Truman Annex Vacation Packages

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Top Holiday Package Deals in Truman Annex

Price found within the past 48 hours. Click for updated prices.
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Key West Historic District
Price was CA $2,563, price is now CA $1,867 per person
CA $1,867
per person
May 24 - May 30
found 22 hours ago
Roundtrip flight included
Montreal (YUL) to Key West (EYW)
9.2/10 Wonderful! (1,003 reviews)
I appreciated the affiliation with Southern Most; being able to use their parking when on the other side of the island. Close proximity to major restaurants and Docks. The Marker has a great breakfast menu and friendly, helpful staff!

Reviewed on Apr 15, 2026

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Price was CA $3,008, price is now CA $1,928 per person
CA $1,928
per person
May 24 - May 30
found 22 hours ago
Roundtrip flight included
Montreal (YUL) to Key West (EYW)
9.4/10 Exceptional! (1,030 reviews)
Very nice room with all amenities

Reviewed on Apr 16, 2026

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Price was CA $2,966, price is now CA $1,922 per person
CA $1,922
per person
May 24 - May 30
found 22 hours ago
Roundtrip flight included
Montreal (YUL) to Key West (EYW)
9.4/10 Exceptional! (1,017 reviews)
Great property. Rooms spacious. Pool beautiful. Only minus is it is a ways from the property to my Key West proper, with Uber and Lyft expensive to get there.

Reviewed on Apr 17, 2026

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was CA $4,512, price is now CA $3,252 per person
CA $3,252
per person
Jul 2 - Jul 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (542 reviews)
Great location! We were very impressed with Chris! He told us where to park and was very welcoming when we arrived. The loft room setup was perfect for us and the Bali Bar did not disappoint! We will be back!!

Reviewed on Apr 5, 2026

Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
Old Town Key West
Price was CA $3,125, price is now CA $2,273 per person
CA $2,273
per person
May 20 - May 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
8.6/10 Excellent! (354 reviews)
Location was great. Near most of Key West Attractions. Parked the car and walked everywhere.

Reviewed on Apr 14, 2026

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
Old Town Key West

Old Town Key West

4 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

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 refundable
The price is CA $462 per night from May 11 to May 12
CA $462
CA $566 total
May 11 - May 12
includes taxes & fees
8.6/10 Excellent! (355 reviews)
Location was great. Near most of Key West Attractions. Parked the car and walked everywhere.

Reviewed on Apr 14, 2026

Hyatt Vacation Club at Sunset Harbor, Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from Apr 19 to Apr 20
CA $233
CA $339 total
Apr 19 - Apr 20
includes taxes & fees
8.2/10 Very Good! (2,101 reviews)
Clean room but cleaning staff was slow to clean, came back to room at 6pm and room still wasn’t cleaned. Pillows are very small but bed was comfortable. Outdoor pool was like a spring break party, with towels, cups and trash everywhere. The outside game area was ripped up on day two and they were ...

Reviewed on Apr 17, 2026

Blue Flamingo Resort Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $402 per night from May 18 to May 19
CA $402
CA $552 total
May 18 - May 19
includes taxes & fees
8.8/10 Excellent! (3,211 reviews)
Great time

Reviewed on Apr 17, 2026

Southernmost Beach Resort and Guesthouses
See all 2,724 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
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Frequently asked questions

How much does a Truman Annex vacation package cost?
Handcraft your Truman Annex package from an affordable CA $1,867. 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

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

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $59
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Aboard the trolley in Key West

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

CA $77
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Kayak the mangrove tidal creeks

Key West Mangrove Kayak Eco Tour

CA $110
per adult
100% of travellers recommend
Key West Mangrove Kayak 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.