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 Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was CA $2,137, price is now CA $1,653 per person
CA $1,653
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,282 reviews)
Very Very nice place. We stayed in June the non busy time. Very worth every penny.

Reviewed on Jun 12, 2026

The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was CA $4,404, price is now CA $3,280 per person
CA $3,280
per person
Jul 27 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Key West (EYW)
9.2/10 Wonderful! (559 reviews)
We loved staying here and highly recommended it. Only thing that people might not like is the solo musicians play till 11pm every night. We didn’t mind it since we are not early birds.

Reviewed on Jun 7, 2026

Fitch Lodge - Key West Historic Inns

Fitch Lodge - Key West Historic Inns

3.5 out of 5
Key West Historic District
Price was CA $2,109, price is now CA $1,689 per person
CA $1,689
per person
Jul 27 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Key West (EYW)
8.8/10 Excellent! (624 reviews)
I have stayed in many places in key west, this was by far the cleanest, reliable, friendly and spacious place we have stayed yet.

Reviewed on Apr 30, 2026

Coconut Beach Resort

Coconut Beach Resort

2.5 out of 5
Old Town Key West
Price was CA $2,637, price is now CA $2,155 per person
CA $2,155
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.8/10 Excellent! (194 reviews)
This was a great place to stay! Clean and well-placed on Key West. Pool and patio were great for getting some sun.

Reviewed on May 29, 2026

Amelia Home by Avantstay In Historic Old Town w/ Pool

Amelia Home by Avantstay In Historic Old Town w/ Pool

3 out of 5
Old Town Key West
Price was CA $5,192, price is now CA $4,257 per person
CA $4,257
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
10/10 Exceptional! (3 reviews)
The house was amazing, much more than we expected. We loved the pool area and the landscaping, both were maintained beautifully. The whole place was clean as a whistle!

Reviewed on Oct 7, 2023

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

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

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 refundableReserve now, pay when you stay
The price is CA $345 per night from Jul 20 to Jul 21
CA $345
CA $436 total
Jul 20 - Jul 21
includes taxes & fees
8.6/10 Excellent! (384 reviews)
"Great location, wonderful room, great pool, and great views. Lacking services: no shuttle, no restaurant, you pay resort fees per night but no amenities? We feel like they used the bait and switch on us, great reservation price on room but hit you with nightly fees once you get there. That was our ..."

Reviewed on Jun 16, 2026

Hyatt Vacation Club at Sunset Harbor, Key West
Weatherstation Inn

Weatherstation Inn

2.5 out of 5
57 Front St Key West FL
The price is CA $253 per night from Jun 28 to Jun 29
CA $253
CA $285 total
Jun 28 - Jun 29
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"Thanks."

Reviewed on Jun 16, 2026

Weatherstation Inn
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 $177 per night from Jun 28 to Jun 29
CA $177
CA $279 total
Jun 28 - Jun 29
includes taxes & fees
8.4/10 Very Good! (2,423 reviews)
"Great"

Reviewed on Jun 21, 2026

Blue Flamingo Resort Key West
See all 2,693 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
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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 $1,653. 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 $62
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 $36
per child
88% 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

CA $76
per adult
86% of travellers recommend
Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch
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.