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 cusine. On the northen side of the island, the surfer's paradise of North Shore, home of the Banzi pipeline and scenic rainforests offers a laid back island style visitors are sure to enjoy. To the West, Pearl Harbor is steeped 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 Oahu deals on Hawaii vacation packages today!
 

EXCLUSIVE $100 OFF per booking

  • Minimum 3-night vacation packages
  • Book by 10/27/19 for travel through 6/30/20
All Deals Include: Round-trip flights, hotel accommodations, taxes and more
  • Waikiki, Oahu Our 2-Star classification designates those properties offering comfortable accommodations with standard amenities. Guests can expect dependable services in a clean and comfortable environment.

    Situated in the heart of one of the world’s most popular vacation destinations, this hotel is close to shopping, restaurants, and nightlife.

    • Hotel Room
    • Exclusive $100 OFF per booking

    3 nights with flight from $438+

    Oakland, California (OAK) departures, valid for travel 10/28/19 - 10/31/19

  • 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.

    Experience comfort and relaxation in the heart of Waikiki at this hotel while enjoying an exceptional vacation value.

    • Princess Tower City Side
    • Exclusive $100 OFF per booking

    3 nights with flight from $499+

    Oakland, California (OAK) departures, valid for travel 10/28/19 - 10/31/19

  • 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.

    • Two Doubles Standard City View Private Lanai
    • Exclusive $100 OFF per booking

    3 nights with flight from $568+

    Oakland, California (OAK) departures, valid for travel 10/28/19 - 10/31/19

  • 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 all-suite hotel offers spacious and affordable studios, one-, two- and three-bedroom suites.

    • One Room Bungalow
    • Exclusive $100 OFF per booking

    3 nights with flight from $596+

    Oakland, California (OAK) departures, valid for travel 10/28/19 - 10/31/19

  • 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.

    "Sharing the Arts & Culture of Hawaii" This distinctive, refined hotel presents a new vision of hospitality, combining timeless traditions with modern elegance.

    • Standard Two Doubles
    • Exclusive $100 OFF per booking

    3 nights with flight from $601+

    Oakland, California (OAK) departures, valid for travel 10/28/19 - 10/31/19

  • 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.

    • Resort view
    • Exclusive $100 OFF per booking

    3 nights with flight from $602+

    Oakland, California (OAK) departures, valid for travel 10/28/19 - 10/31/19

  • 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.

    "An Oasis in the Heart of Waikiki" This brand new lifestyle resort which just completed a $35 million modernization offers contemporary comfort, camaraderie and fun.

    • Waikiki View King
    • Exclusive $100 OFF per booking

    3 nights with flight from $610+

    Oakland, California (OAK) departures, valid for travel 10/28/19 - 10/31/19

  • 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.

    Just two blocks to Waikiki Beach, this relaxed family oriented condominium resort features island style living with their one- and two-bedroom accommodations with full kitchens.

    • One Bedroom Standard
    • Exclusive $100 OFF per booking

    3 nights with flight from $635+

    Oakland, California (OAK) departures, valid for travel 10/28/19 - 10/31/19

  • 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.

    “Where the Beach Comes Alive” Our extended ohana (family) will discover local beach and surf culture at this hotel on Waikiki Beach.

    • City View King
    • Exclusive $100 OFF per booking

    3 nights with flight from $651+

    Oakland, California (OAK) departures, valid for travel 10/28/19 - 10/31/19

  • 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 legendary resort, "The First Lady of Waikiki," combines turn-of the-century Victorian elegance with modern Westin amenities and luxuries.

    • Historic Banyan
    • Exclusive $100 OFF per booking
    • 15% spa discount
    • Daily Beach Club access for up to two people per room

    3 nights with flight from $683+

    Oakland, California (OAK) departures, valid for travel 10/28/19 - 10/31/19

  • Waikiki, 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.

    This legendary hotel, known as the Pink Palace of the Pacific, offers a redefined luxury experience.

    • Historic
    • Exclusive $100 OFF per booking
    • 15% spa discount
    • Daily breakfast for two

    3 nights with flight from $765+

    Oakland, California (OAK) departures, valid for travel 10/28/19 - 10/31/19

  • 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.

    Recently renovated, this exclusive condominium resort offers spacious and elegantly furnished with one and two-bedroom suites with fully-equipped chef inspired kitchens, in-room washer/dryer and ocean views.

    • Two Bedroom Ocean View
    • Exclusive $100 OFF per booking

    3 nights with flight from $1217+

    Oakland, California (OAK) departures, valid for travel 10/28/19 - 10/31/19

Hawaii - Hot Deals EXCLUSIVE $100 OFF per booking offer: Valid on new bookings made 8/26 - 10/27/19 for travel 8/26/19 - 6/30/20. Minimum 3 nights' hotel accommodation at participating resort and roundtrip airfare required. Savings is $100 per booking, taken at time of booking and reflected in rates shown.
Rates quoted are per person, based on double occupancy unless otherwise stated. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult. Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]