Truman Annex Holidays

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Your Truman Annex Holiday

Take the hassle out of planning your next break with a Truman Annex holiday package. Immerse yourself in the sights and sounds of this enticing neighbourhood and enjoy what it has to offer. Kick off your trip to Truman Annex by visiting nearby attractions such as Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Stop dreaming and start doing. When it's time to book your dream holiday to Truman Annex, Expedia will help get you there.

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

3 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

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 AU$296 per night from 8 Sept to 9 Sept
AU$296
8 Sept - 9 Sept
includes taxes & fees
9.2/10 Wonderful! (947 reviews)
nice property
"nice property with friendly staff in a beautiful, off-the-beaten-path location. will definitely stay again."

Reviewed on 7 Aug. 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 AU$297 per night from 25 Aug to 26 Aug
AU$297
25 Aug - 26 Aug
includes taxes & fees
8.4/10 Very Good! (1,471 reviews)
"I decided to go with this property despite some negative reviews and I am so glad i did. The entire stay was perfect. Staff was so nice and helpful. Special shout out to Ro for making sure we were taken care of. Definitely book again!"

Reviewed on 20 Aug. 2025

Beachside Resort & Residences
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is AU$221 per night from 1 Sept to 2 Sept
AU$221
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (1,069 reviews)
"Most excellent facility with very accommodating staff."

Reviewed on 18 Aug. 2025

Hilton Garden Inn Key West / The Keys Collection
See all 2,759 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.
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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.

Activities

Snorkler waving underwater in Key West

Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch

AU$84
per adult
84% of travellers recommend
Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch
Key West Jet Ski Tour – High-Speed Adventure Around the Island

Ultimate 90 minute Sea Doo Jet Ski Tour of Key West -Additional Rider Free!

AU$260
per traveller
94% of travellers recommend
Ultimate 90 minute Sea Doo Jet Ski Tour of Key West -Additional Rider Free!
Crew member guiding mother and daughter parasailing in Key West

Parasailing in Key West – Soar Above the Island Paradise

AU$130
per traveller
86% of travellers recommend
Parasailing in Key West – Soar Above the Island Paradise
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.