Truman Annex Holidays from AU$4,403

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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.

Top Holiday Package Deals in Truman Annex

Price found within the past 48 hours. Click for updated prices.
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
New Town
Price was AU$5,663, price is now AU$4,403 per person
AU$4,403
per person
9 Jan - 15 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Key West (EYW)
8/10 Very Good! (1,693 reviews)
Love this place rooms are wonderful pool view is great. Employees all speak English and are so nice and helpful. Especially Flora

Reviewed on 5 Dec 2025

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was AU$6,020, price is now AU$5,061 per person
AU$5,061
per person
9 Jan - 15 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
The staff was courteous. The room was beautiful n spotless. But the refrigerators weren't working correctly n my food that I brought was spoiled. Ms. Gwendolyn, provided excellent service and Ms. Sophia, provided discount for my stayed. Also the showers needs to be repaired, it leaked when taking showers. Water was all over the floors, so we put towels on the floor to soak up the water. *At the restaurant Alex was an awesome server, highly recommend him*.

Reviewed on 3 Dec 2025

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was AU$5,803, price is now AU$4,918 per person
AU$4,918
per person
9 Jan - 15 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Key West (EYW)
9.4/10 Exceptional! (1,151 reviews)
Property was clean and the room we stayed in had direct pool access so a morning swim was easy. Be advised there is some noise from the local airport and navy base but this didn’t bother me.

Reviewed on 5 Dec 2025

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Price was AU$6,353, price is now AU$5,424 per person
AU$5,424
per person
9 Jan - 15 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Key West (EYW)
8.6/10 Excellent! (2,844 reviews)
Resort was fantastic and grounds were kept beautiful and clean. Staff was friendly and helpful. We ate at onsite restaurant and food was delicious.

Reviewed on 5 Dec 2025

Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Key West Historic District
Price was AU$7,417, price is now AU$6,356 per person
AU$6,356
per person
9 Jan - 15 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Key West (EYW)
9/10 Wonderful! (1,006 reviews)
Lovely hotel, great room and ideal location.

Reviewed on 30 Nov 2025

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 Ernest Hemingway Home and Museum.

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
The price is AU$463 per night from 8 Dec to 9 Dec
AU$463
8 Dec - 9 Dec
includes taxes & fees
8.4/10 Very Good! (317 reviews)
Spacious suite fully furnished and equipped. Spectacular view and great location

Reviewed on 19 Nov 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 AU$330 per night from 18 Dec to 19 Dec
AU$330
18 Dec - 19 Dec
includes taxes & fees
9.2/10 Wonderful! (987 reviews)
Very nice Inn, very walkable.

Reviewed on 28 Nov 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$348 per night from 15 Dec to 16 Dec
AU$348
15 Dec - 16 Dec
includes taxes & fees
8.6/10 Excellent! (1,734 reviews)
Staff very courteous! We arrived very early- hoping we could at least chk our bags before going to lunch ( 2 couples- booking two rooms). Our friends' room was already available .We were told ours would be ready soon. We had a lovely, long, leisurely lunch at Chicken Walk. Our room still wasnt ready ...

Reviewed on 3 Dec 2025

Beachside Resort & Residences
See all 2,814 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 AU$4,403. 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

Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

AU$89
per adult
86% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Snorkler waving underwater in Key West

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

AU$85
per adult
86% of travellers recommend
Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch
See Key West's most famous landmarks from the water

Key West Sushi Sunset Cruise with Complementary Drinks

AU$116
per adult
100% of travellers recommend
Key West Sushi Sunset Cruise with Complementary Drinks
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.