Key West Vacation Rentals

All Vacation Rentals in Key West, FL

Below you will find a list of all of our Key West, Florida vacation rentals, a variety of properties listed alphabetically, along with photo and brief description. You can view additional pictures and detailed information about the property by clicking on the property name. Have fun browsing!!!

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  • 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.
  • Rates will be higher for special events and holidays.
  • We can only reserve properties 364 days in advance
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86 Properties Returned
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86 Properties Returned
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Call For Availability and Pricing
2 Bedrooms
2 Baths
Sleeps 6
Type of property: Condo
Area: Ocean Side

4 PALMS: 2 bedroom 2 bath condominium with sleeper sofa offers your family the peace and tranquility you want while home, within minutes of the hectic lifestyle of downtown. Condo complex offer jacuzzi, pool, BBQ and tennis courts for your vacation pleasure. Located next to Smathers Beach where you can walk to promenade on the Atlantic Ocean witnessing magnificent sunrise.


Call For Availability and Pricing
3 Bedrooms
2½ Baths
Sleeps 6
Type of property: Private Home
Area: Old Town

FAN-tastic GETAWAY (monthly rental): This home has everything, including a bit of Key West history. Formerly owned by actress and fan dancer, Sally Rand, this spacious, fully renovated 3-bedroom, 2.5 bath home in the Old Town neighborhood known as The Meadows, with luxurious pool, chef's kitchen and outdoor great room.


Call For Availability and Pricing
2 Bedrooms
2½ Baths
Sleeps 4
Type of property: Private Home
Area: Old Town

ARTIST GARDEN:  A bright and breezy 2 bedroom 2.5 bath private home located in the prestigious Admirals Lane neighborhood of Truman Annex, a gated community within Old Town Key West. This property is in the ideal location, in walking distance to all Old Town has to offer, including the beautiful beach at Fort Zachary Taylor State Park.


Call For Availability and Pricing
2 Bedrooms
2 Baths
Sleeps 5
Type of property: Condo
Area: Old Town

SUNDOWN REFUGE: Balmy breezes, brilliant sunshine and magnificent sunsets await you at Sundown Refuge, located in the exclusive Harbour Place condominium complex in secluded Truman Annex. Lots of open spaces, perfect for entertaining or keeping it low-key and intimate. Easy walking distance to all Key West has to offer.


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3 Bedrooms
2 Baths
Sleeps 6
Type of property: Cottage
Area: Old Town

BOWE CONCH HOUSE: The Bowe Conch House has evolved within the Thomas family, Conchs, born and raised in Key West, for more than 4 generations.  Ethel Bowe-Thomas purchased the house in the 1930's, raised her family there, planted the massive poinciana tree that offers shade in the backyard, and now her family wants to share it with you.  A unique opportunity to experience life in Key West through the eyes of a Conch.


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2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

DUVAL BREEZE:  Enjoy the great location of  this beautiful 2 bedroom 2.5 bath townhome located in the gated rooftop community of Duval Square. This great location is steps away from fantastic restaurants, nightlife, bars and shopping on Duval Street in Old Town Key West.  Check out chaotic Duval Street, then relax  on your private balcony.  Ahhh...


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2 Bedrooms
1 Bath
Sleeps 4
Type of property: Condo
Area: Old Town

SIESTA BAY: Beautiful 2 bedroom 1 bath 2nd floor condo in Truman Annex, just steps away from the shared pool and a short walk to Fort Zachary Taylor State Park. Anything you want to do on our island paradise is within a few blocks. Enjoy quiet solitude in this home in between visits to chaotic Duval Street, then do it again and again.


Call For Availability and Pricing
3 Bedrooms
3½ Baths
Sleeps 7
Type of property: Private Home
Area: Old Town

BAHAMA HOUSE: Location, location, location! New and totally gorgeous, this spacious house is conveniently located on a quiet street in the heart of Old Town Key West only half a block from the fabulous shops, activities, restaurants and nightlife on Duval Street. Lounge at the pool in total privacy and solitude by day; take the walk around the corner to experience Key West nightlife.


Call For Availability and Pricing
2 Bedrooms
2 Baths
Sleeps 6
Type of property: Condo
Area: Ocean Side

PAPAYA PLACE: This spacious 2 bedroom 2 bath condominium at 1800 Atlantic offers a wonderful relaxing view of the nature preserve next door and the ocean beyond. Well-equipped with all the modern conveniences. Enjoy the peace and quiet of the tucked away balconies, far from the reaches of the world, allowing you to be lost in the tropical breezes.


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1 Bedroom
2 Baths
Sleeps 2
Type of property: Private Home
Area: Old Town

TROPICAL CASITA: It is rare you find a true jewel like Tropical Casita, nestled in a sweet little spot amid lush landscaping and secluded tranquility.  Languish in the grandiose bedroom on the second level, unwind around the pool, dine under the stars and sunbathe on the private upper level deck.  Decadence at its best.


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3 Bedrooms
3 Baths
Sleeps 8
Type of property: Townhouse
Area: Stock Island

Coral Casita - Weekly Vacation Rental Completely Re-Designed, Re-Decorated and Ready for your island adventures! When Key West is calling your name and nothing else will do. Spacious 3-bedroom townhome in the Coral Hammock gated community with pool - designer decorated.


Call For Availability and Pricing
3 Bedrooms
2 Baths
Sleeps 8
Type of property: Private Home
Area: Mid Town

FLAGLER STATION (monthly rental): This one just arrived and it is a true gem! Flagler Station was just remodeled, refurbished and re-furnished. High speed WIFI and state-of-the-art electronics, top-of the-line gourmet kitchen and luxury linens make this home the one you'll return to year after year.


Call For Availability and Pricing
2 Bedrooms
1 Bath
Sleeps 4
Type of property: Condo
Area: Old Town

KEY WEST CHARMING: This downstairs 2 bedroom 1 bath Shipyard condo is located in prestigious Truman Annex, a gated community within Old Town Key West. Take advantage of the ideal location and convenience of walking to anything you would want to do while visiting our lovely island. Prepare to be charmed.


Call For Availability and Pricing
2 Bedrooms
2½ Baths
Sleeps 4
Type of property: Private Home
Area: Old Town

VERANDAH (monthly rental): Tucked away on Frances Street lies your island escape called Verandah, named for the lanai surrounded by Bahama shutters allowing tropical breezes to waft through. A stunning 2 bedroom 2 bath home with private pool in a quiet residential neighborhood with plenty of space for your family to stay and play!


Call For Availability and Pricing
2 Bedrooms
1 Bath
Sleeps 4
Type of property: Condo
Area: Old Town

SUNSET CELEBRATION: 2 bedroom 1 bath Shipyard condo located in Truman Annex, in walking distance of anything you want to explore on our island paradise.  Newly renovated with a bright, tropical flair and fully stocked with all the conveniences of home.    Clean, serene and ready to make your visit to Key West one you'll cherish for years to come.


 

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