The Truman Annex: Presidential History & Manicured Lawns

For over 125 years, the Truman Annex was a restricted federal military installation. During the Civil War, Union naval forces used the base to blockade Confederate shipping; during the Spanish-American War, the battleship USS Maine sailed from these very piers toward her doom in Havana Harbor.

Between 1946 and 1952, President Harry S. Truman transformed the commanding officer's quarters into a functional winter White House. Key West offered Truman both restorative sunshine and the security of a naval base. Here he formulated the Truman Doctrine, met with the Joint Chiefs of Staff, and signed historic executive orders desegregating the armed forces. Other presidents who used the residence include Taft, Eisenhower, Kennedy (during the Cuban Missile Crisis), Carter, and Clinton.

At the southern end of the Annex lies the 66-acre Truman Waterfront Park, created on reclaimed military harbor lands. This modern municipal park is an extraordinary community asset: it features a colorful interactive water splash pad for toddlers, a modern children's playground, wide paved walking and rollerblading paths, and a weekly Thursday evening Farmers Market.

The park is also home to the Coffee Butler Amphitheater, an open-air 4,000-capacity concert venue overlooking the Gulf of Mexico where top national musical acts perform against sunset backdrops.

For travelers seeking quiet residential luxury without leaving Old Town, the Truman Annex is the premier vacation rental community on the island. Many historic naval barracks and officer quarters have been converted into two- and three-bedroom condominiums and townhomes with private community swimming pools.

Because non-resident vehicle traffic is banned, the streets are remarkably peaceful—with zero late-night bar noise, minimal traffic, and shaded brick lanes where children can safely ride bicycles. You are an 8-minute walk from Mallory Square and Duval Street, yet in an atmosphere of complete residential tranquility.