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.
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Price was $2,055, price is now $1,397 per person
$1,397
per person
May 25 - May 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This hotel features an outdoor pool and a poolside bar. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.
Southernmost House - Adult Exclusive
Old Town Key West
Price was $3,100, price is now $1,708 per person
$1,708
per person
May 25 - May 31
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
Price was $3,024, price is now $2,048 per person
$2,048
per person
May 25 - May 31
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.
Southernmost Beach Resort and Guesthouses
Old Town Key West
Price was $1,999, price is now $1,432 per person
$1,432
per person
May 25 - May 31
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 on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
Save 100% on your flight
Price was $3,526, price is now $2,532 per person
$2,532
per person
Jul 9 - Jul 16
found 14 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
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.
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 21 - May 22
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.
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
$265 nightly
The price is $298 total per night
$298 total
May 20 - May 21
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
$278 nightly
The price is $312 total per night
$312 total
Apr 27 - Apr 28
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
Free Cancellation
Reserve now, pay when you stay
$372 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.
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 seaside or discover the area's beautiful sunsets.
Frequently asked questions
Photos of local treasures
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