Truman Annex Travel Guide

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

Things to do


Top hotels in Truman Annex

Weatherstation Inn

Weatherstation Inn

2.5 out of 5
57 Front St Key West FL
The price is ฿5,918 per night from 11 Aug to 12 Aug
฿5,918
฿6,658 total
11 Aug - 12 Aug
includes taxes & fees
Stay at this boutique B&B in Key West. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in their reviews. ...
9.4/10 Exceptional! (1,008 reviews)
"Weather Station Inn built in 1911, so have to recognize old building. However, our room on second floor, and stairs to second floor, could use some maintenance. Our room, Grand Bahama, was big and nice, but very sparse in decorative items. Wooden floor in places needed repairs and a few nice area ..."

Reviewed on 10 Aug 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
Fully refundableReserve now, pay when you stay
The price is ฿8,308 per night from 10 Sept to 11 Sept
฿8,308
฿10,462 total
10 Sept - 11 Sept
includes taxes & fees
Stay at this hotel in Key West. Enjoy free Wi-Fi, parking (surcharge) and concierge services. Popular attractions Duval Street and Mallory Square are located ...
8.6/10 Excellent! (409 reviews)
"Very nice"

Reviewed on 7 Aug 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 ฿4,561 per night from 1 Sept to 2 Sept
฿4,561
฿7,549 total
1 Sept - 2 Sept
includes taxes & fees
Stay at this beach hotel in Key West. Enjoy free Wi-Fi, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their reviews. ...
8.8/10 Excellent! (3,500 reviews)
"Phenomenal stay! Gorgeous views and amenities. Staff was so attentive and went above and beyond for everything. Will absolutely be coming back!"

Reviewed on 10 Aug 2026

Southernmost Beach Resort and Guesthouses
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
The price is ฿3,527 per night from 11 Aug to 12 Aug
฿3,527
฿7,129 total
11 Aug - 12 Aug
includes taxes & fees
Stay at this beach hotel in Key West. Enjoy free Wi-Fi, 2 restaurants and a private beach. Our guests praise the pool and the helpful staff in their reviews. ...
8.6/10 Excellent! (2,418 reviews)
"It was a great place, the furniture and deco very nice and high end, the shuttle to downtown a big plus. The beach OK, but you must realize that you don't go to Key West for the beach, you go for the environment in town, the people, the shopping, the food and the most amazing sunset."

Reviewed on 10 Aug 2026

Beachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
The price is ฿3,990 per night from 9 Sept to 10 Sept
฿3,990
฿6,349 total
9 Sept - 10 Sept
includes taxes & fees
Stay at this family-friendly hotel in Key West. Enjoy free Wi-Fi, 2 outdoor pools and 2 restaurants. Our guests praise the pool and the helpful staff in their ...
Blue Flamingo Resort Key West
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
The price is ฿3,749 per night from 11 Aug to 12 Aug
฿3,749
฿5,284 total
11 Aug - 12 Aug
includes taxes & fees
Stay at this beach hotel in Key West. Enjoy free breakfast, free Wi-Fi and a private beach. Our guests praise the breakfast and the pool in their reviews. Popular ...
8.2/10 Very good! (2,347 reviews)
"Nice property. Didn't love that it was on a busy street but overall a great place to stay. Not close to downtown but if you rent a golf cart it's no problem."

Reviewed on 10 Aug 2026

Ibis Bay Beach Resort
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 for the activities you enjoy most.

Old Town Key West

While visiting Old Town Key West, you might make a stop by sights like Duval Street and Florida Keys Beaches.

Downtown Key West

While visiting Downtown Key West, you might make a stop by sights like Duval Street and Ernest Hemingway Home and Museum.

Key West Historic District

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

New Town

While there might not be top attractions in New Town, you can explore the larger area and discover places like Smathers Beach and Key West Tropical Forest and Botanical Garden.



Truman Annex Travel Guide