Key West’s Famous Residents, Past and Present

Earnest Hemmingway
Ernest Hemingway Key West

Today there are about 25,000 people living in Key West. That is a lot of residents for such a tiny island, but Key West has so much to offer such as a laid back atmosphere, great fishing and diving, agreeable weather most of the year, and beautiful scenery and sunsets. So it is no wonder that so many people call Key West home. Even some celebrities have called our little piece of Paradise home, at least for awhile.

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Here is a list of some of Key West’s more famous residents, past and present… More information about them at the bottom of this page.

  • Ernest Hemingway
  • Tennessee Williams
  • Kelly McGillis
  • David Allen Coe
  • Calvin Klein 
  • Angelo Dondhia
  • Shel Silverstein
  • Judy Blume
  • David Wolkowski
  • Truman Capote
  • John Martini
  • John James Audubon
  • Mel Fisher
  • Harry Truman
  • Winslow Homer
  • Robert Frost
  • Lincoln Theodore Perry / Stepin Fetchit
  • David Robinson
  • Kenny Chesney
  • Stuart Woods

For more information about things to do and see in our island city, go to our Key West Web Site. You can also visit our Key West Events Calendar to see more details on upcoming special events.

Key West Sandbar Trips

The most relaxing way to enjoy the waters off of Key West. Get out to one of our famous sandbars on board the “Toon Time” with Toon Time Charters. Enjoy the tropics to the fullest with your toes in the sand and a drink in your hand. Affordable 2 person pricing.

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  • Ernest Hemingway – Probably the all-time most famous Key West resident, he lived here with his second wife, Pauline Pfeiffer, and their sons for most of the 1930’s. He made Key West fishing Key West visitors can check out the Hemingway Home and Museum on Whitehead Street to get a personal look at how this legend lived.
  • Tennessee Williams – This famous playwright and his partner and secretary, Frank Merlo, spent their fourteen year relationship dividing their time between New York City and 1431 Duncan Street in Key West, Florida. Now, you can check out the Tennessee Williams Museum at 513 Truman Ave, or see a play at the Tennessee Williams Theater at the Florida Keys Community College on College Road.
  • Kelly McGillis – This Top Gun actress lived in Key West with her husband and children in the 1990’s where they operated Kelly’s Caribbean on Whitehead Street (now called First Flight).
  • Jimmy Buffet – Key West is where this famed musician got his start in the music industry, supposedly playing his first gig at the Chart Room Bar at the Pier House Resort. Now, he will still visit and perform on occasion. And you can always check out his restaurant, Margaritaville, located on Duval Street.
  • David Allen Coe – This singer lived in Key West where he hung out with Shel Silverstein who encouraged him and fought with Jimmy Buffett who accused him of plagiarism.
  • Calvin Klein – Famed fashion designed once lived at 712 Eaton Street, now known by locals as the Calvin Klein house. He bought the house in 1981 for $975,000 and sold it in 1986 for just $400,000. The house just recently sold again for around $3,500,000!
  • Angelo Dondhia – Internationally famous designer that owned the Calvin Klein house before Calvin Klein. His client list included the likes of Donald Trump, Neil Simon, and Diana Ross to name just a few!
  • Shel Silverstein – “The Giving Tree” author bought his home on 618 William Street in the 1980s and lived there until his death in 1999. Unfortunately, the home was destroyed during Hurricane Irma.
  • Judy Blume – Children’s author Judy Blume spends a lot of her time in Key West. She also owns Books & Books at 533 Eaton Street. It is a very cool bookstore and Art Studio; check it out!
  • David Wolkowski – This famous developer, responsible for much of Key West’s development,  passed away at 99 years old in 2018. His most famous project was probably the building of the Pier House Resort at 0 Duval Street.
  • Truman Capote – He once rented a trailer from David Wolkowski and lived there for the entire winter while writing his novel, Answered Prayers.
  • John Martini – This artist divides his time between Key West and France. You can find his works locally at the Lucky Street Gallery.
  • John James Audubon – Naturalist that briefly lived in Key West in 1932 to study and draw birds such as the sooty tern and the brown noddy. You can now visit the Audubon House and Gardens on Whitehead Street in Key West and see some of this now famous art.
  • Mel Fisher – Famed treasure hunter that found the shipwrecked Atocha, a Spanish Galleon. You can find local jewry stores selling coins and emeralds found on the ship. And make sure to visit the Mel Fisher Maritime Museum at 200 Green Street for an interesting and informative Key West activity.
  • Harry Truman – The 33rd President of the United States spent many winters in Key West during his time in office. Now, you can visit the Harry S Truman Little White House at 111 Front Street during your visit to the island.
  • Winslow Homer – This self-taught painter spent many winters living in Florida, including Key West. His 1903 painting, Key West, Hauling Anchor beautifully portrays the blue water over sand bottom.
  • Robert Frost – starting in 1945, the poet laureate spent sixteen consecutive winters in Key West to get away from the cold New England temperatures. The house that he stayed at was owned by Jessie Porter, and until 2010 was know as the Key West Heritage House and Robert Frost Museum. Now it is privately owned, but you can still rent the house located at 410 Caroline Street through Air B&B.
  • Lincoln Theodore Perry / Stepin Fetchit – A Key West native became Hollywood’s first widely known black actor.
  • David Robinson – This award winning basketball player was actually born in Key West in 1965!
  • Kenny Chesney – Unfortunately, the famed country singer did not live here long since his address was published and he was barraged with fans trying to get near him.
  • Stuart Woods – This author of thrillers says that he likes temperatures around 70 degrees, so in 2004 he bought a home in Key West where he spends part of the year.

These are the names of the residents that truly put Key West on the map. One of many reasons people Visit Key West to explore our rich history.

About the author: Island Genn

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