Best price vacation rentals • 143 Listings
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Paradise Place by AvantStay | Condo w/ Shared Pool
Paradise Place by AvantStay | Condo w/ Shared Pool
Up to 4 Guests
$185
$394
Not listed
Beautiful private home in Old Town with a Pool
Beautiful private home in Old Town with a Pool
Up to 5 Guests
$270
$287
Not listed
Land Of Love by AvantStay|Pet-Safe, Shared Pool
Land Of Love by AvantStay|Pet-Safe, Shared Pool
Up to 4 Guests
$110
$172
Not listed
Southard Comfort ~ Feel The Key West Vibe
Southard Comfort ~ Feel The Key West Vibe
Up to 6 Guests
$1,237
Not listed
Bayview North One: Waterfront 4 Bedroom 4 Bath Con
Bayview North One: Waterfront 4 Bedroom 4 Bath Con
Up to 8 Guests
$719
Not listed
Casablanca Too ~ Chicly Updated Home With Hot Tub
Casablanca Too ~ Chicly Updated Home With Hot Tub
Up to 2 Guests
$576
Not listed
Upper Bayview South: Waterfront 4 Bedroom Condo at
Upper Bayview South: Waterfront 4 Bedroom Condo at
Up to 8 Guests
$719
Not listed
Upper Sunset North: Luxury 4 Bedroom Condo at Bayf
Upper Sunset North: Luxury 4 Bedroom Condo at Bayf
Up to 8 Guests
$608
Not listed
Seafarer's Refuge: 3 Story spacious conch style ho
Seafarer's Refuge: 3 Story spacious conch style ho
Up to 10 Guests
$899
Not listed
2/2 Fully Updated Old Town Waterfront Corner Condo
2/2 Fully Updated Old Town Waterfront Corner Condo
Up to 6 Guests
$550
Not listed
Waterfront Penthouse sleeps 16 w/Pool & Boat Dock
Waterfront Penthouse sleeps 16 w/Pool & Boat Dock
Up to 16 Guests
$1,350
Not listed
Downtown Waterfront 2/2 Dock & Pool Pet-Friendly
Downtown Waterfront 2/2 Dock & Pool Pet-Friendly
Up to 6 Guests
$550
Not listed
Large 2/2 Waterfront Condo Great View Pool & Dock
Large 2/2 Waterfront Condo Great View Pool & Dock
Up to 6 Guests
$550
Not listed
Downtown 4/4 Waterfront Penthouse Pool, Dock, Pet
Downtown 4/4 Waterfront Penthouse Pool, Dock, Pet
Up to 14 Guests
$1,350
Not listed
Downtown Waterfront Penthouse Pool, Dock, Parking
Downtown Waterfront Penthouse Pool, Dock, Parking
Up to 16 Guests
$1,350
Not listed
Dominica Pelican Landing condo w/ 3beds, boat slip
Dominica Pelican Landing condo w/ 3beds, boat slip
Up to 8 Guests
$400
Not listed
Bayview Middle: Waterfront 3 Bedroom Condo at Bayf
Bayview Middle: Waterfront 3 Bedroom Condo at Bayf
Up to 6 Guests
$608
Not listed
Captain's Daughter: Oversized home for the whole f
Captain's Daughter: Oversized home for the whole f
Up to 12 Guests
$1,034
Not listed
Villa Azul ~ Enjoy This Historic Home With Pool
Villa Azul ~ Enjoy This Historic Home With Pool
Up to 6 Guests
$461
Not listed
Key Limetini - Lovely Studio In Old Town Key West!
Key Limetini - Lovely Studio In Old Town Key West!
Up to 2 Guests
$170
Not listed
Modern in the Meadows - Chic Private Home & Pool
Modern in the Meadows - Chic Private Home & Pool
Up to 10 Guests
$230
Not listed
Casa de Rosalie by AvantStay | Month-Long Stays
Casa de Rosalie by AvantStay | Month-Long Stays
Up to 8 Guests
$170
Not listed
Paradise on White Street
Paradise on White Street
Up to 10 Guests
$635
Not listed
The Conch Chateau - Conch Home, Pool, Dog Friendly
The Conch Chateau - Conch Home, Pool, Dog Friendly
Up to 9 Guests
$170
Not listed
Old Town Key West Live like a local
Old Town Key West Live like a local
Up to 4 Guests
$225
Not listed