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 ฿5,884 per night from 23 Aug to 24 Aug
฿5,884
per night
23 Aug - 24 Aug
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! (1,002 reviews)
"Nice place"

Reviewed on 15 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
The price is ฿7,550 per night from 3 Sept to 4 Sept
฿7,550
per night
3 Sept - 4 Sept
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! (414 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 17 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 ฿4,535 per night from 3 Sept to 4 Sept
฿4,535
per night
3 Sept - 4 Sept
Stay at this spa 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! (3,544 reviews)
"Great location. Clean rooms. Very pleased with the hotel."

Reviewed on 20 Aug 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 ฿3,530 per night from 26 Aug to 27 Aug
฿3,530
per night
26 Aug - 27 Aug
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! (2,349 reviews)
"Staff was nice"

Reviewed on 19 Aug 2026

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 ฿4,734 per night from 9 Sept to 10 Sept
฿4,734
per night
9 Sept - 10 Sept
Stay at this business-friendly hotel in Key West. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,858 reviews)
"Very good 😊"

Reviewed on 19 Aug 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 ฿3,845 per night from 1 Sept to 2 Sept
฿3,845
per night
1 Sept - 2 Sept
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 ...
8.6/10 Excellent! (2,638 reviews)
"This place was really nice. It was very clean and quiet. The staff is very helpful and friendly. We enjoyed the outdoor pools, food and bar. There is lots of activities outside to do with your family and friends. We didn’t have a problem at all while we stayed there. I would definitely stay there ..."

Reviewed on 19 Aug 2026

Blue Flamingo Resort Key West
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