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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Wailea Beach Resort - Marriott, Maui
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$200 OFF Hawaii Vacations

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Wailea, Maui

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

Property View
Property View
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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The Westin Maui Resort & Spa, Kaanapali
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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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Fairmont Kea Lani, Maui
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$200 OFF Hawaii Vacations

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Wailea, Maui

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

Main
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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Grand Wailea, A Waldorf Astoria Resort
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$200 OFF Hawaii Vacations

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Wailea, Maui

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

Property View
Property View
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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Aston Kaanapali Shores
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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

Aerial View
Aerial View
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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Andaz Maui at Wailea Resort - a concept by Hyatt
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$200 OFF Hawaii Vacations

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Wailea, Maui

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

Property
Property
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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OUTRIGGER Ka'anapali Beach Resort
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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

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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Royal Lahaina Resort & Bungalows
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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

Main
Main
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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The Ritz-Carlton Maui, Kapalua
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$200 OFF Hawaii Vacations

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Kapalua, Maui

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

Property
Property
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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Maui Kaanapali Villas
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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

  • check-small icon

    $200 OFF 5-night vacations

Property
Property
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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Castle Kamaole Sands
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$200 OFF Hawaii Vacations

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Kihei, Maui

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

Property View
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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Aston at Papakea Resort
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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

  • check-small icon

    $200 OFF 5-night vacations

Property
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.

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