Property List

Below you will find a list of all of our Key West rental properties listed alphabetically. Along with the area of town they are located in and the type and size of the property.

You can view pictures and information about the property by clicking on the property name. Have fun browsing!!! Check here if you have certain amenities you desire in a rental property in Key West.

  • Winter rates apply from approximately December 15 – April 30.
  • Shoulder rates apply from approximately May 1 – May 30 and November 1 – December 14.
  • Summer rates apply from approximately June 1 – October 31.

A Zen GardenOCEAN VIEWTwo Bedroom Condo
A Place in ParadiseTRUMAN ANNEXTwo Bed Townhome
A Spa On DuvalOLD TOWNTwo Bed Townhome
A Suite ParadiseMID TOWN2 Bed Home - Monthly
Admiral's ParadiseTRUMAN ANNEXThree Bedroom Home
Amelia HomeOLD TOWNTwo Bedroom Home
Anne's HideawayOLD TOWN2 Bed Home - Monthly
AquamarineTRUMAN ANNEXTwo Bedroom Condo
Artist HouseOLD TOWNTwo Bed Townhome
Artist's CottageOLD TOWN1 Bed Home - Monthly
Atlantic BluesOLD TOWN1 Bed Home - Monthly
Babalu CottageOLD TOWNThree Bedroom Home
Bahama DreamingOLD TOWNThree Bedroom Home
Bahama HouseOLD TOWNThree Bedroom Home
Bahamian ReedTRUMAN ANNEXTwo Bed Townhome
Bamboo KeyTRUMAN ANNEXTwo Bedroom Condo
Banana KeyTRUMAN ANNEXTwo Bedroom Condo
Beach House CondoTRUMAN ANNEXTwo Bedroom Condo
Bird of ParadiseMID TOWN5 Bed Home - Monthly
Birds NestGOLF COURSE2 Bed Home - Monthly
Bloom'n ParadiseTRUMAN ANNEXFour Bedroom Home
Brisa del MarOCEAN VIEWTwo Bedroom Condo
CalypsoTRUMAN ANNEXTwo Bedroom Condo
Caribbean DuvalOLD TOWNTwo Bed Townhome
Casa ColonialOLD TOWN3 Bed Home - Monthly
Casa de VinoCORAL HAMMOCKThree Bed Townhome
Casa FloraGOLF COURSE2 Bed Home - Monthly
Casa La BrisaOLD TOWN3 Bed Home - Monthly
Casa LagunaGOLF COURSE4 Bed Home - Monthly
Casa LouisaOLD TOWNThree Bedroom Home
Casita de CatherineOLD TOWN1 Bed Home - Monthly
Coconut CottageOLD TOWN1 Bed Home - Monthly
Cold's Milk FarmOLD TOWN4 Bed Home - Monthly
Cold's Milk Farm ThreeOLD TOWN3 Bed Home - Monthly
Cole's CottageOLD TOWN2 Bed Home - Monthly
Conch CondoTRUMAN ANNEXTwo Bedroom Condo
Conch EscapeOLD TOWN2 Bed Home - Monthly
Conch WindOLD TOWNTwo Bed Townhome
Coral CaribeCORAL HAMMOCKTwo Bed Townhome
Coral CottageOLD TOWN1 Bed Home - Monthly
Corner PlaceGOLF COURSE2 Bed Home - Monthly
Crowner's JewelTRUMAN ANNEXTwo Bed Townhome
Duval BreezeOLD TOWNTwo Bed Townhome
Duval CompoundOLD TOWNSix Bedroom Home
Duval CourtyardOLD TOWNThree Bed Townhome
Duval PenthouseOLD TOWNThree Bedroom Home
Duval Sea TurtleOLD TOWNTwo Bed Townhome
Duval Street HideawayOLD TOWNTwo Bed Townhome
Egret CottageOLD TOWNOne Bedroom Home
Emma's EscapeOLD TOWN2 Bed Condo - Monthly
Emma's SecretOLD TOWN2 Bed Condo - Monthly
Finn KeyTRUMAN ANNEXTwo Bedroom Condo
Fleming Street GardensOLD TOWN2 Bed Home - Monthly
Florida PalmOCEAN VIEWTwo Bedroom Condo
HeronOLD TOWNOne Bedroom Home
IbisOLD TOWN1 Bed Home - Monthly
Isla ParaisoMID TOWN3 Bed Home - Monthly
Island PearlOLD TOWNOne Bedroom Home
Island SpiceTRUMAN ANNEXTwo Bed Townhome
Island TimeOLD TOWN3 Bed Home - Monthly
Island WindOLD TOWNTwo Bed Townhome
JosephineMID TOWN2 Bed Home - Monthly
Key Lime PieOLD TOWN2 Bed Home - Monthly
Key West CasaTRUMAN ANNEXThree Bedroom Condo
Key West CharmingTRUMAN ANNEXTwo Bedroom Condo
Key West Crown JewelOCEAN VIEWTwo Bedroom Condo
Key West FoundTRUMAN ANNEXTwo Bed Townhome
Key West Ginger HouseOLD TOWNTwo Bedroom Home
LakeviewGOLF COURSE2 Bed Home - Monthly
Land's EndOLD TOWN1 Bed Home - Monthly
Larkin HouseTRUMAN ANNEXTwo Bedroom Home
Lavender JungleTRUMAN ANNEXTwo Bedroom Condo
Leeward Isle Key West RetreatOLD TOWNTwo Bed Townhome
Linger LongerTRUMAN ANNEXTwo Bed Townhome
Mar Y SolOCEAN VIEWThree Bedroom Condo
Nantucket SouthTRUMAN ANNEXTwo Bedroom Condo
Nautical DreamsOLD TOWN2 Bed Home - Monthly
OspreyOLD TOWNStudio Condo
Papaya PlaceOCEAN VIEWTwo Bedroom Condo
Paradise PlaceOLD TOWNOne Bedroom Home
Parrot PerchTRUMAN ANNEXTwo Bedroom Condo
Perfect PineappleOLD TOWN2 Bed Home - Monthly
Potters CottageOLD TOWNThree Bedroom Home
Sand DollarTRUMAN ANNEXOne Bedroom Condo
Shipyard TreasureTRUMAN ANNEXTwo Bedroom Condo
Siesta BayTRUMAN ANNEXTwo Bedroom Condo
Southard RetreatOLD TOWN2 Bed Condo - Monthly
Southern ComfortGOLF COURSE2 Bed Home - Monthly
Southern WindOLD TOWNTwo Bed Townhome
Sundown CottageGOLF COURSE3 Bed Townhouse - Monthly
Sunny DaysOLD TOWN2 Bed Home - Monthly
Sunny ViewOLD TOWN1 Bed Home - Monthly
Surf SideOCEAN VIEWThree Bedroom Condo
Tee TimeGOLF COURSE3 Bed Home - Monthly
The HemingwayTRUMAN ANNEXTwo Bed Townhome
The Victoria HouseOLD TOWNFive Bedroom Home
Tobago HouseOLD TOWN1 Bed Home - Monthly
Tropical DreamingOLD TOWNTwo Bedroom Home
Tropical OasisMID TOWN2 Bed Home - Monthly
Tropical VineyardTRUMAN ANNEXOne Bedroom Condo
Varela CottageOLD TOWN1 Bed Home - Monthly
VerandahOLD TOWN2 Bed Home - Monthly
Villa SoleilTRUMAN ANNEXTwo Bed Townhome