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 $1,522, price is now $977 per person
$977
per person
Jul 14 - Jul 18
found 1 day ago
Roundtrip non-stop 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 House - Adult Exclusive
Old Town Key West
Price was $2,174, price is now $1,243 per person
$1,243
per person
Jun 1 - Jun 6
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. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Self parking, a terrace, and a picnic area are also offered.
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $2,292, price is now $1,407 per person
$1,407
per person
Jun 27 - Jul 2
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.
Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,537, price is now $981 per person
$981
per person
Jul 14 - Jul 18
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 WiFi. Self parking, concierge services, and barbecue grills are also on offer.
The Gardens Hotel
Old Town Key West
Save 100% on your flight
Price was $1,580, price is now $1,080 per person
$1,080
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip 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.
Top Truman Annex hotels deals
Hyatt Vacation Club at Sunset Harbor, Key West
200 Sunset Lane Key West FL
$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.
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
$227 nightly
The price is $256 total per night
$256 total
May 20 - May 21
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.
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$260 nightly
The price is $293 total per night
$293 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
$283 nightly
The price is $319 total per night
$319 total
May 18 - May 19
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.
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$220 nightly
The price is $248 total per night
$248 total
Apr 22 - Apr 23
Total with taxes and fees
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.
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
$373 nightly
The price is $419 total per night
$419 total
May 3 - May 4
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
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.
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