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Key West Time
September 16th
8:28pm · 83°F

Confessions of a KeyWest House Lover ...

Historic Key West Cottage Preserved Key West Cottage Preserved

(Or ... How it all Began)

My love affair with Key West houses started over two decades ago. I thought I was taking a short get-away to Key West, Florida, and well . . . the rest is history. The ‘quick trip’ lingered into an extended stay that never really ended as I was carried away by the exotic island life-style. Before I knew it I’d had fallen in love … with the story-book Key West houses and charming old world neighborhoods.

As I ponder back on how this happened, I recall how truly enamored I was by the entire laid-back island scene. As I strolled down the tree-lined streets past 1900’s Victorian houses tucked behind white picket fences, I had no idea that these memorizing moments would inspire my vacation rental business.

Few world destinations have such an awesome display of original century-old Victorian and Caribbean architecture, as Old Town Key West. Old island houses stand like art pieces in our modern times – porches preened and freshly painted gingerbread trim are lushly framed with tropical landscaping. Standing today as tributes to world explorers  of the 1800’s, when seafaring traders were ship builders-cum house builders, the huge collection of old wooden Key West houses were crafted without blueprints or modern tools.

Pulling from their memories of homes left behind, the original KeyWest builders were influenced by New England Victorian, Bahamian, African, and Creole designs. The display of architectural diversity we enjoy today was built in a fantastically spontaneous way!

I found an old Key West map showing how ‘Classic Revival’ estates with spacious porches sprang up next door to tiny 3- room ‘cigar makers’ cottages. Small Bahamian houses with wide porches and low roof lines were nestled up to grand romantic Queen Anne mansions. Then the entire collection of these diverse structures became neatly unified with shiny tin roofs and block-after-block of white picket fences, and a glorious showing of tropical flowers.

As I rapidly fell in love with the neighborhoods of Key West I started dreaming about owning my own Key West cottage. I imagined and pondered what it could be like to fulfill my infatuation.  I was no stranger to renovating and decorating houses, and in fairly short order, my fantasies became focused, and next thing I knew I owned my first ‘fixer upper’ in Old Town Key West!

Built in 1918, my old ‘shot gun’ Key West cottage was “born” the same year as my father and somehow that made it feel like destiny. Good thing ‘beauty is in the eyes of the beholder’, because even though the floor listed to the left and the paint was peeling, it had ‘good bones’ and I threw my heart-and-soul into making it shine! Thank goodness I was no stranger to hard work since back in those days I had no budget to speak of and had to do most of the labor myself.
With undying determination my tiny cottage was charmingly refreshed, romantically decorated, and ready to live in within several months.  I loved it dearly and named it “Eureka” after the town I grew up in since for me it represented new beginnings.

As fate would have it I never really settled into to my Eureka cottage. I needed to rent it occasionally to offset the costs of keeping it. So ... I started to offer it as a vacation rental cottage, to couples or singles, who wanted a vacation in a charming little romantic Key West cottage.

In those days I rented my cottage mostly by word-of-mouth and it was becoming a popular Key West rental at the same time that the internet was just catching on. It seemed to naturally grow into a unique business when internet marketing of vacation rentals was just beginning.  As time whizzed by and the internet rapidly became part of everyday life, I was diligent about building the business.

In a few years time I fell more deeply in love with Key West houses and acquired more properties to renovate and decorate. With the same commitment as my little Eureka cottage, I offered them for rent as unique vacation rentals. Within a few years time people were asking me to help decorate, market and rent their privately owned historic Key West houses.

Today Vacation Homes of Key West (VHKW) has grown to include an exclusive inventory of privately owned vacation rental properties.  Our beautiful website is informative and easy to navigate and features professional architectural photographs with detailed property descriptions that read more like a beautiful home magazine. We also feature a custom interactive Google map that helps you find the ideal vacation rental property in the Key West neighborhood that is just right for you.

As I look back nostalgically on the last two decades, it's fun to reminisce about how an innocent love affair (of a then young woman) with the time honored historic houses of Key West, turned into a wonderful business. We love giving  others the unique opportunity to really live their vacation in one of Key West’s most sustainable treasures ... a privately owned Key West home.



Latest Pins On Pinterest

A gorgeous shot from above of Key West, Florida, with the White Street Pier in clear view. #keywestflorida #island #islandlife #ocean #airplane
This charming vestibule is what you see when you walk through the front door at Key West Poolside Loft. Climb the stairs to the bright and open living and dining area!
This calming space is the perfect place to recharge at the end of the day.
There's space for three to sleep in this colorful and comfortable sleeping loft.
How amazing would it be to wake up to this view every morning? The private pation at Key West Poolside Loft overlooks the sparkling swimming pool and the peaceful Truman Annex community.
The view of the open living and dining area at Key West Poolside Loft, viewed from the sleeping loft.
This bright and open living space is located in Key West Poolside Loft, a 2-bedroom loft condo in Truman Annex.
The front door leading into Key West Poolside Loft, a two-bedroom condo in the Truman Annex community.
Key West is filled with whimsical, cheeky signs like this one. “Showers $1.00, To Watch $2.00.” 🤣 #keywestflorida #signs #funny #silly
The Florida Keys are home to some of the most stunning sunsets in the world. #sunset #sunsetphotography #ocean #oceanviews #sea #vacation #florida