Truman Annex, FL

Key West

A historical marker for The Little White House.
A large, colorful marker labeled 'Southernmost Point' with a view of the ocean and a clear sky in the background.
A historical marker for The Little White House, built in 1890, used by American Navy officers, and listed on the National Register of Historic Places in 1974.
A red brick building with arched windows and a red roof, surrounded by palm trees.
A white house with red and white flags, surrounded by lush greenery and palm trees.

Spend time in Truman Annex to discover local landmarks, engaging museums, and family-friendly beaches across unique neighborhoods.

Truman Annex is an ideal destination for city and family travelers. You can explore nearby attractions such as Duval Street, a bustling street known for its vibrant atmosphere, and the Southernmost Point, a symbolic landmark that marks the southernmost tip of the continental United States. Also, visit Mallory Square, a modern square famous for its sunset celebrations. For activities, nearby venues like Papa's Pilar Rum Distillery offer insights into local rum production, while the Waterfront Playhouse and Red Barn Theater provide theater experiences. Nature enthusiasts can enjoy the nearby Florida Keys, Fleming Key, and Stock Island, each known for their beaches and outdoor tourism.

Spend some time exploring the different neighborhoods surrounding Truman Annex. Nearby, Old Town Key West is known for family experiences, featuring Clarence S. Higgs Memorial Beach Park and the Mel Fisher Maritime Museum. Another area, the Key West Historic District, offers cultural insights through spots like the Key West Shipwreck Museum and Audubon House and Tropical Gardens. Downtown Key West also caters to city and family experiences, with attractions such as the Florida Keys National Marine Sanctuary and Truman Beach. Each neighborhood has its own unique character and places to discover.

The best time to visit Truman Annex aligns with the warm months from June to September, when temperatures range from 83 to 84°F and the weather is mostly dry and sunny. While the destination remains popular year-round, it tends to be a bit quieter in August and during October to November. This means you can enjoy the attractions and natural features with fewer crowds during those times, making it a pleasant experience for visitors.


Stay near popular Truman Annex attractions

Things to do


Truman Annex Hotel Deals

Weatherstation Inn

Weatherstation Inn

2.5 out of 5
57 Front St Key West FL
$199 nightly
The price is $224 total per night from Nov 29 to Nov 30
$224 total
Nov 29 - Nov 30
Total with taxes and fees
Book a stay at this boutique B&B in Key West. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
Weatherstation Inn
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
200 Sunset Lane Key West FL
$208 nightly
The price is $234 total per night from Nov 18 to Nov 19
$234 total
Nov 18 - Nov 19
Total with taxes and fees
Stay at this hotel in Key West. Enjoy free WiFi, parking (surcharge), and concierge services. Popular attractions Duval Street and Mallory Square are located ...
8.6/10 Excellent! (445 reviews)
"This resort is amazing. Absolutely prime location within a few minutes walking distance to Mallory square, duval street and the Truman annex. The resort is older but it is well kept. Highly recommended."

Reviewed on Nov 11, 2026

Hyatt Vacation Club at Sunset Harbor, Key West
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
$285 nightly
The price is $321 total per night from Nov 18 to Nov 19
$321 total
Nov 18 - Nov 19
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the pool and the restaurant ...
Margaritaville Beach House Key West
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
$171 nightly
The price is $192 total per night from Nov 29 to Nov 30
$192 total
Nov 29 - Nov 30
Total with taxes and fees
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...
Havana Cabana at Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
$166 nightly
The price is $187 total per night from Nov 16 to Nov 17
$187 total
Nov 16 - Nov 17
Total with taxes and fees
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Blue Flamingo Resort Key West
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
Beachside Resort & Residences
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Where to stay in Truman Annex

Find the best Truman Annex areas and neighborhoods for the activities you enjoy most. Learn more about Truman Annex
Learn more about Truman Annex

Old Town Key West

If you're spending some time in Old Town Key West, Duval Street and Florida Keys Beaches are top sights worth seeing.

Downtown Key West

If you're spending some time in Downtown Key West, Duval Street and Ernest Hemingway Home and Museum are top sights worth seeing.

Key West Historic District

Travelers to Key West Historic District praise its fantastic nightlife. If you've got some more time to explore, be sure to make a stop by Duval Street and Florida Keys Beaches.

New Town

Though New Town might not have many top sights, you can venture to the surrounding area to see attractions like Smathers Beach and Fort East Martello Museum and Gallery.



Truman Annex, FL

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