Hawaii Holiday Vacations

Hawaii Holiday Season Travel

 
Picture-perfect beaches and balmy weather make Hawaii the perfect place to spend the holidays. What's more, the festive season brings several unique and memorable events to life. From Maui's one-of-a-kind Turkey Trot race to magical Honolulu City Lights and Kaua's Old-TIme Gathering celebrating traditional American and Hawaiian music, you'll find plenty to make your Hawaii vacation a memorable one.
  • The Twin Fin
    The Twin Fin
    Waikiki, Oahu Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

    Affording stunning views of iconic Diamond Head and steps from Waikiki Beach, this lively hotel with an urban-Hawaii vibe invites guests to embrace the Aloha Spirit with daily activities, regional cuisine and live entertainment.

    Book Now
  • Waikiki Beach Marriott Resort & Spa
    Waikiki Beach Marriott Resort & Spa
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Treat yourself to a luxury escape in Honolulu at this beachfront hotel with unparalleled service, thoughtful amenities and sweeping views of the Pacific Ocean.

    Book Now
  • Aston Kaanapali Shores
    Aston Kaanapali Shores
    Kaanapali Our 3.5-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Located oceanfront on Kaanapali Beach, this oceanfront full-service condominium resort combines the comfort and convenience of spacious suites with full kitchens and hotel-caliber services.

    Book Now
  • Waikoloa Beach Marriott Resort & Spa
    Waikoloa Beach Marriott Resort & Spa
    Waikoloa Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Set along the sun-drenched Kohala Coast, this elegant oceanfront resort offers modern amenities, private lanais and a pool complex with waterslide. It's the ideal getaway for couples and families.

    Book Now

Guaranteed Lowest Hotel Rates for 2025 Hawaii Vacation Packages: Valid on new bookings for travel through 01/03/26 for Alohilani Waikiki Beach Resort, The Twin Fin and Waikoloa Beach Marriott Resort & Spa; and through 12/31/25 for the Aston Kaanapali Shores. All offers require inclusion of roundtrip transpacific air and accommodations in select room categories noted above. Certain restrictions and blackout dates may apply. All offers and programs apply to a limited number of rooms, and are subject to availability, change or cancellation without notice.

Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]