Truman Annex Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Truman Annex

Price found within the past 48 hours. Click for updated prices.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
per person
Aug 28 - Aug 31
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Key West (EYW)
8.6/10 Excellent! (2,611 reviews)
Beautiful hotel..we stayed at Duval gardens guesthouse on duval street about 5 mins walk from the lobby..bellmen are available for transport..breakfast was nice and pool area was well kept..staff is attentive and made sure we had everything we need

Reviewed on Jul. 26, 2025

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
per person
Aug 28 - Aug 31
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Key West (EYW)
9.2/10 Wonderful! (1,003 reviews)
Property was resort like with a small beach area, pool and tiki bar that served good food and beverages

Reviewed on Jul. 27, 2025

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
per person
Aug 28 - Aug 31
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
Stayed with my husband and 3 kids. The room was very spacious. The balcony was gorgeous overlooking the pool and the ocean. We all agreed for our next family trip we will stay here again. It was very close to the marina where we rented our boat. The island is fairly small so we didn’t feel we missed out by not staying on Duval street, especially with kids. I really appreciated the washer and dryer so we didn’t have to bring home wet bathing suits. The pool area has a volleyball area and outdoor games. Totally worth it to stay here with family.

Reviewed on Jul. 27, 2025

Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Old Town Key West
per person
Sep 8 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
10/10 Exceptional! (1,002 reviews)
Beautiful with excellent customer service. I very much enjoyed being here and didnt want to leave

Reviewed on Jul. 27, 2025

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
per person
Sep 8 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
Had a great time place was awesome. Can’t wait to return

Reviewed on Jul. 26, 2025

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
Default Image

Old Town Key West

3 out of top 10 points of interest in this area
3.5/5(8 area reviews)

Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.

Find hotels in Old Town Key West

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 CA $232 per night from Jul 29 to Jul 30
CA $232
CA $261 total
Jul 29 - Jul 30
includes taxes & fees
9.2/10 Wonderful! (943 reviews)
"The staff went above and beyond for us to have a great vacation and stay!"

Reviewed on Jul. 18, 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 CA $184 per night from Aug 18 to Aug 19
CA $184
CA $276 total
Aug 18 - Aug 19
includes taxes & fees
8.4/10 Very Good! (1,386 reviews)
"I liked everything except the parking fee of $25.00 each night. I loved the towels and bed. I wished there’s a microwave and a bigger refrigerator."

Reviewed on Jul. 27, 2025

Beachside Resort & Residences
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
The price is CA $252 per night from Aug 25 to Aug 26
CA $252
CA $377 total
Aug 25 - Aug 26
includes taxes & fees
8.6/10 Excellent! (2,650 reviews)
"Stay was good but we expected the private beach and it was not clean due to seaweeds so we couldn't use at all. The only reason we booked that hotel due to private beach access which was not available. Otberwise everything was good."

Reviewed on Jul. 27, 2025

Southernmost Beach Resort and Guesthouses
See all 2,774 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Truman Annex vacation package cost?
Handcraft your Truman Annex package from an affordable CA $667. 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 travelers 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 favorites with many travelers.
How far in advance should I book my Truman Annex vacation?
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 vacation 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 vacation package?
We totally get it — life can throw you the odd curveball. If you've booked a Truman Annex vacation 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

Harry S. Truman Little White House showing a house

Harry S. Truman Little White House

Visit the winter home of President Harry S. Truman to see where some of America’s most important post-war decisions were made.

Harry S. Truman Little White House
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

Things to do

Snorkler waving underwater in Key West

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

CA $75
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!

CA $232
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

CA $116
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.