Truman Annex Travel Guide

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 £168 per night from 25 Oct to 26 Oct
£168
25 Oct - 26 Oct
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! (1,004 reviews)
"This place is excellent. Very quiet. Nice amenities. Close to old town"

Reviewed on 20 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 £205 per night from 28 Oct to 29 Oct
£205
28 Oct - 29 Oct
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! (438 reviews)
"The room was ok. They charged us a $30 a day ($210) resort fee but never told us what if anything it included. We had to beg to get beach towels. They have a continental breakfast one day a week from 8 to 9. By 8:20 they were out of food and never replenished it. There weren’t any dining/drink options ..."

Reviewed on 17 Oct 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
The price is £233 per night from 25 Oct to 26 Oct
£233
25 Oct - 26 Oct
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 ...
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 £193 per night from 21 Oct to 22 Oct
£193
21 Oct - 22 Oct
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 ...
9/10 Wonderful! (1,889 reviews)
"IMPROVE THE LOBBY. TOO MANY HALLOWEEN DECORATIONS."

Reviewed on 20 Oct 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 £140 per night from 28 Oct to 29 Oct
£140
28 Oct - 29 Oct
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! (2,742 reviews)
"Absolutely loved this hotel!!! Can’t wait to come back again. The staff was so friendly and helpful, the room was clean and the property was so nice. The whole property is wheelchair accessible, my room was on the ground floor so very easy to access. Loved how accommodating the staff was and how ..."

Reviewed on 20 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
The price is £171 per night from 21 Oct to 22 Oct
£171
21 Oct - 22 Oct
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! (2,633 reviews)
"Our room was a king suite with pool access and it was beautiful! The only negative was the air conditioner would not cool the room below 73, which was too warm for us. No maintenance came to look at it either. We were disappointed that the hot tub by the pool didn’t work either. After a long flight ..."

Reviewed on 20 Oct 2026

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. Learn more about Truman Annex
Learn more about Truman Annex

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.

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.

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.



Truman Annex Travel Guide

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