Oahu Vacation Packages | Pleasant Holidays

Hilton Hawaiian Village Waikiki Beach Resort

$200 OFF Hawaii Vacations

Waikiki, Oahu

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. 

OUTRIGGER Waikiki Beach Resort

$200 OFF Hawaii Vacations

Waikiki, Oahu

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. 

'Alohilani Resort Waikiki Beach

$200 OFF Hawaii Vacations

Waikiki, Oahu

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 Twin Fin

$200 OFF Hawaii Vacations

Waikiki, Oahu

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. 

Sheraton Waikiki Beach Resort

$200 OFF Hawaii Vacations

Waikiki, Oahu

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. 

Aulani, Disney Vacation Club Villas

$200 OFF Hawaii Vacations

Ko Olina Resort Area, Oahu

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 Reef Waikiki Beach Resort

$200 OFF Hawaii Vacations

Waikiki, Oahu

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. 

Embassy Suites by Hilton Waikiki Beach Walk

Up to 40% OFF at Embassy Suites by Hilton Waikiki Beach Walk

Waikiki, Oahu

Book from 09/01/26 to 10/31/26, travel from 09/01/26 to 12/31/26

Up to 40% OFF room rates

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Discount varies based on travel dates, length of stay and room category booked. Offer is based on availability and may be discontinued at any time.

Waikiki Beach Marriott Resort & Spa

$200 OFF Hawaii Vacations

Waikiki, Oahu

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. 

Romer House Waikiki

$200 OFF Hawaii Vacations

Waikiki, Oahu

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. 

Waikiki Malia

Up to 20% OFF and Waived Amenity Fee at Waikiki Malia

Waikiki, Oahu

Book from 09/01/26 to 10/31/26, travel from 09/01/26 to 05/31/27

Up to 20% OFF room rates
Amenity fee waived

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Discount varies based on travel dates, length of stay and room category booked. Offer is based on availability and may be discontinued at any time. Minimum two night length of stay required.

OUTRIGGER Waikiki Beachcomber Hotel

$200 OFF Hawaii Vacations

Waikiki, Oahu

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. 