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
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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 Saint Mary Star of the Sea.

Find hotels in Old Town Key West

Our pick of the best Truman Annex Hotel Deals

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
Fully refundableReserve now, pay when you stay
The price is NZ$518 per night from 17 Nov to 18 Nov
NZ$518
17 Nov - 18 Nov
includes taxes & fees
8.4/10 Very Good! (314 reviews)
Good location

Reviewed on 9 Sept 2025

Hyatt Vacation Club at Sunset Harbor, Key West
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 NZ$392 per night from 14 Dec to 15 Dec
NZ$392
14 Dec - 15 Dec
includes taxes & fees
9.2/10 Wonderful! (981 reviews)
Room spotless. Great quiet location

Reviewed on 30 Oct 2025

Weatherstation Inn
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 NZ$353 per night from 20 Nov to 21 Nov
NZ$353
20 Nov - 21 Nov
includes taxes & fees
8.6/10 Excellent! (1,669 reviews)
Clain for one of the nicest places in Key West

Reviewed on 9 Nov 2025

Beachside Resort & Residences
See all 2,802 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 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.

Discover the most popular places to visit in Truman Annex

Mel Fisher Maritime Museum

Mel Fisher Maritime Museum

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.

Mel Fisher Maritime Museum

Activities

Miami to Key West Day Trip with Activity Options

Miami to Key West Day Trip with Activity Options

NZ$68
per adult
84% of travellers recommend
Miami to Key West Day Trip with Activity Options
Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

NZ$87
per adult
92% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Family navigating the sea on the glass bottom boat in Key West

Key West Sunset Cruise & Glass Bottom Eco Tour

NZ$111
per adult
74% of travellers recommend
Key West Sunset Cruise & Glass Bottom Eco Tour
See all activities in Key West
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.