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.
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,921, price is now $1,347 per person
$1,347
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Enjoy the hot tub and free continental breakfast each morning. Self parking, a garden, and dry cleaning 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 $3,970, price is now $2,419 per person
$2,419
per person
Dec 31 - Jan 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.
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Key West Historic District
Save 100% on your flight
Price was $2,945, price is now $2,105 per person
$2,105
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This smoke-free hotel features 3 outdoor pools, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,591, price is now $1,871 per person
$1,871
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
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, free WiFi in public areas, and laundry service. 2 poolside bars and 2 bars/lounges are featured at this hotel, along with a gym.
Amelia Home by Avantstay In Historic Old Town w/ Pool

Amelia Home by Avantstay In Historic Old Town w/ Pool

3 out of 5
Old Town Key West
Price was $4,361, price is now $3,171 per person
$3,171
per person
Dec 12 - Dec 19
found 1 day 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

Weatherstation Inn

Weatherstation Inn

2.5 out of 5
57 Front St Key West FL
$199 nightly
The price is $224 total per night
$224 total
Oct 25 - Oct 26
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
Reserve now, pay when you stay
$243 nightly
The price is $274 total per night
$274 total
Oct 28 - Oct 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
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
$275 nightly
The price is $310 total per night
$310 total
Oct 25 - Oct 26
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
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$236 nightly
The price is $265 total per night
$265 total
Oct 30 - Oct 31
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.
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
$166 nightly
The price is $187 total per night
$187 total
Oct 25 - Oct 26
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
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
$202 nightly
The price is $227 total per night
$227 total
Oct 25 - Oct 26
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
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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?
$1,347 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 large, colorful marker labeled 'Southernmost Point' with a view of the ocean and a clear sky in the background.
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.