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.
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,343, price is now $941 per person
$941
per person
Nov 17 - Nov 21
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 Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Save 100% on your flight
Price was $3,423, price is now $2,296 per person
$2,296
per person
Nov 12 - Nov 15
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.
The Gardens Hotel

The Gardens Hotel

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,929, price is now $1,347 per person
$1,347
per person
Nov 21 - Nov 25
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.
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,378, price is now $1,725 per person
$1,725
per person
Nov 6 - Nov 10
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. WiFi in public areas is free. Self parking, a terrace, and a picnic area are also offered.
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,456, price is now $1,782 per person
$1,782
per person
Nov 25 - Dec 1
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. Enjoy the free self-serve breakfast each morning. Self parking, a terrace, and a garden are also offered.

Top Truman Annex hotels deals

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
$228 nightly
The price is $256 total per night
$256 total
Sep 28 - Sep 29
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

Weatherstation Inn

2.5 out of 5
57 Front St Key West FL
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $190 total per night
$190 total
Sep 8 - Sep 9
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
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
$210 nightly
The price is $237 total per night
$237 total
Sep 13 - Sep 14
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
$195 nightly
The price is $219 total per night
$219 total
Sep 7 - Sep 8
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

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$234 nightly
The price is $263 total per night
$263 total
Sep 20 - Sep 21
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like a free airport shuttle. You'll appreciate the hot tub, poolside bar, and concierge services.
Pool
Hot Tub
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
$160 nightly
The price is $180 total per night
$180 total
Sep 7 - Sep 8
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
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See all available properties in Truman Annex
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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?
$941 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.