Truman Annex Vacation Packages 2025/2026 from $1,007

Truman Annex flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Bishop Hotel Key West

Old Town Key West

Save 100% on your flight

$1,007

per person

Nov 12 - Nov 19

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This guesthouse's 2 outdoor pools and hot tub are among the featured amenities. Unwind with a drink at the poolside bar and enjoy perks like free continental breakfast and free WiFi. There's luggage storage and multilingual staff can provide around-the-clock assistance.

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$1,151

per person

Nov 2 - Nov 9

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.

Lighthouse Hotel - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$1,351

per person

Nov 2 - Nov 9

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.

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$1,436

per person

Nov 2 - Nov 9

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. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Self parking, a garden, and luggage storage are also offered.

The Perry Hotel & Marina Key West

Save 100% on your flight

$1,827

per person

Nov 2 - Nov 9

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.

Top Truman Annex hotels deals

Weatherstation Inn

57 Front St, Key West, FL

$169 nightly

$190 total

Aug 27 - Aug 28

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

Hyatt Vacation Club at Sunset Harbor, Key West

200 Sunset Lane, Key West, FL

Free Cancellation

$281 nightly

$317 total

Aug 27 - Aug 28

Total with taxes and fees

An outdoor pool, self parking, and concierge services are featured at this apartment. WiFi in public areas is free.

Pool

Free WiFi

Beachside Resort & Residences

3841 N Roosevelt Blvd, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$184 nightly

$207 total

Aug 27 - Aug 28

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

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$219 nightly

$247 total

Sep 2 - Sep 3

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

Hilton Garden Inn Key West / The Keys Collection

3850 N Roosevelt Blvd, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$126 nightly

$142 total

Sep 1 - Sep 2

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Unwind with a drink at the bar/lounge and enjoy perks like a free area shuttle.

Pool

Pet friendly

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$160 nightly

$180 total

Sep 24 - Sep 25

Total with taxes and fees

This eco-certified 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 onsite laundry facilities. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and an area 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.

Popular places to visit

Harry S. Truman Little White House

4.5/5(834 reviews)

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

4.5/5(47 reviews)

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

4.5/5(81 reviews)

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

How much are vacation packages to Truman Annex?

$1,007 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.