Truman Annex, FL
Key West
Visit Truman Annex
Stay near popular Truman Annex attractions
Things to do
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
$79
per adult
94% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
$59
per adult
94% of travellers recommend
Shipwreck Treasure Museum Tickets
$19
per adult
80% of travellers recommend
Sunset Sail in Key West with Beverages Included
$79
per adult
98% of travellers recommend
Afternoon Reef Snorkel & Catamaran Sail w/ Open Bar in Key West
$68
per adult
90% of travellers recommend
Truman Annex Hotel Deals
Weatherstation Inn
57 Front St Key West FL
$259 nightly
The price is $291 total per night from Nov 1 to Nov 2
$291 total
Nov 1 - Nov 2
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 ...
9.4/10 Exceptional! (1,002 reviews)
"Our stay was for two nights in October 2026. This is a beautiful property in a wonderful neighborhood, the Truman Annex section of Key West. The hotel is historic, quite classic, with property filled with tropical plantings, all well maintained. The staff was so friendly, professional, polite and ..."
Reviewed on Oct 17, 2026
Hyatt Vacation Club at Sunset Harbor, Key West
200 Sunset Lane Key West FL
$243 nightly
The price is $274 total per night from Oct 28 to Oct 29
$274 total
Oct 28 - Oct 29
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! (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 Oct 17, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
$265 nightly
The price is $298 total per night from Oct 20 to Oct 21
$298 total
Oct 20 - Oct 21
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 ...
8.8/10 Excellent! (1,800 reviews)
"All perfect!! Nice place"
Reviewed on Oct 18, 2026
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
$200 nightly
The price is $225 total per night from Nov 3 to Nov 4
$225 total
Nov 3 - Nov 4
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 ...
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
$175 nightly
The price is $197 total per night from Oct 25 to Oct 26
$197 total
Oct 25 - Oct 26
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! (2,739 reviews)
"This hotel is closer to the Key West airport than it is to downtown. This did not matter since the hotel is like a vacation all on its own. With 2 pools and and outdoor bars as well as games on site there is less of a need to go downtown. I arrived at the hotel before the official check in time and ..."
Reviewed on Oct 19, 2026
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
$202 nightly
The price is $227 total per night from Oct 27 to Oct 28
$227 total
Oct 27 - Oct 28
Total with taxes and fees
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. ...
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
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.
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.
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.
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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