Key West : Florida


What It Is Like to Retire in Key West

Key West, Florida is an extremely charming community, the southernmost in the U.S. Many active adults choose this city and island 90 miles north of Cuba as their retirement community because of its sub-tropical warmth, its diversity (home to many gays), and its laid-back charm. Key West offers a cross between a Caribbean island and an affluent U.S. tourist destination. It became the Conch Republic when the town tried to secede from the U.S.

Key West goes back before Matthew Perry planted the U.S. flag in 1822. The Old Town is famous for its gracious colonial homes and its long Duval Street, a more charming version of New Orleans’ Bourbon Street. Restaurants, shops, and bars abound. Ernest Hemingway wrote almost half of his major works from his mansion near the lighthouse, both of which can toured. Locals, referred to as “Conchs”, and tourists celebrate each night by viewing the sunset from Mallory Square at the edge of Old Town.  The newer (lower) parts of town were hard hit in 2005 by Hurricane Wilma.  Cars are not necessary in Key West. Just about everybody gets around on a 50's style "cruiser", big fat-tired bikes that can go over curbs and cart the groceries..

Where to Retire in Key West and Home Prices

People live in private homes and condominiums in many different neighborhoods - either in Old Town in quiet neighborhoods, or along the ocean.  The Truman Annex looks out over the water and the cruise ship terminal. This luxurious gated community, the former U.S. Naval Base, has many homes and condos. The “Truman White House” is in this complex, where Harry S. used to vacation. Yet some retirees of limitied means spend time here in the winter using creative strategies - staying in RV parks (the military has 2 subsidized ones), timeshares, or staying up island.
Real estate is quite expensive, having recovered from the recent recession.  Legions of dilapidated hulks in Old Town lhave been restored into island masterpieces, complete with old fashioned hurricane shutters and wide porches. There are many homes for sale in the millions of $'s. The median home value was $945,622 in early 2022, a 31% rise over the past year, according to Zillow.


What Is Special about Key West

• Fort Zachary Taylor National Park (and great beach) • Unusual Key West cemetery • Mallory Square and evening sunsets • Sloppy Joe’s bar, a Hemingway hangout • Old Town • Beautiful old island houses • Beaches • No car needed • Key West Golf Club and residential community • Key West Old Island Days • World class fishing •Take the Key West Quiz!

What Is Not Special about Key West

Hurricane season. Masses of cruise ship passengers disembarking and getting rowdy on Duval Street.

Who Will Like Retirement in Key West

Just about anyone who likes a casual lifestyle and a diverse community. Here are more resources and information on what is like to retire in Florida.

Local Economy Is Driven by

Tourism, snowbirds, fishing, boating, and cruise ship passengers at the bars.

Climate and Physical Environment

This is an island and the southernmost point in the continental U.S. Key West is the last "key" in the Florida Keys that extend south from Miami (about 121 miles). It is about 98 miles north of Cuba. Key West Island is about 4 miles by 2 miles, the City also comprises parts of other small islands. At its tip the Atlantic Ocean and Gulf of Mexico are joined.

Restaurants & Cultural Scene

• The Tennessee Williams Theatre is a performing arts center  • The Key West Symphony performs here to great reviews • The Key West Literary Seminar celebrates writers and writing each January. An international audience comes to hear such writers as Ian McEwan, and Joyce Carol Oates. • The Key West Botanical Forest and Garden • See 24 Hours in Key West • Duval Street has many bars, restaurants, and entertainment options. • Many artists and writers live here. There are 2 theatres that put on interesting plays.



Key West has some tourist related crime. People out partying at 2 in the morning get into all kinds of trouble. There is a large homeless population which is sometimes accused of being behind the major crime problem in Key West - stolen bikes. But it doesn't matter who is stealing them, lock up your bike!

Medical Facilities

Lower Keys Medical Center. Fishermen's Hospital is in Marathon, about 54 miles.


The great thing about Key West is, once you get here, there is no need for a car. Key West International Airport is very convenient to town. Driving by car down Rt 1 to get here from the mainland is arduous, but interesting.  A cruiser bike or a good pair of walking shoes are the best way to get around. 

Valuable Links

Key West

Key West on Wikipedia


What people are saying about Key West

Put me down for Key West
What a great place. Warm, lots to do, great restaurants. It's only drawback is it is expensive. But boy are there some nice places to live. Bring your bike and park your car away.
Posted by ctyankee on March 16, 2007

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