Hemingway House, Key West – A Singular Structure in the Southernmost City
🇺🇸Florida Keys

Hemingway House, Key West – A Singular Structure in the Southernmost City

Well before its famous second owner happened along, the stately digs at 907 Whitehead Street stood out among all the other homes in Key West. From its construction in 1851 through to today, it remains the largest residence on the island. It also sits on the second highest elevation in all of Key West. It was that second owner, though, that gave Hemingway House its everlasting fame (and name).

Hemingway House Before Hemingway

The house was originally built by a ship’s architect/captain named Asa Tift. He moved here from Connecticut with his wife and daughter. The couple gave birth to two sons, though Mrs. Tift and their boys all passed away within three years of the Tift’s arrival in Key West.

Ernest Hemingway, his wife, Pauline, and their two sons would enjoy a more pleasant living experience here.

The Hemingway Years

The full Hemingway clan lived here from 1931–1940. The house had electricity when the Hemingway’s moved in. Plumbing, though, would not arrive until 1944. By that time Papa Hemingway had already moved on, leaving his wife and kids in the Keys on their own.

Before he left, though, Hemingway added one more unique feature to Hemingway House: the pool. At the time of its construction in 1938, it was the only swimming pool in Key West. Pools were so uncommon at the time, in fact, that you couldn’t find one within 100 miles of Hemingway House.

Emotive Architecture

The pool is incredible, as are the beautifully manicured gardens, assorted antiques, and remembrances of Hemingway. What truly strikes me about Hemingway House, though, is its architecture.

The handsome French Colonial facade would be right at home in so many of my favorite corners of the Caribbean. Fort-de-France in Martinique. Jacmel or Cap-Haitien in Haiti. Roseau in Dominica. Even select corners of Frederiksted are echoed in the ornate wrought iron, the arched windows, and double wraparound verandahs.

There’s a palpably emotive romantic air to the structure that I find intoxicating, soulful, and a little bit sad.

Just imagine the emotions Asa Tift must have grappled with, having created such an amazing home for his family only to have them die here so quickly. Tift continued to live among the stately beauty of his home for another 35 years after his wife and sons died. Those could not have been easy years, though I can’t say that I blame him for staying.

Truly, there is no place in The Florida Keys quite like Hemingway House thanks to Asa Tift… with an assist to the home’s namesake.

Uncommon Caribbean
is Steve and Patrick Bennett, two brothers from St. Croix changing the way people think about travels to the Caribbean by putting authentic aspects of island life and the region's unique cultural heritage in the spotlight ahead of the glitzy, one-size fits all tourist trap image popularized over the years. More about us

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