Truman Annex Vacations from $660

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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.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (1,668 reviews)
My fiancé and I were married on Smathers Beach and we chose Oceans Edge Resort for our week in the keys. Absolutely loved it!

Reviewed on Jul 28, 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
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,003 reviews)
Property was resort like with a small beach area, pool and tiki bar that served good food and beverages

Reviewed on Jul 27, 2025

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Save 100% on your flight
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
Stayed with my husband and 3 kids. The room was very spacious. The balcony was gorgeous overlooking the pool and the ocean. We all agreed for our next family trip we will stay here again. It was very close to the marina where we rented our boat. The island is fairly small so we didn’t feel we missed out by not staying on Duval street, especially with kids. I really appreciated the washer and dryer so we didn’t have to bring home wet bathing suits. The pool area has a volleyball area and outdoor games. Totally worth it to stay here with family.

Reviewed on Jul 27, 2025

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Save 100% on your flight
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (2,611 reviews)
Beautiful hotel..we stayed at Duval gardens guesthouse on duval street about 5 mins walk from the lobby..bellmen are available for transport..breakfast was nice and pool area was well kept..staff is attentive and made sure we had everything we need

Reviewed on Jul 26, 2025

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,019 reviews)
We loved our stay at the Perry resort, they should rename it the Triple J Resort. Jayme, Johny and Jeremy absolutely made our stay!

Reviewed on Jul 27, 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
$169 nightly
The price is $190 total per night from Jul 29 to Jul 30
$190 total
Jul 29 - Jul 30
Total includes taxes and fees
9.2/10 Wonderful! (943 reviews)
"The staff went above and beyond for us to have a great vacation and stay!"

Reviewed on Jul 18, 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
$194 nightly
The price is $218 total per night from Aug 19 to Aug 20
$218 total
Aug 19 - Aug 20
Total includes taxes and fees
8.4/10 Very Good! (1,386 reviews)
"I liked everything except the parking fee of $25.00 each night. I loved the towels and bed. I wished there’s a microwave and a bigger refrigerator."

Reviewed on Jul 27, 2025

Beachside Resort & Residences
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
$244 nightly
The price is $275 total per night from Aug 25 to Aug 26
$275 total
Aug 25 - Aug 26
Total includes taxes and fees
8.6/10 Excellent! (2,650 reviews)
"Stay was good but we expected the private beach and it was not clean due to seaweeds so we couldn't use at all. The only reason we booked that hotel due to private beach access which was not available. Otberwise everything was good."

Reviewed on Jul 27, 2025

Southernmost Beach Resort and Guesthouses
See all 2,761 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
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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

4.5/5(834 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
St Maarten and St Martin

Mel Fisher Maritime Museum

4.5/5(47 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
Jackson Square featuring heritage architecture and an administrative buidling

Jackson Square

4.5/5(81 reviews)

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

Crew member guiding mother and daughter parasailing in Key West

Parasailing in Key West – Soar Above the Island Paradise

$54
per traveler
86% of travellers recommend
Parasailing in Key West – Soar Above the Island Paradise
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres

$134
per adult
100% of travellers recommend
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
Entering the Harry S Trueman Little White House in Key West

Harry S. Truman Little White House Tour

$26
per adult
98% of travellers recommend
Harry S. Truman Little White House 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.