Barefoot Bungalow~2 Bedroom, 2 Bathroom Home w/ Office, Pool and Tiki Hut!Key WestSleeps 4 pers.2 bedrooms1,270 ft²YardTerraceInternetFREE cancellation9.7Fantastic12 reviewsfrom$354per nightMore detailsBook on Vrbo
Seaport Sanctuary ~ Come and Enjoy this Romantic & Lovely Couples Hideaway!Key WestSleeps 4 pers.1 bedroom420 ft²PoolTerraceInternetFREE cancellation10Fantastic3 reviewsfrom$279per nightMore detailsBook on Vrbo
Colony Calypso - A quaint 1 Bedroom Cottage just two blocks to DuvalKey WestSleeps 4 pers.1 bedroom517 ft²PoolYardTerraceInternetFREE cancellation9.3Fantastic63 reviewsfrom$578per nightMore detailsBook on Vrbo
Coconut Palm Studio ~ Adult Only Studio, Community Pool & Close to Town!Key WestSleeps 2 pers.1 bedroom248 ft²PoolYardTerraceParking5 more units availableFREE cancellation9.6Fantastic366 reviewsfrom$325per nightMore detailsBook on Vrbo
Exclusive Key West Beach Front - 2Br Luxury Condo w/Gym and Pool Access (Newly Refurnished!)Key WestSleeps 6 pers.2 bedrooms1,894 ft²PoolBalconyParkingInternet9.2Fantastic41 reviewsfrom$781per nightMore detailsBook on Vrbo
Poolside Cottage #411Key WestSleeps 6 pers.1 bedroom700 ft²PoolHot tubTerraceParkingFREE cancellation9.8Fantastic62 reviewsfrom$305per nightMore detailsBook on Vrbo
~ Solaris Cottage ~ Live like a local in this bright and cozy retreat.Key WestSleeps 2 pers.1 bedroom527 ft²YardTerraceInternet2 more units available9.6Fantastic158 reviewsfrom$505per nightMore detailsBook on Vrbo
Sea Breeze - One Block from Duval StreetKey WestSleeps 6 pers.2 bedrooms797 ft²BalconyParkingInternetFREE cancellation9.3Fantastic50 reviewsfrom$961per nightMore detailsBook on Vrbo
Conch Cottage - Feels Like Home - 1Bd/1Bath - Hot TubKey WestSleeps 2 pers.1 bedroomPoolHot tubTerraceInternet9.6Fantastic79 reviewsfrom$513per nightMore detailsBook on Vrbo
By the Beautiful Sea - Key West Beach Front Condo - w Pool AccessSmathers BeachSleeps 6 pers.3 bedrooms1,389 ft²PoolSaunaHot tubBalcony9.1Fantastic59 reviewsfrom$796per nightMore detailsBook on Vrbo
New Pricing: Drive To Your Getaway - Big Pool, Steps to Beach & Free ParkingKey WestSleeps 12 pers.5 bedrooms2,691 ft²PoolBalconyYardParkingFREE cancellation9.9Fantastic102 reviewsfrom$2,065per nightMore detailsBook on Vrbo
~ Poinciana Treetop ~ Casual second floor duplex 2 blocks from Duval Street!Key WestSleeps 3 pers.1 bedroom614 ft²BalconyParkingInternetOne more unit available9.8Fantastic72 reviewsfrom$456per nightMore detailsBook on Vrbo
Fully renovated Condo with Private Balcony, Shared Pool, Hot Tub and ParkingKey WestSleeps 6 pers.2 bedroomsPoolHot tubBalconyParkingFREE cancellation9.8Fantastic72 reviewsfrom$428per nightMore detailsBook on Vrbo
Poolside Queen Room Steps from Duval!Key WestSleeps 2 pers.1 bedroom194 ft²PoolHot tubTerraceParking2 more units availableFREE cancellation10Fantastic149 reviewsfrom$382per nightMore detailsBook on Vrbo
Seaport Suite - Steps from Duval StreetKey WestSleeps 12 pers.4 bedrooms1,593 ft²Hot tubBalconyYardInternetFREE cancellation8.5Very good12 reviewsfrom$1,239per nightMore detailsBook on Vrbo
