Oahu Vacation Deals

Oahu, "The Gathering Place," is home to Honolulu, Hawaii's largest city. Iconic Waikiki dazzles with its classic beaches, exciting nightlife and world-class cuisine. The North Shore is a surfer's paradise, home to the Banzai pipeline and scenic rainforests, offering a laid-back island style visitors are sure to enjoy. To the West, Pearl Harbor is rich in history with its WWII memorials and massive ships. Throughout the island a fusion of asian, polynesian and western culture give Oahu a flavor all its own. Enjoy the best deals to Oahu with our Hawaii vacation packages.

Want more options? See all Oahu Vacation Packages.

$200 OFF Hawaii vacations

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

Diamond Head Crater
Diamond Head Crater
Filters
All Vacation Deals
Hawaii
Oahu

Choose Your Oahu Vacation Deals

We've found hotels for you based on your selection.
Book now
hotel icon
airplane icon
Hilton Hawaiian Village Waikiki Beach Resort
star-full icon
star-full icon
star-full icon
star-full icon
star-half icon

$200 OFF Hawaii Vacations

map-full icon

Waikiki, Oahu

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

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. 
hotel icon
airplane icon
OUTRIGGER Waikiki Beach Resort
star-full icon
star-full icon
star-full icon
star-full icon
star-half icon

$200 OFF Hawaii Vacations

map-full icon

Waikiki, Oahu

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

Book this deal View hotel arrow-right icon
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. 
hotel icon
airplane icon
'Alohilani Resort Waikiki Beach
star-full icon
star-full icon
star-full icon
star-full icon
star-half icon

$200 OFF Hawaii Vacations

map-full icon

Waikiki, Oahu

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

Book this deal View hotel arrow-right icon
Pool
Pool
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. 
hotel icon
airplane icon
The Twin Fin
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

$200 OFF Hawaii Vacations

map-full icon

Waikiki, Oahu

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

Book this deal View hotel arrow-right icon
Exterior View - hotel and beach
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. 
hotel icon
airplane icon
Sheraton Waikiki Beach Resort
star-full icon
star-full icon
star-full icon
star-full icon
star-half icon

$200 OFF Hawaii Vacations

map-full icon

Waikiki, Oahu

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

Book this deal View hotel arrow-right icon
Exterior
Exterior
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. 
hotel icon
airplane icon
Aulani, Disney Vacation Club Villas
star-full icon
star-full icon
star-full icon
star-full icon
star-full icon

$200 OFF Hawaii Vacations

map-full icon

Ko Olina Resort Area, Oahu

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

Book this deal View hotel arrow-right icon
View
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. 
hotel icon
airplane icon
OUTRIGGER Reef Waikiki Beach Resort
star-full icon
star-full icon
star-full icon
star-full icon
star-half icon

$200 OFF Hawaii Vacations

map-full icon

Waikiki, Oahu

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

Book this deal View hotel arrow-right icon
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. 
hotel icon
airplane icon
Waikiki Beach Marriott Resort & Spa
star-full icon
star-full icon
star-full icon
star-full icon
star-half icon

$200 OFF Hawaii Vacations

map-full icon

Waikiki, Oahu

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

Book this deal View hotel arrow-right icon
Resort
Resort
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. 
hotel icon
airplane icon
Romer House Waikiki
star-full icon
star-full icon
star-full icon
star-half icon
star-empty icon

$200 OFF Hawaii Vacations

map-full icon

Waikiki, Oahu

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

Book this deal View hotel arrow-right icon
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. 
hotel icon
airplane icon
OUTRIGGER Waikiki Beachcomber Hotel
star-full icon
star-full icon
star-full icon
star-full icon
star-half icon

$200 OFF Hawaii Vacations

map-full icon

Waikiki, Oahu

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

Book this deal View hotel arrow-right icon
Entrance
Entrance
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. 
hotel icon
airplane icon
OUTRIGGER Waikiki Paradise Hotel
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

$200 OFF Hawaii Vacations

map-full icon

Waikiki, Oahu

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

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. 
hotel icon
airplane icon
Prince Waikiki
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

$200 OFF Hawaii Vacations

map-full icon

Waikiki, Oahu

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

Book this deal View hotel arrow-right icon
Prince Waikiki
Prince Waikiki
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. 

You will be transferred to our traditional site.

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.

You are a travel agent? Go to Pleasantagent.com. and enjoy the optimized experience for travel professionals.

support icon

Contact us

support icon

Any questions ?

Our travel advisors will be happy to help!

Call 1-800-742-9244
email icon
net.support@pleasant.net

Copied!
info icon

Are you sure you want to
delete this file?

Once deleted, you’ll need to
upload a new agreement form.