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.
Havana Cabana at Key West
New Town
per person
Sep 22 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and perks like free self parking.
Hyatt Vacation Club at Beach House, Key West
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)
This hotel features an outdoor pool and a hot tub. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A safe deposit box and concierge services are also provided.
Hyatt Vacation Club at Windward Pointe, Key West
per person
Oct 4 - Oct 11
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.
Southernmost Beach Resort and Guesthouses
Old Town Key West
per person
Sep 22 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
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 for business? Take advantage of the 24-hour business center, laundry service, and conference space.
Almond Tree Inn Hotel - Adults Only
Old Town Key West
per person
Sep 22 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and free continental breakfast each morning.
Top Truman Annex hotels deals
Weatherstation Inn
57 Front St, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $190 total per night
$190 total
Aug 3 - Aug 4
Total includes taxes and fees
An outdoor pool, free self parking, and concierge services are featured at this bed & breakfast. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace and free newspapers are also provided.
Pool
Breakfast included
Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$194 nightly
The price is $218 total per night
$218 total
Aug 18 - Aug 19
Total includes taxes and fees
This smoke-free hotel features a private beach, a marina, and 2 restaurants. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and an area shuttle.
On private beach
Pool
Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Free Cancellation
$244 nightly
The price is $275 total per night
$275 total
Aug 25 - Aug 26
Total includes 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 for business? Take advantage of the 24-hour business center, laundry service, and conference space.
Pool
Spa
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$177 nightly
The price is $199 total per night
$199 total
Aug 3 - Aug 4
Total includes taxes and fees
This eco-certified 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 onsite laundry facilities. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and an area shuttle.
Pool
Pet friendly
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$206 nightly
The price is $232 total per night
$232 total
Aug 12 - Aug 13
Total includes taxes and fees
A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. The restaurant provides options for dining, while the bar/lounge and poolside bar are great spots to unwind.
Pool
Pet friendly
Fairfield Inn and Suites by Marriott Key West
2400 N Roosevelt Blvd, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$135 nightly
The price is $151 total per night
$151 total
Aug 24 - Aug 25
Total includes taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free continental breakfast each morning.
Pool
Breakfast included
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
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