Diamond Head Oahu

Oahu Vacation Packages

 
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.

Hawaii Summer & Fall Savings

Room upgrades, resort credits, FREE breakfast offers, and more
  • Book by 08/24/25 for select travel through 12/31/25
  • Hilton Hawaiian Village Waikiki Beach Resort
    Hilton Hawaiian Village Waikiki Beach Resort
    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.

    Lush grounds, six spectacular pools, a beachfront lagoon, waterfalls and an array of shops and restaurants are all part of the "Village" experience at this expansive resort.

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  • OUTRIGGER Waikiki Beach Resort
    OUTRIGGER Waikiki Beach Resort
    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.

    Escape to sun, sand & surf on legendary Waikiki Beach. From the beach boys to Duke's Waikiki, experience beach life with live music and entertainment, vibrant cultural events, and accommodations overlooking iconic Waikiki Beach and Diamond Head.

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  • 'Alohilani Resort Waikiki Beach
    'Alohilani Resort Waikiki Beach
    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.

    This family-friendly resort across from Waikiki Beach is within easy walking distance of shops, restaurants, and attractions.

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  • 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.

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  • Sheraton Waikiki Beach Resort
    Sheraton Waikiki Beach Resort
    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.

    Vivid by day, vibrant by night this exceptional oceanfront resort features newly renovated rooms and suites with spectacular ocean views, award-winning outdoor pools, and Waikiki's best family-friendly location.

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  • OUTRIGGER Reef Waikiki Beach Resort
    OUTRIGGER Reef Waikiki Beach Resort
    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.

    This distinctive, refined hotel presents a new vision of hospitality, combining timeless traditions with modern elegance.

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  • Embassy Suites by Hilton Waikiki Beach Walk
    Embassy Suites by Hilton Waikiki Beach Walk
    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.

    This all-suite Waikiki resort boasts free daily breakfast, evening poolside reception, and a prime location steps from Waikiki Beach and top shopping, dining, and cultural experiences at Waikiki Beach Walk®.

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  • 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.

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  • Hyatt Regency Waikiki Beach Resort & Spa
    Hyatt Regency Waikiki Beach 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.

    Explore the excitement of Oahu in one of Hawaii’s most fashionable zip codes. Just steps from renowned warm waters and spectacular views.

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  • The Ambassador Hotel of Waikiki, Tapestry Collection by Hilton
    The Ambassador Hotel of Waikiki, Tapestry Collection by Hilton
    Waikiki, Oahu 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.

    At the gateway to Waikiki, this hotel connects guests with the creative and modern spirit of the neighborhoods of Honolulu. Centered around Waikiki’s creative culture, it’s a neighborhood hotel made for more than beach days.

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  • Waikiki Malia
    Waikiki Malia
    Waikiki, Oahu Our 3-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.

    Located in central Waikiki within walking distance of luxury shopping and many dining options, this hotel offers spacious guest rooms with tasteful accents and refined decor for an intimate, energizing, and rejuvenating getaway.

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  • Wayfinder Waikiki
    Wayfinder Waikiki
    Waikiki, Oahu Our 3-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.

    This charming retreat in the heart of world-famous Waikiki is where guests are assured a warm aloha.

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  • Aston Waikiki Sunset
    Aston Waikiki Sunset
    Waikiki, Oahu Our 3-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.

    This Waikiki haven has an easy-going island vibe and awe-inspiring views of iconic Diamond Head.

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Hawaii Summer & Fall Savings: Valid on new bookings made 06/30/2025 – 08/24/2025 for select travel through 12/31/2025 unless otherwise indicated. Valid on new bookings for select travel through 12/31/2025 unless otherwise indicated. 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.]