Diamond Head Oahu

Oahu Vacation Packages

from $495
 
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 gives Oahu a flavor all its own.
 

EXCLUSIVE $100 OFF per booking

  • On minimum 3-night vacation packages
  • Book by 10/28/18 for travel through 6/30/19
All Deals Include: Round-trip airfare, 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
    • Exclusive $100 Off per booking
    • Reduced rates
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $492+

    San Francisco, California (SFO) departures, valid for travel 12/03/18

  • 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.

    • Kaiulani
    • Exclusive $100 Off per booking
    • Reduced rates
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $582+

    San Francisco, California (SFO) departures, valid for travel 12/03/18

  • 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.

    From its urban-Hawaiian beach theme to its vibrant tropical colors and unique decor, this hotel across from Waikiki Beach is fun and full of life.

    • Partial Ocean View
    • Exclusive $100 Off per booking
    • Reduced rates
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $592+

    San Francisco, California (SFO) departures, valid for travel 12/03/18

  • 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 - King Bed
    • Exclusive $100 Off per booking
    • Connecting rooms available upon request
    • Kids 17 & younger stay FREE

    3 nights with flight from $637+

    San Francisco, California (SFO) departures, valid for travel 12/03/18

  • 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 relaxed family-oriented resort is set in a quiet neighborhood close to Waikiki Beach.

    • One Bedroom Standard
    • Exclusive $100 Off per booking
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $639+

    San Francisco, California (SFO) departures, valid for travel 12/03/18

  • 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 lively hotel, just across the street from Waikiki Beach. offers contemporary comfort, camaraderie and fun.

    • Waikiki View King
    • Exclusive $100 Off per booking
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $656+

    San Francisco, California (SFO) departures, valid for travel 12/03/18

  • 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.

    • City View King
    • Exclusive $100 Off per booking
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $664+

    San Francisco, California (SFO) departures, valid for travel 12/03/18

  • 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 landmark resort offers some of the best views in Waikiki. Spacious rooms reflect the colors and ambiance that is uniquely Hawaii.

    • City View
    • Exclusive $100 Off per booking
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $690+

    San Francisco, California (SFO) departures, valid for travel 11/26/18

  • 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.

    Traditional Hawaiian elegance meets contemporary Island style at this hotel on Waikiki Beach.

    • City View King
    • Exclusive $100 Off per booking
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $691+

    San Francisco, California (SFO) departures, valid for travel 12/03/18

  • 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.

    Ilikai Hotel & Luxury Suites is a historic high-rise set above the spectacular Waikiki shoreline.

    • Luxury Mountain View
    • Exclusive $100 Off per booking
    • Reduced rates
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $697+

    San Francisco, California (SFO) departures, valid for travel 12/03/18

  • 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 on the best stretch of Waikiki beach, this trendy, sophisticated resort ushers in a new level of style to the Waikiki scene.

    • Standard
    • Exclusive $100 Off per booking
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $719+

    San Francisco, California (SFO) departures, valid for travel 12/03/18

  • 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 newly renovated 4.5 star family friendly resort is across from Waikiki Beach within easy walking to nearby shops, restaurants, and attractions. Rooms feature furnished balconies with ocean, Diamond Head, or city views.

    • Partial Ocean View King
    • Exclusive $100 Off per booking
    • Connecting rooms available upon request
    • Kids 17 & younger stay FREE

    3 nights with flight from $731+

    San Francisco, California (SFO) departures, valid for travel 12/03/18

  • 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
    • Complimentary lei greeting and welcome Moana Elixir
    • 15% spa discount
    • Daily Beach Club access for up to two people per room
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $745+

    San Francisco, California (SFO) departures, valid for travel 12/03/18

  • 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
    • Daily breakfast buffet at Surf Lanai Restaurant for up to two people per room
    • 15% spa discount
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $763+

    San Francisco, California (SFO) departures, valid for travel 12/03/18

  • 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 exclusive condominium resort offers personalized service and contemporary island-style furnishings.

    • One Bedroom Ocean View
    • Exclusive $100 Off per booking
    • Reduced rates
    • Complimentary valet parking for one car per room
    • FREE Wi-Fi
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $1037+

    San Francisco, California (SFO) departures, valid for travel 12/03/18

Hawaii - $100 OFF per booking offer: Valid on new bookings made 8/27 - 10/28/18 for travel 8/27/18 - 6/30/19. Minimum 3 nights' hotel accommodation at participating resort and roundtrip transpacific airfare required. Discount is 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.]