Vacation Rentals in Key West, Florida
Discover 1,835 vacation rental properties in Key West. From 1 to 13 bedrooms. Average $560/night. 100% have pools.
1,835 verified listings
Book securely on VRBO
Prices updated March 2026
1,835 properties available
Showing 48 of 1,835 properties
Top Floor Ocean Views from every window Newly Renovated
2 beds 2 baths
PoolA/CWiFiBalcony
$437/night
Welcome to the Shady Palms - Private Pool - RealKeyWest
2 beds 2 baths
PoolA/CWiFiBalcony
$217/night
Caroline On My Mind-New Listing-Light, Bright and Airy!
2 beds 2 baths
PoolA/CWiFiBalcony
$222/night
Conch Cottage Retreat in the heart of Old Town Key West
2 beds 2 baths
PoolA/CWiFiBalcony
$291/night
PEARL COTTAGE ~ 3 Bedroom, 3.5 Bathroom Home with Pool!
3 beds 3 baths
PoolA/CWiFiBalcony
$475/night
SUNCATCHER~4 Bedroom, 4 Bathroom in Old Town with Pool!
4 beds 4 baths
PoolA/CWiFiBalcony
$699/night
King with Pool View & Terrace at The Gates Hotel Key West
1 bed 1 bath
PoolA/CWiFiBalcony
$249/night
SWEET LIKE SUMMERTIME ~ 3 BR/2Ba Home w/ Pool and Yard!
3 beds 2 baths
PoolA/CWiFiBalcony
$220/night
Charm is on order at Rose Key Cottage! Come check it out!
1 bed 1 bath
PoolA/CWiFiBalcony
$315/night
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
1 bed 1 bath
PoolA/CWiFiBalcony
$202/night
Old Town Key West Home w/ Pool! Walkable to Everything!
2 beds 2 baths
PoolA/CWiFiBalcony
$229/night
Amelia Home by AvantStay | In Historic Old Town w/ Pool
2 beds 2 baths
PoolA/CWiFiBalcony
$535/night
Luxury Galleon Resort & Marina 2 Bed/2 Bath Marina View
2 beds 2 baths
PoolA/CWiFiBalcony
$351/night
Pete's Cottages: Twin Cypress cottages steps from Duval
4 beds 2 baths
PoolA/CWiFiBalcony
$657/night
More destinations in Florida
Panama City Beach (4614)
Kissimmee (3730)
Davenport (2507)
Miami Beach (1899)
Cape Coral (1809)
Sarasota (1719)
Marco Island (1375)
Naples (1355)
Siesta Key (936)
Holmes Beach (770)
Clearwater (768)
Bradenton (551)
Orlando (458)
Miami (425)
Anna Maria (386)
Rotonda West (381)
Clearwater Beach (361)
Santa Rosa Beach (358)
Destin (250)
Gulf Shores (250)