There are many reasons why people love to visit and live in Key West – the perfect weather, the warm water, the laid back, quirky culture and artsy lifestyle are impossible to beat. But the distinctive historic architecture of Southernmost houses and buildings would be enough to keep Key West on the map alone. 
A morning stroll around the island’s “Old Town” – the historic district – reveals some of the delights to be found on every street – shady lanes overhung with lush foliage, bright flowered vines paint white picket fences painted with flowering vines, fanciful scrollwork detailing distinctive, wood homes.
The use of “gingerbread” – a scrollwork of elaborate design on eaves and balustrades – is quite common in Key West. The style was popular in the late 1800s when so many of Key West’s most beautiful homes were built. Some home owners had the designs of the millwork match their occupations. Legend has it that families agreed not to copy one another.
At 1117 Duval, the second floor gallery is skirted by a balustrade of whiskey and wine bottle shapes, as well as heart and diamonds. Yes, you guessed it, the house was a speakeasy, and now houses The Speakeasy Inn.
There are countless other delightful examples of gingerbread – palm trees, pineapples, the very popular fleur de lis, and of course, the ship’s wheel.
The Island City House Hotel – built originally as a private home in the 1880s for a Charleston Family and converted to accommodations to take advantage of the railroad’s arrival in 1912 -- has some lovely scroll work.
This photo of the family’s Carriage House, now the hotel’s Eaton Street entrance, details some intricate mill work both as brackets and to frame the hotel’s signs.
On one home, there was clearly a sense of humor at work – the wrap around porch of the home at 1020 Southard Street is bedecked with gingerbread men!
Some Key West homes are distinctively not of the “Olde” Island style – or island style at all. 925 Southard Street, tucked away behind succulents and cacti, large terra cotta pots, and reached by Spanish tile steps, suggests more Southwest Adobe than Florida Keys.
And this former Art Deco styled gas station is now the Eaton Street Seafood market.
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