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 $1,444, price is now $989 per person
$989
per person
Apr 3 - Apr 6
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 $2,088, price is now $1,376 per person
$1,376
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip 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.
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $2,415, price is now $1,610 per person
$1,610
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
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.
The Perry Hotel & Marina Key West
Price was $2,239, price is now $1,563 per person
$1,563
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
A marina, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference space. 2 poolside bars and 2 bars/lounges are featured at this hotel, along with a 24-hour gym.
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
Old Town Key West
Save 100% on your flight
Price was $3,143, price is now $2,227 per person
$2,227
per person
Apr 8 - Apr 15
found 5 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 and barbecue grills.
Top Truman Annex hotels deals
Hyatt Vacation Club at Sunset Harbor, Key West
200 Sunset Lane Key West FL
$373 nightly
The price is $419 total per night
$419 total
Feb 1 - Feb 2
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
Weatherstation Inn
57 Front St Key West FL
$459 nightly
The price is $516 total per night
$516 total
Feb 1 - Feb 2
Total with 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
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Free Cancellation
$539 nightly
The price is $606 total per night
$606 total
Jan 27 - Jan 28
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
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Free Cancellation
Reserve now, pay when you stay
$443 nightly
The price is $499 total per night
$499 total
Jan 27 - Jan 28
Total with 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
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$312 nightly
The price is $351 total per night
$351 total
Jan 28 - Jan 29
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
$463 nightly
The price is $521 total per night
$521 total
Jan 28 - Jan 29
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
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
