Deals on vacations and trips to Truman Annex

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Truman Annex flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,324, price is now $828 per person
$828
per person
Oct 17 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This smoke-free hotel features 3 outdoor pools, a bar/lounge, and a poolside bar. WiFi in public areas is free. Self parking, a garden, and luggage storage are also offered.
The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Save 100% on your flight
Price was $5,230, price is now $3,042 per person
$3,042
per person
Oct 23 - Oct 26
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.
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,466, price is now $1,471 per person
$1,471
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip 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.
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $1,509, price is now $974 per person
$974
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this hotel, along with free WiFi in public areas and luggage storage. Enjoy the free buffet breakfast each morning. Concierge services are provided for your convenience.
Kona Kai Oasis

Kona Kai Oasis

3 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,496, price is now $997 per person
$997
per person
Oct 17 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
An outdoor pool, free self parking, and concierge services are featured at this guesthouse. WiFi in public areas is free. A garden, a picnic area, and luggage storage are also on offer.

Top Truman Annex hotels deals

Weatherstation Inn

Weatherstation Inn

2.5 out of 5
57 Front St Key West FL
Free Cancellation
Reserve now, pay when you stay
$179 nightly
The price is $201 total per night
$201 total
Aug 20 - Aug 21
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 self-serve breakfast and WiFi in public areas. A garden and a library are also provided.
Pool
Breakfast included
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
200 Sunset Lane Key West FL
Free Cancellation
$276 nightly
The price is $310 total per night
$310 total
Aug 31 - Sep 1
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
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$203 nightly
The price is $228 total per night
$228 total
Sep 1 - Sep 2
Total with taxes and fees
A full-service spa, 3 outdoor pools, and a restaurant are all featured at this hotel. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services. 2 poolside bars and 2 bars/lounges are featured at this hotel, along with a gym.
Pool
Spa
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$184 nightly
The price is $207 total per night
$207 total
Aug 17 - Aug 18
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
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$136 nightly
The price is $153 total per night
$153 total
Aug 17 - Aug 18
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
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

4 out of 5
2801 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$191 nightly
The price is $215 total per night
$215 total
Aug 30 - Aug 31
Total with taxes and fees
This smoke-free hotel features 4 outdoor pools, a gym, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Unwind with a drink at the bar/lounge and enjoy perks like a free beach shuttle.
Pool
Pet friendly
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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.

Stay near popular Truman Annex attractions

A historical marker for The Little White House, built in 1890, used by American Navy officers, and listed on the National Register of Historic Places in 1974.

Harry S. Truman Little White House

9.0/10 (995 reviews)
Visit the winter home of President Harry S. Truman to see where some of America’s most important post-war decisions were made.
See properties

Frequently asked questions

How much are vacation packages to Truman Annex?
$828 is all you need to spend for an exciting break in Truman Annex. Bundle your hotel and flights into a Travelocity vacation package and see how much the savings start to add up. With such good prices, it's never been more tempting to travel.
Where can I get the best vacation package deals for Truman Annex?
Travelocity is here to help you snap up an unbeatable Truman Annex package deal. With as many as 400 partner airlines and 1,000,000 properties across the world, you're bound to find the perfect mix.
Why should I book my Truman Annex vacation package with Travelocity?
Because life is one amazing journey, and we've got everything you need to get you on your way. With our top-quality service and Price Match Guarantee, you can book with confidence. And you can rest easy on the road knowing we're always available to chat via our round-the-clock support.
Will I save money on my Truman Annex car rental if I bundle it with my hotel or flight?
Combining your bookings into a Truman Annex vacation package will certainly save you money. You can combine a flight and car; a flight, hotel and car; or a hotel and car. You won't find a better way to explore the greater Truman Annex region than with your own ride. You can also add experiences and activities to your Travelocity package.

Photos of local treasures

Browse Truman Annex vacation photos for more inspiration

A white building with American flags and a sign for 'Harry's Truman Overseas Hotel'.
A series of tall, slender poles against a clear blue sky.
A large red brick building with arched windows and a tiled roof, surrounded by palm trees.
A sunset over a calm sea with a pier extending into the water.
A tree-lined sidewalk with a white picket fence and lush greenery.