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
  • 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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  • 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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  • 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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  • 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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  • 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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  • 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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  • North Shore, 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.

    Surrounded by the beauty and majesty of Oahu's legendary North Shore, this luxurious resort embodies the very essence of Hawaii. Enjoy expansive ocean and bay views in junior and family suites with 725 square feet accommodating up to four guests.

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  • 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, 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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  • 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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  • 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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  • 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.

    This is a historic high-rise set above the spectacular Waikiki shoreline. One- and two-bedroom city and ocean view rooms include gourmet kitchens, lanai and Wi-Fi access.

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  • 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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  • 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 exceptional value at this family-friendly hotel offering one- and two-bedroom suites with kitchenettes in the heart of Waikiki, just five minutes from the beach.

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  • 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.

    This Waikiki hotel offers beautiful city and ocean views, and is close to shopping, dining and attractions.

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  • 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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  • 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 adults-only, urban surf hotel lies close to Waikiki Beach and features convenient in-house services such as three on-site restaurants/bars, an outdoor pool, sundeck, breakfast, and 24-hour front desk.

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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.]