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 Beach House, Key West
Save 100% on your flight
Price was $1,242, price is now $898 per person
$898
per person
Jul 5 - Jul 8
found 1 day ago
Roundtrip 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 WiFi. Self parking, concierge services, and barbecue grills are also on offer.
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,333, price is now $903 per person
$903
per person
Jul 5 - Jul 8
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.
Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
Save 100% on your flight
Price was $1,730, price is now $1,189 per person
$1,189
per person
Jul 17 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
A private beach, a full-service spa, and 2 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the gym and perks like free WiFi.
The Gardens Hotel
Old Town Key West
Save 100% on your flight
Price was $2,112, price is now $1,461 per person
$1,461
per person
Jun 7 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
2 outdoor pools, 2 bars/lounges, and a restaurant are among this bed & breakfast's featured amenities. Business travelers can take advantage of the free WiFi in public areas. Relax with a drink at the poolside bar and enjoy the free cooked-to-order breakfast each morning.
Almond Tree Inn Hotel - Adults Only
Old Town Key West
Save 100% on your flight
Price was $1,868, price is now $1,358 per person
$1,358
per person
Jun 17 - Jun 24
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
Hyatt Vacation Club at Sunset Harbor, Key West
200 Sunset Lane Key West FL
Free Cancellation
$378 nightly
The price is $425 total per night
$425 total
May 11 - May 12
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
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
$211 nightly
The price is $238 total per night
$238 total
May 26 - May 27
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 a playground, 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
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$255 nightly
The price is $287 total per night
$287 total
May 11 - May 12
Total with 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
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
$232 nightly
The price is $261 total per night
$261 total
May 26 - May 27
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
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$371 nightly
The price is $418 total per night
$418 total
May 7 - May 8
Total with taxes and fees
A private beach, a full-service spa, and 2 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the gym and perks like free WiFi.
On private beach
Pool
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$330 nightly
The price is $372 total per night
$372 total
May 19 - May 20
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
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
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.
Frequently asked questions
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