Truman Annex, FL

Key West

A large, colorful marker labeled 'Southernmost Point' with a view of the ocean and a clear sky in the background.
A white building with American flags and a sign for 'Harry's Truman Overseas Hotel'.
A series of tall, slender poles against a clear blue sky.
A large red brick building with arched windows and a tiled roof, surrounded by palm trees.
A sunset over a calm sea with a pier extending into the water.

Stay near popular Truman Annex attractions

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.

Harry S. Truman Little White House

9.0/10 (995 reviews)
Visit the winter home of President Harry S. Truman to see where some of America’s most important post-war decisions were made.
See properties

Things to do

Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

$79
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
Key West Champagne Sunset Sail

Champagne and Sunsets: A Key West Catamaran Adventure

$59
per adult
94% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included

$79
per adult
98% of travellers recommend
Sunset Sail in Key West with Beverages Included
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

$41
per adult
88% of travellers recommend
Key West Conch Tour Train
Entertainer in character at the Shipwreck Treasure Museum in Key West

Shipwreck Treasure Museum Tickets

$19
per adult
80% of travellers recommend
Shipwreck Treasure Museum Tickets
Afternoon Key West Reef Snorkel & Catamaran Sail

Afternoon Reef Snorkel & Catamaran Sail w/ Open Bar in Key West

$68
per adult
90% of travellers recommend
Afternoon Reef Snorkel & Catamaran Sail w/ Open Bar in Key West
See all activities in Key West

Truman Annex Hotel Deals

Weatherstation Inn

Weatherstation Inn

2.5 out of 5
57 Front St Key West FL
The price is $291 total per night from Nov 1 to Nov 2
$291 total
per night
Nov 1 - Nov 2
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 ...
9.4/10 Exceptional! (1,001 reviews)
"Les portes étaient noires tout autour des poignées les céramiques de la salle de bain sales très très déçu de cette chambre"

Reviewed on Oct 13, 2026

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
The price is $273 total per night from Oct 28 to Oct 29
$273 total
per night
Oct 28 - Oct 29
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! (437 reviews)
"Had an excellent time. Absolutely beautiful hotel and amazing staff!"

Reviewed on Oct 8, 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
The price is $298 total per night from Oct 18 to Oct 19
$298 total
per night
Oct 18 - Oct 19
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 ...
8.8/10 Excellent! (1,802 reviews)
"The smell from the seaweed was disgusting !!!"

Reviewed on Oct 14, 2026

Margaritaville Beach House Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
The price is $197 total per night from Oct 25 to Oct 26
$197 total
per night
Oct 25 - Oct 26
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 ...
8.6/10 Excellent! (2,726 reviews)
"This hotel campus was perfect for our stay. There are 2 pools and lots of activities for the kiddos. Definitely family friendly which can be tricky in the keys. Free shuttle got us to and from Duval street. Wpuld stay there again."

Reviewed on Oct 14, 2026

Blue Flamingo Resort Key West
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
The price is $227 total per night from Oct 27 to Oct 28
$227 total
per night
Oct 27 - Oct 28
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
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
The price is $246 total per night from Nov 1 to Nov 2
$246 total
per night
Nov 1 - Nov 2
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
See all 2,707 properties in Truman Annex
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
A large red brick building with arched windows and a prominent entrance.

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.

The Monroe County Courthouse with a clock tower, surrounded by trees and a clear blue sky.

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.

A white lighthouse surrounded by lush greenery and a white picket fence.

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.

A row of pastel-colored houses with white railings and a clear blue sky.

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

Choose one or more items to build your trip:

Explore a world of travel with Expedia