Commodore's Cove - One block from Duval StKey WestSleeps 12 pers.4 bedrooms1,442 ft²BalconyParkingInternetFREE cancellation8.8Very good23 reviewsfrom$1,281per nightMore detailsBook on Vrbo
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balconyKey WestSleeps 6 pers.2 bedrooms797 ft²PoolHot tubBalconyParkingFREE cancellation9.1Fantastic40 reviewsfrom$547per nightMore detailsBook on Vrbo
Blue Bungalow ~ 2 Bedroom Townhome in Truman Annex Community with Pool!Key WestSleeps 6 pers.2 bedrooms958 ft²PoolBalconyParkingInternetFREE cancellation9.7Fantastic46 reviewsfrom$468per nightMore detailsBook on Vrbo
Feb 3-10 $245 off the rates close beach full kitchen & patioKey WestSleeps 2 pers.1 bedroom495 ft²TerraceParkingInternetFREE cancellation9.5Fantastic174 reviewsfrom$254per nightMore detailsBook on Vrbo
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk EverywhereKey WestSleeps 8 pers.3 bedrooms2,217 ft²PoolHot tubBalconyParkingOne more unit availableFREE cancellation9.7Fantastic198 reviewsfrom$1,042per nightMore detailsBook on Vrbo
Special @109.lodg. 9-14 to 10-7 With 4 night stay 4th night Free lodging!Key WestSleeps 2 pers.1 bedroom495 ft²TerraceParkingInternetFREE cancellation9.1Fantastic133 reviewsfrom$248per nightMore detailsBook on Vrbo
Key West Oasis - Truman Annex EstateKey WestSleeps 8 pers.5 bedrooms3,240 ft²PoolHot tubBalconyYardFREE cancellation10Fantastic3 reviewsfrom$1,800per nightMore detailsBook on Vrbo
Breezy Bungalow | Close 2 Zachary Taylor State Park & Beach | Month-Long StaysKey WestSleeps 4 pers.2 bedrooms958 ft²PoolBalconyParkingInternetFREE cancellation9.1Fantastic16 reviewsfrom$340per nightMore detailsBook on Vrbo
Upscale end unit home @ Truman Annex close to Duval StKey WestSleeps 3 pers.1 bedroomPoolBalconyParkingInternetFREE cancellation9.9Fantastic67 reviewsfrom$259per nightMore detailsBook on Vrbo
Little Paradise, Historic Harbor Old Town Key West 2/1.5Key WestSleeps 4 pers.2 bedrooms872 ft²TerraceInternetFREE cancellation8.2Very good25 reviewsfrom$608per nightMore detailsBook on Vrbo
Shipyard 197-Condo in Truman Annex-2 bedroom 1 bath, close to Duval w/ poolKey WestSleeps 4 pers.2 bedrooms592 ft²PoolTerraceParkingInternet9.4Fantastic40 reviewsfrom$197per nightMore detailsBook on Vrbo
The Quarterdeck ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Shipyard Unit!Key WestSleeps 4 pers.2 bedrooms678 ft²PoolBalconyYardParkingFREE cancellation9.0Fantastic49 reviewsfrom$201per nightMore detailsBook on Vrbo
New Monthly Rental, spacious, private yard, Old Town, pets welcomeKey WestSleeps 4 pers.2 bedrooms1,130 ft²BalconyInternetFREE cancellation10Fantastic10 reviewsfrom$217per nightMore detailsBook on Vrbo
Unique Home with loft @ Truman AnnexKey WestSleeps 4 pers.1 bedroomPoolBalconyParkingInternetFREE cancellation9.7Fantastic47 reviewsfrom$259per nightMore detailsBook on Vrbo
Secluded Casa Monthly Rental - Spacious Apartment, Overlooks Pool & Garden.Key WestSleeps 2 pers.1 bedroom646 ft²PoolYardTerraceParkingFREE cancellation10Fantastic21 reviewsfrom$196per nightMore detailsBook on Vrbo
