Key West Vacation Rentals

Old Town ~ Key West Vacation Rentals

Old Town is the name given to the historic district of the island of Key West, Florida.  It is roughly the western half of the island. It is also where the central business district and majority of tourist attractions are located.   

One of the main reasons for the island's popularity as a vacation destination, aside from the year-round perfect climate, is the fascination with the Old World scale and extraordinary number of 19th century houses in Old Town; it is, in fact, the largest historical district of wooden structures on the Department of the Interior's National Register of Historic Places. That so many wooden houses from the last century still exist in such close proximity is due to a number of historical reasons. During the 1930s, when most parts of the U.S. were considering Victorian buildings outmoded and replacing them with structures in a modern idiom, Key West was too impoverished to partake in wanton demolition.

Key West architecture is a product of nearly two centuries of growth and change, influenced by a variety of factors:

The region's natural resources offered limited building materials. South Florida slash pine -- Dade County pine -- proved to be hard and resistant to decay, but lumbering eventually depleted supply. The cultural heritage of incoming settlers also influenced architecture. Wreckers from the Bahamas arriving before the Civil War constructed simple, well-proportioned buildings exemplifying the best of vernacular architecture. 

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

TROPICAL DREAMING: This tropical 2-bedroom home with sleeper sofa offers all the comforts of home. There are classic art features, hardwood floors, tall ceilings, and a true Key West feel. Sip a con leche on the back deck in the morning, swim and sun in the afternoon in your private pool, then head 1 block to Duval Street for the eclectic nightlife. It does not get better than this!


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.


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2 Bedrooms
2 Baths
Sleeps 5
Type of property: Condo
Area: Old Town

PARROT PERCH: Located in the gated community known as Truman Annex, you are in walking distance of all the activities to experience while visiting our island paradise. This 2nd floor condo with 2 bedrooms 2 baths and sleeper sofa offers a welcome respite in a great location and a great value for a great vacation.


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

A PLACE IN PARADISE:  You will experience true Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-style townhome in prestigious Truman Annex. Spend your vacation in a quiet gated community surrounded by historic buildings and tropical flora that exemplifies the best of Key West. Walk two blocks to all that Duval Street has to offer.


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

NAUTICAL DREAMS (monthly rental): Here's the perfect spot for whatever you desire, parties or peace & quiet. This 2 bedroom 2 bath home, in a small compound of 8 cottages, opens from each bedroom and the living room onto a grand private deck with ample space for entertaining or relaxing with a book. Walking through this well-established local neighborhood is an added bonus.


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

SPA ON DUVAL: A tropical 2-story, 2 bedroom 2.5bath townhome located in the rooftop community of Duval Square where you only have to walk downstairs to great restaurants, specialty shops and the action of Duval Street. Catch the rays on the pool deck or soothe tired muscles in the private jacuzzi on your own deck. Spa On Duval is truly a Key West experience to enjoy.


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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.


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

FIRST BREATH (monthly rental): After all the hectic travel to get here, enter this lovely 3-bedroom 2-bath Conch home with pool located right in the middle of the action in Old Town Key West and take your First Breath.  Fenced in and lushly landscaped for privacy.  Walk or bike anywhere you want to go or plant yourself on the back deck at the cool and refreshing pool.  


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

AMELIA HOME:  A private Key West vacation home that is only four blocks from one of our most popular beaches on the Atlantic Ocean and one block from all the Duval Street entertainment.  This 2 bedroom 2.5 bath single family home with private pool is located in one of the most interesting neighborhoods in the historic district of Old Town Key West.


Call For Availability and Pricing
2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

DUVAL SEA TURTLE: This 2 bedroom 2.5 bath townhome with sleeper sofa offers comfort and space for a family of six. Conveniently located in the rooftop townhome community of Duval Square, you are close enough to the eclectic activity of Duval Street, and far enough to enjoy peace and quiet in the privacy of your own home.


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3 Bedrooms
2½ Baths
Sleeps 7
Type of property: Private Home
Area: Old Town

DUVAL PENTHOUSE:   A large luxury apartment located in downtown Key West with rooftop views of Duval Street.  This property has it all, fabulous location, beautiful furnishings and plenty of space to accommodate your friends and family. 3 bedrooms 3 bath on the 2nd and 3rd levels, with pool on the ground level.  Very chic and urban modern in our laid back island paradise.


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1 Bedroom
1 Bath
Sleeps 2
Type of property: Cottage
Area: Old Town

IBIS (monthly rental): Ibis is a wonderful 1 bedroom 1 bath home that shares the pool and laundry facilities in The Colony Suites compound. Just a couple of blocks to Duval Street, walking distance to restaurants, shopping and attractions of Old Town Key West. Live like a local and find out why we call Key West our island paradise.


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: Private Home
Area: Old Town

PERFECT PINEAPPLE (monthly rental): Long considered a sign of hospitality, the pineapple is now widely recognized as a sign of Welcome and Friendship...and so we welcome you to the Perfect Pineapple. This quaint Conch cottage, 2 bedrooms 1 bath has all the amenities for your visit, including a side yard where you can sunbathe, swim and BBQ to your heart's content.


 

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