Maui Vacation Deals

From the Lahaina harbor to the shores of Big Beach in Makena, Maui is excitingly diverse. Watch a humpback whale breach the sea. Tee off at a championship golf course. Drive the 53-mile jungly road to Hana or traverse the moonlike volcanic crater of Haleakala. Or just unwind on the beach.  Maui vacation packages offer a variety of choices.

Want more options? See all Maui Vacation Packages.

$200 OFF Hawaii vacations

Book from 08/31/26 to 10/25/26, travel from 08/31/26 to 06/30/27

Haleakala National Park
Haleakala National Park
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Aston at the Whaler on Kaanapali Beach
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$200 OFF Hawaii Vacations

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Kaanapali

Book from 08/31/26 to 10/25/26, travel from 08/31/26 to 06/30/27

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    $200 OFF 5-night vacations

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Requires roundtrip airfare from the continental U.S. and accommodation of 5 nights or longer at a participating hotel or resort. Discount is per booking and taken at time of booking.  Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time. 
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Courtyard by Marriott Maui Kahului Airport
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$200 OFF Hawaii Vacations

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Maui, Kahului, HI

Book from 08/31/26 to 10/25/26, travel from 08/31/26 to 06/30/27

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    $200 OFF 5-night vacations

Book this deal View hotel arrow-right icon
Requires roundtrip airfare from the continental U.S. and accommodation of 5 nights or longer at a participating hotel or resort. Discount is per booking and taken at time of booking.  Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time. 

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We are currently working on enhancements to this part of our website. A new version will be available soon. Don’t worry – switching over will not interrupt your booking.

Welcome to the all-new Pleasant Holidays booking experience !

You can now plan your next vacation with our exciting new booking engine. Some advanced features are still being developed, and selecting these options may require you to return to our traditional booking experience. Don’t worry – switching over will not interrupt your booking.

We've updated your online experience to make sure you can get your dream vacation. Since our makeover is still in progress, you may experience shifts from our traditional booking experience to our new one.

Are you a travel agent ? We are also working on a new digital experience specifically for travel professionals and we can’t wait for you to see it. Until then, please continue to use the traditional experience here: Pleasantagent.com.

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Call 1-800-742-9244
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