Truman Annex Holidays
Book a Hotel + Flight or Car together to unlock savings
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
Old Town Key West
4 out of top 10 points of interest in this area
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
2 out of top 10 points of interest in this area
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.
Uptown - Upper Duval
If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.
Top hotels in Truman Annex
Weatherstation Inn
57 Front St Key West FL
Fully refundableReserve now, pay when you stay
4.679.776 ₫
5.264.747 ₫ total
20 Aug - 21 Aug
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"Nice place"
Reviewed on 15 Aug 2026
Hyatt Vacation Club at Sunset Harbor, Key West
200 Sunset Lane Key West FL
Fully refundableReserve now, pay when you stay
5.778.869 ₫
7.383.849 ₫ total
31 Aug - 1 Sept
includes taxes & fees
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
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
3.607.088 ₫
5.969.885 ₫ total
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (3,530 reviews)
"The elevator was broken in our building - which I know happens - but it made for lots of stair climbing!"
Reviewed on 17 Aug 2026
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.
Frequently asked questions
How much does a Truman Annex holiday package cost?
Handcraft your Truman Annex package from an affordable . Pick from any combination of hotels, flights and rental cars to build the getaway of your dreams. Don't forget to add on some activities and experiences!
How do I get a cheap travel package to Truman Annex?
One of the easiest ways to save dollars (and time) is to combine your bookings with Expedia. Flights, rental cars, hotels and activities — we've got it all. Pick and choose the combination that best suits you and see your savings grow. We know a package deal is never a one-size-fits-all. That's why Expedia offers over 550 airlines and 1null000null000 hotel options across the world, which lets you customize your Truman Annex adventure.
Where should I stay in Truman Annex?
Most travellers who visit Truman Annex put both Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens on their itineraries. Why not reserve a hotel within walking distance of these great attractions?
What are the top hotels in Truman Annex?
If this will be your first visit to Truman Annex, make a reservation at Serenity On Southard @ The Annex Condo Near Duval And Beach + Last Key Service or A Peace Of Paradise At The Truman Annex In Key West. Both have good amenities and are favourites with many travellers.
How far in advance should I book my Truman Annex holiday?
Search Expedia to compare international fares ASAP. In many cases, you can purchase a seat up to a year prior to departure. If you can't find your preferred carrier, or you have to book last minute, don't stress. Low prices to Truman Annex occasionally appear a few weeks before the date of departure.
What does an Expedia Truman Annex travel package include?
With Expedia, you can select any combination of car rentals, hotels and flights to build your ideal Truman Annex travel package. Once you've made your booking, you can add on the fun things like activities and tours. Remember, the more you bundle, the greater the savings!
What should I know before booking a Truman Annex travel package?
Design deals to suit your budget with an Expedia package. Airfares, hotels, rental cars — we have everything you need to plan your escape. You'll save a tidy sum just by combining your bookings. Whether you're going on a winter adventure or getting some sun on a warm beach, your perfect getaway is just clicks away.
Can I choose my airline with a Truman Annex Expedia holiday package?
Yes, the choice is all yours. Expedia has access to more than 550 partner airlines throughout the world, so you can customize your Truman Annex getaway according to your needs and budget.
If I'm not able to travel, can I cancel my Truman Annex holiday package?
We totally get it — life can throw you the odd curveball. If you've booked a Truman Annex holiday package and need to cancel or change it, we're here to help. We recommend taking a look at our Customer Service Portal first for information. But generally, if you've booked your package in the last 24 hours, you may be able to change your itinerary free of charge. If it's been more than 24 hours, your airline, hotel or car rental company may charge a fee.
Stay near popular Truman Annex attractions
Harry S. Truman Little White House
9.0/10 (995 reviews)
You can spend an afternoon browsing the exhibits at Harry S. Truman Little White House during your travels in Key West. Discover the area's lively festivals or seek out its cycling trails.
Mel Fisher Maritime Museum
9.2/10 (56 reviews)
You can spend time studying the exhibits at Mel Fisher Maritime Museum in Key West. Wander the seaside and beautiful beaches in the area.
Jackson Square
8.8/10 (110 reviews)
You can learn about the history of Key West with a trip to Jackson Square. Stroll along the beautiful beaches or discover the area's beautiful sunsets.
Key West Museum of Art and History
9.0/10 (2 reviews)
You can spend an afternoon studying the exhibits at Key West Museum of Art and History during your travels in Key West. In the area, take in the lively festivals and beautiful sunsets.
Roy John-Karl Gallery
You can spend time browsing the exhibits at Roy John-Karl Gallery in Key West. Stroll along the area's seaside or simply savour its lively bars.
USCGC Ingham Maritime Museum
You can spend an afternoon browsing the exhibits at USCGC Ingham Maritime Museum during your trip to Key West.