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: 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 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.


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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.


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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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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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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.


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5 Bedrooms
5½ Baths
Sleeps 12
Type of property: Private Home
Area: Old Town

CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street, you'll spend most of your time in the magnificent pool in your private backyard. Duval Street, pool and sunshine - a perfect recipe for Key West living.


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6 Bedrooms
5½ Baths
Sleeps 14
Type of property: Private Home
Area: Old Town

DUVAL COMPOUND: Perfect location! In the heart of historic Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling 6 bedroom, 5 full bathroom, 2 half bath compound has two private swimming pools, endless porches, terraces and a huge, fabulous roof deck that overlooks the action on Duval Street.


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

OSPREY: This quaint cottage is located in The Colony Suites, a charming and secluded Key West style compound nestled in the heart of historic Old Town Key West, just 2 blocks from Duval Street. Compact and well-appointed, it is perfect for two people who want to relax, swim and walk around Duval Street, day after day.


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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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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.  


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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.


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2 Bedrooms
1 Bath
Sleeps 3
Type of property: Cottage
Area: Old Town

William's Loft (Monthly Rental)
Located in Old Town in a small, quiet compound of cottages sits William's Loft in one of Key West's most desirable neighborhoods. A secluded compound surrounded by lush tropical foliage make this the idyllic escape. The cottage is exactly as you envision in Key West with distressed wood floors and Dade County Pine plus all the modern amenities of home.


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

BAHAMIAN REED: 2 bedroom 1.5 bathroom townhome located in Truman Annex in Old Town Key West. Conveniently located near all the reasons you came to Key West:  sunset celebration, beach, bars, restaurants, galleries, theater.  This will be the place you'll return to again and again.


 

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