If you are planning a Key West Vacation, you might be wondering about about Key West vacation rentals in Truman Annex Key West.
While Key West is well known as the Southernmost point of the US for the bars and restaurants along Duval Street, world class fishing and nightlife party scene, there is so much more to do!

Truman Annex Key West
Pet Friendly Key West a tiny city so full of history that it is a must visit spot for United States history buffs!
Originally a U.S. Army installation, the Truman Annex Key West FL neighborhood then became a naval station, serving the country during the Spanish-American War through World War II. Whether you are a history buff or a beach lover looking for Key West rentals on beach, Key West has something for everyone!
The History of Truman Annex in Key West
Truman Annex was founded in 1845 as a military stronghold to safeguard shipping lanes between the Atlantic Seaboard and Gulf of Mexico from pirates. Its primary purpose was to ensure safe passage of ships before and during the Civil War.
If you aren't familiar with the history of Key West, you're in for a treat! Key West was essentially founded by pirates, as the rocky coral hammock off the coast of Key West was a prime area for shipwrecks.
There is even a Key West Shipwreck Museum near Mallory Square that tells the history of pirating on the island.
The history of the US Navy in Key West
Due to its strategic location near Cuba, and in the middle of World War I, the U.S. Navy had to relocate their entire naval fleet to Key West. Following World War I, the base was decommissioned, military housing Key West closed and all personnel were either transferred to other bases or released from service.
The majority of the buildings in what is now known as Key West rentals Truman Annex were dismantled and relocated to other sites. The United States Navy still owns 17 acres, providing the military lodging Key West visiting service members need while visiting the base. Like the Naval Lodge Key West!
Harry Truman Key West White House
The Harry Truman House Key West, known as the Harry Truman Little White House, is one of the main tourist attractions in historic Key West.
Located in the quaint neighborhood of the Annex in Old Town Key West, the Little White House was President Harry S. Truman's winter retreat for 11 visits and a total of 175 days! Oceanfront Key West rentals were ALWAYS in high demand - even by President Truman!
Quoted in “Truman, Barkley Turn to Changes,” New York Times, November 11, 1948, it was been verified that Harry Truman visited the island of Key West 11 times from November 1946 to March 1952.
Of course, we wouldn't expect a United States President to to stay in Key West condominium rentals, would we? Even oceanfront condos in Key West Florida would not be safe - or dignified - for a standing US President!
Harry Truman both vacationed and worked at the property, which is why they call it the Little White House. You can book tickets to tour the Little White House here.
Truman Annex Key West Rentals
The most expensive neighborhoods in Key West are The Meadows, Old Town, Casa Marina and of course, the Annex. The Meadows is the smallest of these areas. In the late 1800's and early 1900's, The Meadows were merely a grassland area.
If you are planning a vacation to Key West for one of the many exciting Key West Events, you can find lots of options for VRBO Key West, Key West condo rentals, of course, Key West Truman Annex Rentals.
If you would like ideas for things to do in Key West or the upper Florida Keys, check out some of our helpful Travel Tips for the Florida Keys! Just be aware of the Key West beach rules before hitting the water!
Travel Tips Florida Keys
- Key West BrewFest Events ‘On Tap’ Aug. 29 Through Sept. 2
- Conch Republic Independence Celebration
- Book a Key Largo Snorkeling Tour
- Where to Stay in the Florida Keys The Winter Season
Where to stay in Key West
Aside from hotels in Truman Annex Key West, you also have some other options:
Truman annex condominium rentals - click here to find condo rentals in Key West through Expedia
Truman Annex shipyard condos - click here to find Shipyard Condos Key West
Navy Key West vacation rentals - click here to find Key West vacation rentals near the Navy base
Key West condominium rentals
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