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.
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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
7 mile bridge and the Overseas Highway

Miami to Key West Day Trip with Activity Options

$49
per adult
84% of travellers recommend
Miami to Key West Day Trip with Activity Options
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
$219 nightly
The price is $246 total per night from Nov 11 to Nov 12
$246 total
Nov 11 - Nov 12
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
Fully refundableReserve now, pay when you stay
$206 nightly
The price is $232 total per night from Nov 18 to Nov 19
$232 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! (444 reviews)
"Not was we expected."

Reviewed on Nov 5, 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
$226 nightly
The price is $319 total per night from Nov 30 to Dec 1
$319 total
Nov 30 - Dec 1
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
$200 nightly
The price is $225 total per night from Nov 29 to Nov 30
$225 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
$175 nightly
The price is $197 total per night from Nov 15 to Nov 16
$197 total
Nov 15 - Nov 16
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 ...
8.6/10 Excellent! (2,783 reviews)
"The room was clean & comfortable and had a waterfront view but you had to look past the hustle & bustle of US 1. The room was surprisingly quiet given the road noise. The resort was charming and had 2 pools. Resort could provide some more pool floaties for those that love relax in the pool. Perhaps ..."

Reviewed on Nov 9, 2026

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. ...
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Beachside Resort & Residences
See all 2,704 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

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