Filter your search
Filter your search
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Hawaii, Honolulu, Oahu
Outrigger Waikiki Beach ResortSave up to 25%
Book a flight + hotel package and save up to 25% on hotel stay. Hotel savings vary depending on date of travel. Book by 8/3/20 by 6:00 p.m. CT. Like this deal, but want more flexibility? Look for the Search More Options link to change your length of stay.
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Hawaii, Big Island
Sheraton Kona Resort Spa at Keauhou BeachSave up to 30%
Book a flight + hotel package and save up to 30% on hotel stay. Hotel savings vary depending on date of travel. Book by 8/3/20 by 6:00 p.m. CT. Like this deal, but want more flexibility? Look for the Search More Options link to change your length of stay.
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Hawaii, Maui
Sheraton Maui Resort SpaSave up to 30%
Book a flight + hotel package and save up to 30% on hotel stay. Hotel savings vary depending on date of travel and room category. Book by 8/3/20 by 6:00 p.m. CT. Like this deal, but want more flexibility? Look for the Search More Options link to change your length of stay.
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Hawaii, Honolulu, Oahu
Hilton Hawaiian Village Waikiki Beach ResortSave up to 45%
Book a flight + hotel package and save up to 25% on hotel stay. Hotel savings vary depending on date of travel. Hotel offer valid in select room categories. Book by 8/3/20 by 6:00 p.m. CT. Like this deal, but want more flexibility? Look for the Search More Options link to change your length of stay.
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Hawaii, Kauai
Sheraton Kaua'i Coconut Beach ResortRoom upgrade + 50% off resort fee
Book a flight + hotel package and receive a guaranteed room upgrade from Standard View to Ocean View. Four-night minimum stay required. Book by 8/3/20 by 6:00 p.m. CT. Like this deal, but want more flexibility? Look for the Search More Options link to change your length of stay.
Hawaii vacation deals
Southwest Vacations® has some of the very best Hawaii deals available. With spectacular accommodations in a variety of cities across the Hawaiian Islands, you can design your dream trip to the Aloha state with style and budget in mind.
Book any of the great Hawaii vacation deals we offer and save because bags fly free®† with Southwest Vacations. And before you book, learn more about Southwest Vacations' exclusive Hawaii vacation packages. Explore some of the featured Hawaii resort hotels and get inspired with an array of attractions, activities, and more.
†First and second checked bags. Weight and size limits apply. A golf bag can be substituted for one checked bag.
Seats are limited and may not be available on some flights that operate during peak travel times and holiday periods. Flight and hotel rates may vary by day of week. Hotel surcharges may apply to weekends, holidays, and convention periods. Flights available on published scheduled service only. Rates may be subject to change until purchased. Discounts are valid per reservation before taxes are applied. Offer not valid on existing reservations and may not be combined with any other offer. Subject to availability. Restrictions apply. ALG Vacations Corp. is the tour operator for Southwest Vacations®.