Truman Annex

Key West

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.
A tree-lined sidewalk with a white picket fence and lush greenery.

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

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $63
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

CA $78
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Snorkler waving underwater in Key West

Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch

CA $85
per adult
86% of travellers recommend
Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch
Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

CA $111
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

CA $63
per adult
88% of travellers recommend
Key West Conch Tour Train
Combo image of activity in Key West

Key West Rum & Reggae: Snorkel & Sunset Sail Combo

CA $96
per adult
88% of travellers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
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 CA $246 per night from Aug 25 to Aug 26
CA $246
CA $277 total
Aug 25 - Aug 26
includes taxes & 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 ...
9.4/10 Exceptional! (1,003 reviews)
"Nice place"

Reviewed on Aug 15, 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 CA $285 per night from Sep 3 to Sep 4
CA $285
CA $367 total
Sep 3 - Sep 4
includes taxes & 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! (415 reviews)
"Make sure to unload your luggage before parking. The garage is across the street and there is no elevator. Also, I was not aware that they charge you $40 a night to park. I would also recommend calling before your arrival and confirming your stay. My Hotels app had me arriving Friday and checking ..."

Reviewed on Aug 17, 2026

Hyatt Vacation Club at Sunset Harbor, Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
The price is CA $186 per night from Sep 3 to Sep 4
CA $186
CA $310 total
Sep 3 - Sep 4
includes taxes & fees
Book a stay at this spa hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.8/10 Excellent! (3,565 reviews)
"The pool had fun activities all the days we were there. The food was really good at the restaurant on site."

Reviewed on Aug 24, 2026

Southernmost Beach Resort and Guesthouses
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
The price is CA $132 per night from Aug 25 to Aug 26
CA $132
CA $193 total
Aug 25 - Aug 26
includes taxes & fees
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the pool in our reviews. ...
Ibis Bay Beach Resort
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
The price is CA $198 per night from Sep 8 to Sep 9
CA $198
CA $310 total
Sep 8 - Sep 9
includes taxes & 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 ...
9/10 Wonderful! (1,866 reviews)
"Beautiful place I will go back"

Reviewed on Aug 24, 2026

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
The price is CA $160 per night from Aug 25 to Aug 26
CA $160
CA $257 total
Aug 25 - Aug 26
includes taxes & 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
See all 2,678 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.
A white lighthouse with a small adjacent building, surrounded by lush green trees and a clear blue sky.

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.
A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.

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 two-story house with green shutters and a wooden balcony.

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 Key West Tropical Forest and Botanical Garden.

Truman Annex

Choose two or more items and save on your trip: