of adults
Children
Ages 0 to 17
Decrease the number of children
Increase the number of children
I am traveling with pets
If checked, only properties that allow pets will be shown
Done
Search
Filters
Popular
Price
Rooms & spaces
Sort by recommended
240 properties
How our sort order works
Opens in a new window
Search results showing properties in Key West, Florida, United States of America. September 24, 2023 through September 28, 2023
Google map showing 258 properties
Key West is popular!
Only 13% of properties are available on our site for your dates.
Photo gallery for Ultimate Beach Adventure! Pool, Restaurant, Bar, Bike Rental, Gym,
For those who enjoy the pool over the beach, come relax poolside.
Show previous image for Ultimate Beach Adventure! Pool, Restaurant, Bar, Bike Rental, Gym,
Show next image for Ultimate Beach Adventure! Pool, Restaurant, Bar, Bike Rental, Gym,
Guesthouse · 4 min drive to the beach
Ultimate Beach Adventure! Pool, Restaurant, Bar, Bike Rental, Gym,
Sleeps 2 · 1 bedroom · 1 bathroom
May 20 - May 24
8.0/10
Very Good
(21 reviews)
8.0 out of 10 Very Good (21 reviews)
View details for price
More information about Ultimate Beach Adventure! Pool, Restaurant, Bar, Bike Rental, Gym,, opens in a new tab
Photo gallery for SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w/ Shared Pool!
Your retreat awaits
Show previous image for SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w/ Shared Pool!
Show next image for SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w/ Shared Pool!
Premier Host
Condo · 10 min walk to Florida Keys Beaches
SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w/ Shared Pool!
Sleeps 2 · 1 bedroom · 1 bathroom
May 20 - May 24
9.8/10
Exceptional
(51 reviews)
9.8 out of 10 Exceptional (51 reviews)
View details for price
More information about SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w/ Shared Pool!, opens in a new tab
Photo gallery for Traveler's Palm by Brightwild |Recently Updated!
Private Patio
Show previous image for Traveler's Palm by Brightwild |Recently Updated!
Show next image for Traveler's Palm by Brightwild |Recently Updated!
Premier Host
Apartment · 8 min walk to Florida Keys Beaches
Traveler's Palm by Brightwild |Recently Updated!
Sleeps 6 · 1 bedroom · 1 bathroom
May 20 - May 24
8.6/10
Excellent
(9 reviews)
8.6 out of 10 Excellent (9 reviews)
View details for price
More information about Traveler's Palm by Brightwild |Recently Updated!, opens in a new tab
Guesthouse · 3 min walk to South Beach
Experience All Of What Key West Has To Offer! Beach Access, 3 Pools, Spa!
Sleeps 2 · 1 bedroom · 1 bathroom
May 20 - May 24
7.8/10
Good
(6 reviews)
7.8 out of 10 Good (6 reviews)
View details for price
More information about Experience All Of What Key West Has To Offer! Beach Access, 3 Pools, Spa!, opens in a new tab
Guesthouse · 4 min drive to the beach
Excellent Choice! Family-friendly Room, Fantastic View, Outdoor Pool
Sleeps 2 · 1 bedroom · 1 bathroom
May 20 - May 24
5.6/10
(4 reviews)
5.6 out of 10 (4 reviews)
View details for price
More information about Excellent Choice! Family-friendly Room, Fantastic View, Outdoor Pool, opens in a new tab
Guesthouse · 3 min walk to South Beach
Perfect Location to Key West Action! Onsite Spa, Access to 2 Beaches, 3 Pools!
Sleeps 4 · 1 bedroom · 1 bathroom
May 20 - May 24
8.0/10
Very Good
(7 reviews)
8.0 out of 10 Very Good (7 reviews)
View details for price
More information about Perfect Location to Key West Action! Onsite Spa, Access to 2 Beaches, 3 Pools!, opens in a new tab
Guesthouse · 3 min walk to South Beach
Experience Florida Like Never Before! Oceanfront Pool, Nightlife, Beach Bar!
