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
2 Baths
Sleeps 4
Type of property: Townhouse
Area: Old Town

ISLAND WIND: Welcome to a tropical sun-drenched oasis in the heart of Old Town. This charming 2 bedroom 2 bath Bahamian-style townhome, with tin roof and white spindled decks reminiscent of Old Key West, is located in award-winning Windward Park, a gated and secure compound. Soothe your weary muscles in your private jacuzzi after taking in the sights all day.


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

TRUMAN'S HIDEAWAY: It's hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House. Located in the exclusive Harbour Place complex, it has all the comforts of home and more.  Conveniently located in Truman Annex, within walking distance of all Key West activities, you'll be tempted to return again and again.


Call For Availability and Pricing
2 Bedrooms
2½ Baths
Sleeps 4
Type of property: 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
2½ Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

DUVAL ON THE SQUARE (monthly rental):  Located at the Duval Square townhomes directly on Duval but above all the hubbub. The townhomes are built on the second and third story of the complex with community pool overlooking Duval Street. This lovely 2 bedroom 2.5 bath townhome is available for a relaxing, luxurious month in Paradise.


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

CONCH WIND:   Conch Wind is the property you have been hunting for! This Conch-style townhome located in Old Town Key West is nestled in a quiet, secured compound, featuring 1 bedroom with bath ensuite on the first floor and the Master bedroom with bath ensuite upstairs. A porch and second floor balcony overlook the 50 foot pool, offering lots of room for rest and relaxation.


Call For Availability and Pricing
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.


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

CAPTAINS WHEEL: Take control of your vacation, be the master of your fate. Captains Wheel will not disappoint. Situated on the corner of Southard and Emma


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

SHIPYARD TREASURE: 2 bedroom 1 bath upstairs condo centrally located to all the sights and attractions of Old Town Key West including the beach at Fort Zachary Taylor State Park. Enjoy a cocktail on your balcony while watching the people stroll by and let the tropical breezes refresh your senses. ASK ABOUT OUR SPECIAL MONTHLY RATES DURING SUMMER MONTHS.


Call For Availability and Pricing
2 Bedrooms
1 Bath
Sleeps 4
Type of property: 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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4 Bedrooms
3½ Baths
Sleeps 8
Type of property: Home
Area: Old Town

THE DOLPHIN HOUSE: The Dolphin House Key West Vacation Rental is comprised of a bright and open main house and a lovely and bright guesthouse, with a pool and outdoor living space comfortably nestled in between. Plenty of room for friends or family gatherings.  Located in Truman Annex within walking distance of all Key West has to offer.  


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.


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1 Bedroom
1½ Baths
Sleeps 4
Type of property: Cottage
Area: Old Town

TRANQUILITY: This charming split level cottage offers 1 bedroom 1 full bath upstairs with sleeper sofa and half-bath downstairs. Cozy furnishings, soothing colors and modern conveniences make this the perfect spot for your visit to Key West. Stay in the heart of Old Town and walk to all there is to see on our island Paradise.


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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.


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.


Call For Availability and Pricing
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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