Truman Annex Vacations from $1,249

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Your Truman Annex Vacation

Take the hassle out of planning your next break with a Truman Annex vacation package. Immerse yourself in the sights and sounds of this enticing neighborhood 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 vacation to Truman Annex, Expedia will help get you there.

The Latest Truman Annex Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
Save 100% on your flight
Price was $1,769, price is now $1,249 per person
$1,249
per person
Mar 4 - Mar 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.2/10 Very Good! (2,000 reviews)
Everything was fantastic

Reviewed on Feb 1, 2026

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
Price was $2,861, price is now $1,641 per person
$1,641
per person
Mar 4 - Mar 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
Good location and service

Reviewed on Feb 1, 2026

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $4,636, price is now $3,100 per person
$3,100
per person
Mar 4 - Mar 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Everything was great. I couldn’t complain about anything if I wanted to. Thanks for a great stay!

Reviewed on Jan 28, 2026

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $4,399, price is now $2,961 per person
$2,961
per person
Mar 4 - Mar 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (2,844 reviews)
Great location with beautiful ocean views. Clean and comfortable rooms and friendly staff. 3 pools to choose from but we spent all of our time at the Shore pool right next to the beach. Can’t wait to visit them again!

Reviewed on Feb 2, 2026

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
New Town
Save 100% on your flight
Price was $2,077, price is now $1,464 per person
$1,464
per person
Mar 4 - Mar 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8/10 Very Good! (1,693 reviews)
Room was clean. Coffee maker in room did not work properly but once we notified them they replaced the one that was in there. Staff was courteous. Elevator did not work very well. Especially if you were not on the first floor. Long waiting time from floors above first floor. A few times had to walk down to first floor to get on and take up to upper floor to load elevator to bring it back down.

Reviewed on Feb 1, 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
Key West Historic District

Old Town Key West

4 out of top 10 points of interest in this area
4.5/5(226 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
$442 nightly
The price is $497 total per night from Feb 3 to Feb 4
$497 total
Feb 3 - Feb 4
Total with taxes and fees
8.4/10 Very Good! (335 reviews)
Highly recommend! Wonderful apartments, clean, well equipped and family friendly.

Reviewed on Jan 29, 2026

Hyatt Vacation Club at Sunset Harbor, Key West
Weatherstation Inn

Weatherstation Inn

2.5 out of 5
57 Front St Key West FL
9.2/10 Wonderful! (999 reviews)
The location was great, and a quiet neighborhood, but near to everything we wanted to see in Key West.

Reviewed on Jan 28, 2026

Get rates
Weatherstation Inn
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundable
$530 nightly
The price is $596 total per night from Feb 3 to Feb 4
$596 total
Feb 3 - Feb 4
Total with taxes and fees
8.6/10 Excellent! (3,047 reviews)
Always our favorite spot. Staff is wonderful. Can’t beat the views and amenities.

Reviewed on Feb 1, 2026

Southernmost Beach Resort and Guesthouses
See all 2,823 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
Kid Friendly Vacations
Kid Friendly Vacations

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
St Maarten and St Martin

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
Jackson Square featuring heritage architecture and an administrative buidling

Jackson Square

You can learn about the history of Key West with a stop at Jackson Square. Stroll along the beautiful beaches or discover the area's beautiful sunsets.

Jackson Square

Things to do

Entertainer in character at the Shipwreck Treasure Museum in Key West

Shipwreck Treasure Museum Tickets

$19
per adult
78% of travellers recommend
Shipwreck Treasure Museum Tickets
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

$45
per adult
88% of travellers recommend
Key West Conch Tour Train
Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included

$79
per adult
98% of travellers recommend
Sunset Sail in Key West with Beverages Included
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.