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

BEACH HOUSE CONDO:   A beautiful 2 bedroom 2 bath Shipyard condominium, located in the prestigious Truman Annex community. This gated community in Old Town Key West is ideal -- only 2 blocks from bars, restaurants and shopping on famous Duval Street and walking distance to all of the attractions you came here to see.


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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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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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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.


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

EMMA'S SECRET (monthly rental):  Luxurious 2 bedroom 1 bath condominium located in the historic Bahama Village neighborhood of Old Town offers all the amenities of home.  Enjoy the tropical backyard ambience with jacuzzi, pool and tiki hut.   Located in walking distance to Duval Street, the heart of Key West with all the activities, restaurants, speciality shops and nightlife.


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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.


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4 Bedrooms
3 Baths
Sleeps 8
Type of property: Luxury
Area: Old Town

CASA ON CASA--  So simple yet elegant, intimate yet spacious, "Casa on Casa"; offers a unique Key West experience that will linger in your memory for years to come. Located in the exclusive Casa Marina neighborhood, it is separated from the beach by a park with a fitness circuit, dog park, playground, tennis courts and pickleball courts. The historic Casa Marina hotel is at the other end of the block, and all of Old Town is a quick bike ride away.


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

KEY WEST GINGER HOUSE: An absolute jewel a few doors from Duval Street, this single family home is named for the breathtaking ginger plants blooming in our tropical paradise. Featuring 2 bedrooms and 2 full baths with a private jacuzzi in the garden. Soothe your muscles after a full day of partying downtown.


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

SUNNY DAYS - Monthly rental Key West, beautifully maintained while retaining its original style and structure. Dade County pine is throughout the property, lots of French doors and windows to bring in the sunshine, and lots of privacy within the cottage grounds and within the compound community. 


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2 Bedrooms
2½ Baths
Sleeps 4
Type of property: Cottage
Area: Old Town

GREEN ORCHID (monthly rental): Dreaming of living like a local in Key West? Dream no more. Green Orchid offers a true Conch Cottage experience situated on a narrow lane in one of the last historic Old Town neighborhoods. Inside you'll live with all the modern conveniences and furnishings; outside you'll feel you've been transported to years gone by.


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3 Bedrooms
2½ Baths
Sleeps 6
Type of property: Luxury
Area: Old Town

ECCO DOMANI (monthly rental):  Meaning "Here Tomorrow" this is a beautiful 3 story home with private pool, off street parking and attractive appointments -- a wonderful Key West escape.  Tucked away in a quiet spot in Old Town yet only one block from the action on Duval Street.  Dream the day away in your own private sanctuary; spend the evening taking in all Old Town Key West has to offer.


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2 Bedrooms
2 Baths
Sleeps 4
Type of property: Cottage
Area: Old Town

KEY LIME PIE (monthly rental): A little slice of paradise located one block from the Historic Seaport on a tiny lane. Close enough to bike to all the sights and attractions of Old Town; far enough away to forget you are staying right in the middle of the action. 2 bedrooms 2 baths with private swim spa, this home will give you a reason to say, Ahhh...


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4 Bedrooms
4 Baths
Sleeps 8
Type of property: Private Home
Area: Old Town

BLOOM'N PARADISE: Relax in luxury in this beautiful Truman Annex private home with pool and sun deck. 3 bedrooms and 3 bathrooms in the main house plus a pool house with 1 bedroom 1 bath offers room for friends and family to enjoy peace and solitude while at home, with the chaotic nightlife of downtown Key West just 2 blocks away.


 

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