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 Sale
$150 OFF per Booking

  • Book by 03/01/26 for select travel through 12/15/26
  • 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.

    Family-friendly resort steps from Waikiki Beach, walkable to shops and dining. Rooms feature balconies with ocean, Diamond Head or city views. Guests enjoy Longboard Club access and ‘Alohilani hospitality.

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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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  • Aulani, A Disney Resort & Spa
    Aulani, A Disney Resort & Spa
    Ko Olina Resort Area, Oahu Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

    Inspired by the wonders and traditions of Hawaii, this resort has been uniquely designed for families. Accommodation options include spacious rooms, one- and two-bedroom suites.

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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.

    Located oceanfront in the heart of Waikiki Beach and framed by iconic Diamond Head, this smoke-free Honolulu resort features the Queensbreak Rooftop Pool & Cabana Deck.

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  • Romer House Waikiki
    Romer House Waikiki
    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.

    Romer House Waikiki is a modern surf lodge in the heart of Waikiki, a short walk from the beach. Guests can enjoy contemporary rooms, an outdoor pool and sundeck, 24-hour front desk, plus Japanese dining at 855-Aloha, and lively bars and lounges.

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  • OUTRIGGER Waikiki Beachcomber Hotel
    OUTRIGGER Waikiki Beachcomber Hotel
    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.

    Steps from the beach, Hawaii's only handcrafted Hotel in the Heart of Waikiki. Curated by local artists and influencers, inspiring beach, culture, and art. Infused stylish hotel rooms and suites with unique personality and culture of the island.

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  • OUTRIGGER Waikiki Paradise Hotel
    OUTRIGGER Waikiki Paradise Hotel
    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.

    Discover the new OUTRIGGER Waikiki Paradise Hotel, a reimagined retreat set upon royal estate grounds once known as a "paradise garden."

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  • DoubleTree by Hilton Alana Waikiki Beach
    DoubleTree by Hilton Alana Waikiki Beach
    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.

    This intimate boutique hotel is set at the gateway to Waikiki, just a short walk from the beach, and offers suites and tastefully appointed rooms.

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  • Hilton Garden Inn Waikiki Beach
    Hilton Garden Inn Waikiki Beach
    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.

    Hilton Garden Inn Waikiki Beach is two blocks from the beach and near shopping, dining, and attractions. Guests enjoy a restaurant, bar, grab-and-go options, and rooms with city or ocean-view balconies.

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Hawaii Hot Deals $150 OFF per Booking Offer: Valid on new bookings made 01/05/2026 – 03/01/2026 for select travel 01/05/2026 – 12/15/2026 unless otherwise stated. Minimum 5-night hotel accommodations at participating property and round-trip airfare required. Savings 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.
Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]