Truman Annex Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Rick Tuers

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
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Old Town Key West

4 out of top 10 points of interest in this area
5/5(6 area reviews)

While visiting Old Town Key West, you might make a stop by sights like Duval Street and Ernest Hemingway Home and Museum.

Find hotels in Old Town Key West

Top hotels in Truman Annex

Weatherstation Inn

Weatherstation Inn

2.5 out of 5
57 Front St Key West FL
Fully refundableReserve now, pay when you stay
The price is 5.762.328 ₫ per night from 18 Dec to 19 Dec
5.762.328 ₫
6.482.619 ₫ total
18 Dec - 19 Dec
includes taxes & fees
9.2/10 Wonderful! (990 reviews)
Breakfast was good but even though we were few guests, there was not a table to have the breakfast. The location was the best because of the tranquility and the beauty of the neighborhood, and the closeness to the most representative historic attractions of the Key.

Reviewed on 7 Dec 2025

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 7.080.559 ₫ per night from 18 Dec to 19 Dec
7.080.559 ₫
8.854.251 ₫ total
18 Dec - 19 Dec
includes taxes & fees
8.4/10 Very Good! (320 reviews)
Very clean, great location, nice staff, beautiful pool area.

Reviewed on 13 Dec 2025

Hyatt Vacation Club at Sunset Harbor, Key West
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is 4.404.629 ₫ per night from 17 Dec to 18 Dec
4.404.629 ₫
6.287.253 ₫ total
17 Dec - 18 Dec
includes taxes & fees
8.6/10 Excellent! (1,780 reviews)
It was overall great but one night at 2 am the fire alarm went off for Like 25mins and no body give reasons not even a single staff member was there to provide guidance or shutdown the alarms

Reviewed on 14 Dec 2025

Beachside Resort & Residences
See all 2,827 properties in Truman Annex
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.

Popular places to visit

Harry S. Truman Little White House featuring a house

Harry S. Truman Little White House

4.5/5(12 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.

Harry S. Truman Little White House
Jackson Square which includes heritage architecture and an administrative building

Jackson Square

You can learn about the history of Key West with a trip to Jackson Square. Stroll along the seaside or discover the area's beautiful sunsets.

Jackson Square
Key West Museum of Art and History

Key West Museum of Art and History

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.

Key West Museum of Art and History