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.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was CA $2,318, price is now CA $1,571 per person
CA $1,571
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9/10 Wonderful! (1,722 reviews)
Nice rooms. Pool water needs attention due to some algae growth on bottom.

Reviewed on Aug. 21, 2025

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was CA $3,299, price is now CA $2,241 per person
CA $2,241
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.4/10 Exceptional! (1,068 reviews)
easy access to fishing, shuttle to key west, great rooms

Reviewed on Aug. 20, 2025

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Old Town Key West
Price was CA $2,903, price is now CA $1,988 per person
CA $1,988
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.4/10 Exceptional! (366 reviews)
everything was easy and staff was very helpful!

Reviewed on Aug. 18, 2025

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Price was CA $2,789, price is now CA $1,972 per person
CA $1,972
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
8.6/10 Excellent! (2,697 reviews)
Great stay awesome staff we will definitely stay here again.

Reviewed on Aug. 20, 2025

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
Price was CA $2,359, price is now CA $1,675 per person
CA $1,675
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9/10 Wonderful! (775 reviews)
The property is cute with its own unique vibe. Our room did smell a bit musty, but it’s damp south Florida…so I took that with a grain of salt. There was some mold in our bathroom grout also, but I wasn’t in the mood to complain about something so petty. One thing I will rave about was Jefferson, he was working at the pool bar and not only was he a joy to talk to, he made a great drink!

Reviewed on Aug. 19, 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 $234 per night from Aug 24 to Aug 25
CA $234
CA $264 total
Aug 24 - Aug 25
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 Aug. 7, 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 $174 per night from Aug 25 to Aug 26
CA $174
CA $266 total
Aug 25 - Aug 26
includes taxes & fees
8.4/10 Very Good! (1,468 reviews)
gorgeous view
"It was so nice—we ended up with a gorgeous view."

Reviewed on Aug. 18, 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 CA $140 per night from Sep 1 to Sep 2
CA $140
CA $197 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,069 reviews)
"Most excellent facility with very accommodating staff."

Reviewed on Aug. 18, 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.
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 $1,571. 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

4/5(28 reviews)

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

3.5/5(3 reviews)

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 $76
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 $234
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 $117
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.