Deals on vacations and trips to Truman Annex
Truman Annex flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,185, price is now $716 per person
$716
per person
May 6 - May 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This hotel features an outdoor pool, a hot tub, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli, concierge services, and barbecue grills are also on offer.
The Key West Hotel
Key West Historic District
Price was $2,861, price is now $1,734 per person
$1,734
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a garden. Luggage storage and concierge services are also provided.
The Marker Key West Harbor Resort
Key West Historic District
Price was $2,694, price is now $1,875 per person
$1,875
per person
May 5 - May 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This smoke-free hotel features 3 outdoor pools, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.
Springtide House by Brightwild Waterfront Pool
Price was $11,617, price is now $8,330 per person
$8,330
per person
May 8 - May 15
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and barbecue grills are also provided.
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
Save 100% on your flight
Price was $2,792, price is now $2,010 per person
$2,010
per person
May 6 - May 13
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this cottage, along with free WiFi in public areas.
Top Truman Annex hotels deals
Hyatt Vacation Club at Sunset Harbor, Key West
200 Sunset Lane Key West FL
$420 nightly
The price is $473 total per night
$473 total
Mar 24 - Mar 25
Total with taxes and fees
An outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free.
Pool
Free WiFi
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Free Cancellation
$501 nightly
The price is $563 total per night
$563 total
Apr 5 - Apr 6
Total with taxes and fees
This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.
Pool
Spa
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
$483 nightly
The price is $544 total per night
$544 total
Mar 25 - Mar 26
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's a 24-hour gym on site, and a 24-hour front desk and dry cleaning are also provided.
Pool
Pet friendly
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$422 nightly
The price is $475 total per night
$475 total
Mar 8 - Mar 9
Total with taxes and fees
This Art Deco hotel features a private beach, a marina, and a restaurant. Enjoy a day at the beach kayaking, or relax with sun loungers. Enjoy the outdoor pool and free perks like continental breakfast and WiFi in public areas.
On private beach
Pool
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
$337 nightly
The price is $379 total per night
$379 total
Mar 10 - Mar 11
Total with taxes and fees
This hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and an arcade/game room, and families will appreciate the picnic area. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and an area shuttle.
Pool
Hot Tub
Hyatt Centric Key West Resort and Spa
601 Front St Key West FL
Free Cancellation
Reserve now, pay when you stay
$418 nightly
The price is $470 total per night
$470 total
Apr 5 - Apr 6
Total with taxes and fees
This smoke-free resort features a full-service spa, a marina, and a restaurant. Enjoy the outdoor pool and perks like free WiFi. Enjoy the 24-hour gym and unwind at the bar/lounge and poolside bar.
Pool
Spa
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.
Popular places to visit
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.
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.
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.
Frequently asked questions
Photos of local treasures
Browse Truman Annex vacation photos for more inspiration
