Truman Annex Holidays
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Our guide on 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.
Our pick of the best Truman Annex Hotel Deals
Weatherstation Inn
57 Front St Key West FL
Fully refundableReserve now, pay when you stay
NZ$342
17 Aug - 18 Aug
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"We loved the location of this property. it was close to Duval Street and the property was beautiful. our room gorgeous. The staff was friendly. We used their pool every day. It was very quiet and was located on a beautiful street. The only issues we had was that the door to the room stuck a bit and ..."
Reviewed on 13 Aug 2026
Hyatt Vacation Club at Sunset Harbor, Key West
200 Sunset Lane Key West FL
Fully refundableReserve now, pay when you stay
NZ$479
31 Aug - 1 Sept
includes taxes & fees
8.6/10 Excellent! (410 reviews)
"The location was great, the rooms are beginning to show some age and the staff is good , but not outstanding."
Reviewed on 12 Aug 2026
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
NZ$388
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (3,522 reviews)
"Older resort but still nice, clean. The sargassum was in full force and the smell was very unpleasant but not the resorts fault. Amenities provided were nice. Pool area bars close way to early, adult only pool doesn’t have drinks available without walking. To neighboring pool. Close to sightseeing ..."
Reviewed on 14 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 1 000 000 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)
Discover the historic significance of this presidential home, where Harry S. Truman and his successors made decisions that shaped the world.
Mel Fisher Maritime Museum
9.2/10 (56 reviews)
Key West’s definitive maritime museum is an important attraction for anyone wanting to learn about early life in the Keys. Hear stories of slavery, pirates and fishermen.
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.
Activities
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
NZ$78
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
NZ$137
per adult
94% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
NZ$96
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.