Few neighborhoods in Key West carry as much history as Truman Annex. Tucked along the northwest corner of the island, this 103-acre community sits on land that was once one of the most strategically important naval installations in the United States. Today, it is one of Key West’s most desirable and beautiful residential enclaves, blending a fascinating past with an enviable island lifestyle.
The History of Truman Annex
The land that makes up Truman Annex was originally part of the Naval Air Station Key West, established in 1823 as the U.S. Navy’s southernmost base. For well over a century, the base played a critical role in American military history, from the Civil War and the Spanish-American War through both World Wars and the Cold War. The Navy’s presence shaped Key West in profound ways, bringing infrastructure, jobs, and a steady stream of activity to the island.
Perhaps the most famous chapter of the base’s history involves President Harry S. Truman, who used the commandant’s quarters as a working vacation retreat. He visited 11 times during his presidency, logging 175 days at what became known as the Harry S. Truman Little White House. Other presidents, including Eisenhower and Kennedy, also spent time on the property. The Little White House still stands today and is open to the public for guided tours.
From Base to Neighborhood
When the Navy began decommissioning portions of the base in the late 1980s, a developer purchased the land and transformed it into the residential community that exists today. The redevelopment focused on preserving the neighborhood’s historic architecture while adding new homes and amenities. The result is a thoughtfully planned community featuring beautifully maintained Victorian-style homes, lush landscaping, gated security, and easy access to the waterfront.
Truman Annex Today
Today, Truman Annex has a character that feels distinct from the rest of Key West. The streets are quiet and walkable, lined with mature trees and charming homes that reflect the island’s architectural heritage. Residents and visitors are just a short walk away from Fort Zachary Taylor Historic State Park, home to one of the best beaches in Key West. The beautifully redone Truman Waterfront Park and Florida Keys Eco-Discovery Center are additional attractions within easy reach.
Truman Annex Vacation Rentals
There is no better way to experience Truman Annex than staying right in the neighborhood. At Compass Realty, we offer vacation rentals in Key West, including Truman Annex. Our Truman Annex rentals put you steps from historic landmarks, beautiful beaches, and Key West’s most walkable streets.
Whether you are planning a romantic getaway or a family trip, our properties give you a true sense of island living in one of Key West’s most storied communities. Browse our available rentals or call us at 305-292-1881 to find the perfect fit for your stay.
