Truman Annex Vacations from $806

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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.
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,453, price is now $806 per person
$806
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,005 reviews)
Everyone and everything was great, such a great location to enjoy the whole island!

Reviewed on Sep 28, 2025

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Key West Historic District
Price was $1,626, price is now $838 per person
$838
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (819 reviews)
Everything was amazing. we arrived early and in a rain storm my two kids and I were soaked head to toe and the water even entered our luggage. they let us check in early got us en upgrade to. amazing staff and perfect spot close to all in Key West

Reviewed on Sep 25, 2025

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,471, price is now $810 per person
$810
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (791 reviews)
Second mother / daughter trip to Key West - first time staying at Lighthouse Hotel. We loved it! The hotel is charming and the location is perfect. The staff was super friendly and answered all of our questions. Pool area and bar is great and we enjoyed a nice breakfast every morning before venturing out for the day. We rented bikes to get around and this location was ideal - easy ride to everywhere we wanted to go. We had a great stay and will definitely book this hotel again!

Reviewed on Sep 22, 2025

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $2,417, price is now $1,454 per person
$1,454
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (496 reviews)
Excellent location right in the heart of town super friendly staff and very nice property

Reviewed on Aug 3, 2025

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,291, price is now $841 per person
$841
per person
Nov 30 - Dec 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
9.4/10 Exceptional! (1,025 reviews)
The 2 bedroom villa was great. It was spacious and comfortable. The master bathroom was a dream! I also enjoyed the screened in balcony with a view of the ocean and pool. I highly recommend this place!

Reviewed on Sep 30, 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
Key West Historic District

Old Town Key West

3 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

Weatherstation Inn

Weatherstation Inn

2.5 out of 5
57 Front St, Key West, FL
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $186 total per night from Oct 27 to Oct 28
$186 total
Oct 27 - Oct 28
Total with taxes and fees
9.2/10 Wonderful! (957 reviews)
Beautiful Key West location
"Amazing stay at Weatherstation Inn. Perfect location in beautiful Truman Annex neighborhood. Short walk to historic Key West Duvall st, Mallory Square, and harbor."

Reviewed on Sep 22, 2025

Weatherstation Inn
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
8.4/10 Very Good! (314 reviews)
"Good location"

Reviewed on Sep 9, 2025

Get rates
Hyatt Vacation Club at Sunset Harbor, Key West
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
$235 nightly
The price is $264 total per night from Oct 14 to Oct 15
$264 total
Oct 14 - Oct 15
Total with taxes and fees
8.6/10 Excellent! (1,790 reviews)
"We went during off peak season and it was amazing and quiet, relaxing."

Reviewed on Sep 23, 2025

Margaritaville Beach House Key West
See all 2,795 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

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

$50
per adult
92% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Commotion on the Ocean Sunset Sail

Key West Sunset Sail with Live Music, Drinks and Appetizers!

$80
per adult
92% of travellers recommend
Key West Sunset Sail with Live Music, Drinks and Appetizers!
12 hours Day at Key West With Boat Tour and Snorkeling

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

$27
per adult
80% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
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.