Truman Annex

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

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 HK$1,953 per night from 2 Nov to 3 Nov
HK$1,953
HK$2,198 total
2 Nov - 3 Nov
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! (1,001 reviews)
"This was the perfect location for access to Key West by foot!!!! We loved the community the resort is in!"

Reviewed on 26 Oct 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 HK$2,084 per night from 18 Nov to 19 Nov
HK$2,084
HK$2,610 total
18 Nov - 19 Nov
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 ...
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 HK$1,797 per night from 18 Nov to 19 Nov
HK$1,797
HK$2,518 total
18 Nov - 19 Nov
includes taxes & fees
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 in ...
8.8/10 Excellent! (1,800 reviews)
"Perfect beach view from the room."

Reviewed on 29 Oct 2026

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
The price is HK$1,130 per night from 19 Nov to 20 Nov
HK$1,130
HK$1,769 total
19 Nov - 20 Nov
includes taxes & fees
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 ...
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 HK$981 per night from 1 Nov to 2 Nov
HK$981
HK$1,546 total
1 Nov - 2 Nov
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 ...
8.6/10 Excellent! (2,757 reviews)
"I went to the desk to check in. They said your room is ready. They said you can wait to check in or pay $35 to check in now. It was 3:00 so they wanted me to pay $35 to check in an hour early. It’s bad enough the fees were $80 but now they charge you to check in your room"

Reviewed on 29 Oct 2026

Blue Flamingo Resort Key West
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
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. ...
Beachside Resort & Residences
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 Fort East Martello Museum and Gallery.



Truman Annex