Maui Vacation Packages | Pleasant Holidays

Wailea Beach Resort - Marriott, Maui

$200 OFF Hawaii Vacations

Wailea, Maui

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

$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. 

The Westin Maui Resort & Spa, Kaanapali

$200 OFF Hawaii Vacations

Kaanapali

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

$200 OFF 5-night vacations

Book this deal View hotel

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. 

Fairmont Kea Lani, Maui

$200 OFF Hawaii Vacations

Wailea, Maui

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

$200 OFF 5-night vacations

Book this deal View hotel

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. 

Grand Wailea, A Waldorf Astoria Resort

$200 OFF Hawaii Vacations

Wailea, Maui

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

$200 OFF 5-night vacations

Book this deal View hotel

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. 

Aston Kaanapali Shores

$200 OFF Hawaii Vacations

Kaanapali

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

$200 OFF 5-night vacations

Book this deal View hotel

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. 

Andaz Maui at Wailea Resort - a concept by Hyatt

$200 OFF Hawaii Vacations

Wailea, Maui

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

$200 OFF 5-night vacations

Book this deal View hotel

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. 

OUTRIGGER Ka'anapali Beach Resort

$200 OFF Hawaii Vacations

Kaanapali

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

$200 OFF 5-night vacations

Book this deal View hotel

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. 

Royal Lahaina Resort & Bungalows

$200 OFF Hawaii Vacations

Kaanapali

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

$200 OFF 5-night vacations

Book this deal View hotel

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. 

The Ritz-Carlton Maui, Kapalua

$200 OFF Hawaii Vacations

Kapalua, Maui

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

$200 OFF 5-night vacations

Book this deal View hotel

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. 

Maui Kaanapali Villas

$200 OFF Hawaii Vacations

Kaanapali

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

$200 OFF 5-night vacations

Book this deal View hotel

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. 

Castle Kamaole Sands

$200 OFF Hawaii Vacations

Kihei, Maui

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

$200 OFF 5-night vacations

Book this deal View hotel

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. 

Aston at Papakea Resort

$200 OFF Hawaii Vacations

Kaanapali

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

$200 OFF 5-night vacations

Book this deal View hotel

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. 

Maui Deals

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We've found hotels for you based on your selection.

Wailea Beach Resort - Marriott, Maui

The Westin Maui Resort & Spa, Kaanapali

Fairmont Kea Lani, Maui

Grand Wailea, A Waldorf Astoria Resort

Aston Kaanapali Shores

Andaz Maui at Wailea Resort - a concept by Hyatt

OUTRIGGER Ka'anapali Beach Resort

Royal Lahaina Resort & Bungalows

The Ritz-Carlton Maui, Kapalua

Maui Kaanapali Villas

Castle Kamaole Sands

Aston at Papakea Resort

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Maui Deals

Filters

Choose Your Maui Vacation Deal

We've found hotels for you based on your selection.

Wailea Beach Resort - Marriott, Maui

The Westin Maui Resort & Spa, Kaanapali

Fairmont Kea Lani, Maui

Grand Wailea, A Waldorf Astoria Resort

Aston Kaanapali Shores

Andaz Maui at Wailea Resort - a concept by Hyatt

OUTRIGGER Ka'anapali Beach Resort

Royal Lahaina Resort & Bungalows

The Ritz-Carlton Maui, Kapalua

Maui Kaanapali Villas

Castle Kamaole Sands

Aston at Papakea Resort

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