Truman Annex Vacations
Book a Hotel + Flight or Car together to unlock savings
Photo by Rick Tuers
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Price found within the past 48 hours. Click for updated prices.
- The Perry Hotel & Marina Key West
Aug 1 - Aug 5The Perry Hotel & Marina Key West + Flight
Stock Island4 nights9.4/10 - Exceptional (1,273 reviews)"Clean, comfortable, friendly, helpful staff. Pool area is convenient and well maintained. Love the shuttle service to and from town"Reviewed May 20, 2026Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • Nonstop EYW - ATL • Nonstop$909$650found 1 day agoper traveler - Hyatt Vacation Club at Windward Pointe, Key West
Aug 1 - Aug 5Hyatt Vacation Club at Windward Pointe, Key West + Flight
Key West4 nights9.4/10 - Exceptional (1,092 reviews)"Excellent room. Clean and walking distance from airport. Great restaurants in walking distance as well. Staff was sufficient but not going the extra mile in terms of getting needs met."Reviewed May 23, 2026Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • Nonstop EYW - ATL • Nonstop - Hyatt Vacation Club at Sunset Harbor, Key West
Aug 1 - Aug 5Hyatt Vacation Club at Sunset Harbor, Key West + Flight
Old Town Key West4 nights8.6/10 - Excellent (371 reviews)"Wished we had paid more for a unit that at least had a window other than to a hallway. Room was clean but not spotless. Found at least 3 long hairs in the bathroom area. Staff at desk was quite abrupt and condescending. At check in AND check out. Gave 4 stars but 5 stars could easily be reached with just a little more attention to detail"Reviewed May 18, 2026Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • Nonstop EYW - ATL • Nonstop - The Key West Hotel
Aug 1 - Aug 5The Key West Hotel + Flight
Key West Historic District4 nights9.2/10 - Wonderful (555 reviews)Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • Nonstop EYW - ATL • Nonstop - Winslow's Bungalows - Key West Historic Inns
Aug 1 - Aug 5Winslow's Bungalows - Key West Historic Inns + Flight
Old Town Key West4 nights9.2/10 - Wonderful (1,292 reviews)Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • Nonstop EYW - ATL • Nonstop$1,153$818found 1 day agoper traveler
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
3 out of top 10 points of interest in this area
4.5/5(229 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.
Truman Annex Hotel Deals
Hyatt Vacation Club at Sunset Harbor, Key West
200 Sunset Lane Key West FL
Fully refundable
$299 nightly
The price is $337 total per night from Jun 17 to Jun 18
$337 total
Jun 17 - Jun 18
Total with taxes and fees
8.6/10 Excellent! (371 reviews)
"Wished we had paid more for a unit that at least had a window other than to a hallway. Room was clean but not spotless. Found at least 3 long hairs in the bathroom area. Staff at desk was quite abrupt and condescending. At check in AND check out. Gave 4 stars but 5 stars could easily be reached with ..."
Reviewed on May 18, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $207 total per night from May 27 to May 28
$207 total
May 27 - May 28
Total with taxes and fees
8.4/10 Very Good! (2,268 reviews)
"Staff was on point , awesome time , would do it again ."
Reviewed on May 23, 2026
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundable
$261 nightly
The price is $294 total per night from Jun 8 to Jun 9
$294 total
Jun 8 - Jun 9
Total with taxes and fees
8.8/10 Excellent! (3,327 reviews)
"The resort was very nice. The pools were great and the room was updated and clean. Great location on Duval Street. Highly recommend."
Reviewed on May 22, 2026
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.
Discover the most popular places to visit in Truman Annex
Harry S. Truman Little White House
4.5/5(842 reviews)
Visit the winter home of President Harry S. Truman to see where some of America’s most important post-war decisions were made.
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.
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 seaside or discover the area's beautiful sunsets.
Things to do
Miami to Key West Day Trip with Activity Options
$39
per adult
84% of travellers recommend
Key West Dolphin & Snorkeling Tour - Small Group
$135
per adult
100% of travellers recommend
Key West Half-Day Fishing Charter
$95
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.