Sleeps 2 · 1 bedroom · 1 bathroom
May 20 - May 24
8.0/10
Very Good
(1 review)
8.0 out of 10 Very Good (1 review)
View details for price
More information about Experience Florida Like Never Before! Oceanfront Pool, Nightlife, Beach Bar!, opens in a new tab
House · 8 min walk to South Beach
Tortugas Harbor Suite | 1 Bed, 1 Bath
Sleeps 4 · 1 bedroom · 1 bathroom
May 20 - May 24
View details for price
More information about Tortugas Harbor Suite | 1 Bed, 1 Bath, opens in a new tab
Guesthouse · 4 min drive to the beach
Perfect Location for Your Next Getaway! Amazing Room w/ King Bed, Outdoor Pool
Sleeps 2 · 1 bedroom · 1 bathroom
May 20 - May 24
8.4/10
Very Good
(5 reviews)
8.4 out of 10 Very Good (5 reviews)
View details for price
More information about Perfect Location for Your Next Getaway! Amazing Room w/ King Bed, Outdoor Pool, opens in a new tab
Guesthouse · 4 min drive to the beach
Standard Two Queen Beds at The Gates Hotel Key West, Onsite Pool, Bike Rental!
Sleeps 4 · 1 bedroom · 1 bathroom
May 20 - May 24
10/10
Exceptional
(1 review)
10 out of 10 Exceptional (1 review)
View details for price
More information about Standard Two Queen Beds at The Gates Hotel Key West, Onsite Pool, Bike Rental!, opens in a new tab
House · 3 min walk to South Beach
Superior King ADA Accommodation at Southernmost Beach Resort
Sleeps 2 · 1 bedroom · 1 bathroom
May 20 - May 24
10/10
Exceptional
(1 review)
10 out of 10 Exceptional (1 review)
View details for price
More information about Superior King ADA Accommodation at Southernmost Beach Resort, opens in a new tab
Apartment · 6 min walk to Florida Keys Beaches
Yellow Room at Grand Maloney by Brightwild
Sleeps 2 · 1 bedroom · 1 bathroom
May 20 - May 24
10/10
Exceptional
(2 reviews)
10 out of 10 Exceptional (2 reviews)
View details for price
More information about Yellow Room at Grand Maloney by Brightwild, opens in a new tab
Apartment · 4 min walk to Florida Keys Beaches
Mesa House, Uno by Brightwild | Perfect Location
Sleeps 4 · 1 bedroom · 1 bathroom
May 20 - May 24
9.6/10
Exceptional
(24 reviews)
9.6 out of 10 Exceptional (24 reviews)
View details for price
More information about Mesa House, Uno by Brightwild | Perfect Location, opens in a new tab
Guesthouse · 1 min walk to South Beach
Duval Gardens King Adults Only at The Guesthouses at Southernmost Beach Resort
Sleeps 2 · 1 bedroom · 1 bathroom
May 20 - May 24
View details for price
More information about Duval Gardens King Adults Only at The Guesthouses at Southernmost Beach Resort, opens in a new tab
Guesthouse · 3 min walk to South Beach
Ultimate Key West Experience! Access to 2 Beaches, 3 Pools, Near Duval Street
Sleeps 2 · 1 bedroom · 1 bathroom
May 20 - May 24
10/10
Exceptional
(1 review)
10 out of 10 Exceptional (1 review)
View details for price
More information about Ultimate Key West Experience! Access to 2 Beaches, 3 Pools, Near Duval Street, opens in a new tab
Guesthouse · 3 min walk to South Beach
Paradise Getaway! Bike Rental, 3 POOLS, Bar, Short Walk to Southernmost Point!
Sleeps 4 · 1 bedroom · 1 bathroom
May 20 - May 24
View details for price
More information about Paradise Getaway! Bike Rental, 3 POOLS, Bar, Short Walk to Southernmost Point!, opens in a new tab
House · 8 min walk to South Beach
American Shoal Suite | 2 Bed, 1 Bath
Sleeps 6 · 2 bedrooms · 1 bathroom
May 20 - May 24
10/10
Exceptional
(2 reviews)
10 out of 10 Exceptional (2 reviews)
View details for price
More information about American Shoal Suite | 2 Bed, 1 Bath, opens in a new tab
Tell us how we can improve our site
Share feedback