12 Vintage Photos of Key West, Florida from the 1900s -1980s

Key West, FL Through the Years

Key West first belonged to the Calusa and Tequesta peoples before Juan Ponce de León arrived in 1513, dubbing it “Cayo Hueso” (Bone Island).

By the 1850s, the island had transformed into America’s richest city per capita through its shipwreck salvaging boom.

Today, it’s one of the most popular vacation spots in the US, with a history just as colorful as its pastel-hued houses.

A wagon driving by the San Carlos building on Duval Street, circa 1905

In the early 1900s, horse-drawn wagons  were the main way to get around Key West. This one is passing by the San Carlos Institute.

Built in 1871 by Cuban exiles on Duval Street, IT was one of America’s first bilingual and integrated schools.

The building became an important cultural center where Cuban independence leader José Martí gave speeches, and where students of all races studied together in both English and Spanish.

A Key West Fire Department steamer at the fire well on Whitehead Street, circa 1900s

You’re looking at the fire well behind the Monroe County courthouse, which supplied water to Key West’s steam-powered fire engines.

These coal-fired engines could pump 600 gallons of water per minute, protecting both the courthouse – with its impressive 100-foot clock tower – and the surrounding wooden buildings.

The city bought these powerful engines after a devastating fire in 1886, replacing the basic equipment used by volunteer firefighters since 1834.

Captain Carey Jack in front of the Key West Fire Department at 12th Street, circa 1900s

In that photo is a motorized American LaFrance fire engine. The Key West Fire Department received its first one in 1941.

Before that, firefighters relied on horse-drawn fire engines that used steam-powered water pumps. The indoor coal pit they used is displayed at the Key West Firehouse Museum.

They bought its first fire truck in 1953: an International R185-6 with a powerful pump that cost $12,000.

Children riding Monroe County school buses, circa 1920s

Before school buses came to Monroe County, students walked or rode horses to their one-room schoolhouses. The first student transport vehicles were horse-drawn carriages called “kid hacks” with simple wooden benches.

In the 1920s, these were replaced by motorized trucks with enclosed seating, though they were still far from modern school buses.

During this time, Key West’s power came from the Key West Gas and Electric Company, which the city bought and renamed City Electric System in 1943.

A building at 1001 Truman Avenue with a Land O’ Sun shop, circa 1940s

In the 1940s, Land O’ Sun dairy opened a shop at 1001 Truman Avenue in Key West, bringing its Tennessee-based brand to the island.

The shop served as both a milk distributor and an ice cream parlor, opening just as America’s love for ice cream exploded after wartime dairy rationing ended.

By 1946, Americans were eating over 20 quarts of ice cream per person annually, and shops like Land O’ Sun became community gathering spots where people celebrated post-war prosperity over sundaes and milkshakes.

The Gardner Pharmacy on 1114 Truman Avenue, circa 1940

There were only six civilian doctor in Key West by the time the Gardner Pharmacy was established by a family who migrated from western Kentucky.

Gardner’s pharmacists not only dispensed modern medicines but also practiced traditional folk remedies using local plants like Aloe vera and gumbo limbo bark.

Like many pharmacies of the 1940s, Gardner Pharmacy also sold an eclectic mix of products including toiletries, cosmetics, hot water bottles, hair pins, curlers, stockings, cigarettes, and candy

A store on 423 Duval Street, circa 1949

In that photo as well are two sailors: one leaning again a storefront and another entering the snack bar. They were a common sight during this time in Key West, which was a vital military asset during that period.

Key West’s location between the Gulf of Mexico and the Atlantic Ocean allowed the Navy to monitor and control ship traffic between these waters.

And being just 90 miles from Cuba, Key West was also an excellent vantage point for monitoring activity in the Caribbean, which became especially important during the Cold War.

And ad for Kiwanis Old Time Movies painted on a car, circa 1950

In 1950s Key West, the Kiwanis Club turned cars into moving billboards by painting ads on them to promote their events. Their popular “Old Time Movies” showed silent films and early talkies with live music.

Using cars as moving billboards was a clever choice for the 1950s, when automobiles were still viewed as quite the status symbols.

Sloppy Joe’s Bar at 201 Duval Street, circa 1950s

Sloppy Joe’s Bar got its name from Ernest Hemingway, who suggested naming it after a Havana bar known for its wet floors from melting ice.

The bar started as a speakeasy called the “Blind Pig” during Prohibition. When the rent went up in 1937, owner Joe Russell and his customers carried everything to a new location overnight.

By the 1950s, with its Cuban tiles and special doors, it had become a popular hangout for writers and artists following in Hemingway’s footsteps.Retry

Carolyn Gorton Fuller posing in front of her Bottle Wall, taken on November 1988

Artist Carolyn Gorton Fuller built Key West’s famous Bottle Wall at Angela and Margaret Streets when officials wouldn’t give her a stop sign for the dangerous intersection.

The wall became so beloved that the Historic Architecture Review Commission granted her special permission to keep it.

In 1991, Fuller carefully took down the wall – not angrily destroying it as local rumors claimed – and used its materials to create a new piece called “Ripples and Reflections.”

Fun fact:

She held several degrees from institutions like the University of Oregon (Master’s in painting and sculpture), Syracuse University, the Chicago Art Institute, and the University of Mexico.

Inside the Kino Sandal Factory, taken on December 1988

The Kino Sandal Factory’s story began with a dramatic escape to freedom when Roberto “Kino” López fled from Cienfuegos, Cuba in 1965.

When he first established his sandal factory in 1966, he started with just a $3,000 in savings and a $7,000 bank loan, initially operating from 105 Whitehead Street before moving to its current location at Greene and Fitzpatrick Streets in 1976.

The Bull and Whistle Bar at 224 Duval Street, taken on January 1989

The Bull and Whistle Bar building on Duval Street began as a boarding house in the early 1900s before becoming a brothel, then a Prohibition-era speakeasy.

By 1989, it had evolved into a unique three-story bar. The Bull offered live music on the ground floor.

The Whistle featured pool tables on the second floor with its New Orleans-style iron balcony, and the Garden of Eden operated as a clothing-optional rooftop bar.