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.
 

Hawaii's Best Deals

  • Up to 60% OFF room rates
  • Buy One Activity, Get One for 60% OFF
  • FREE shared airport transfers to all Waikiki hotels
  • Book by 1/13/19 for travel through 12/31/19
All Deals Include: Round-trip airfare, Hotel accommodations, Taxes and more
  • Ohia Waikiki Hotel
    Ohia Waikiki Hotel
    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
    • Hawaii Vacation Sale - Up to 60% OFF on room rates in honor of Pleasant Holidays 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $654+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
  • Sheraton Princess Kaiulani
    Sheraton Princess Kaiulani
    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
    • Hawaii Vacation Sale - Up to 60% OFF on room rates in honor of Pleasant Holidays 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $686+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
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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.

    • City View King
    • Hawaii Vacation Sale - Up to 60% OFF on room rates in honor of Pleasant Holidays 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $780+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
  • Sheraton Waikiki
    Sheraton Waikiki
    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
    • Hawaii Vacation Sale - Up to 60% OFF on room rates in honor of Pleasant Holidays 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $821+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
  • 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.

    • Resort View
    • Hawaii Vacation Sale - Up to 60% OFF on room rates in honor of Pleasant Holidays 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)
    • Connecting rooms available upon request
    • Kids 17 & younger stay FREE

    3 nights with flight from $830+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
  • Hyatt Regency Waikiki Beach Resort and Spa
    Hyatt Regency Waikiki Beach Resort and 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.

    • Waikiki View King
    • Hawaii Vacation Sale - Up to 60% OFF on room rates in honor of Pleasant Holidays 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)
    • Connecting rooms available upon request
    • FREE Wi-Fi
    • Kids 18 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $841+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
  • 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.

    This landmark resort offers some of the best views in Waikiki. Spacious rooms reflect the colors and ambiance that is uniquely Hawaii.
    • City View
    • Hawaii Vacation Sale - Up to 60% OFF in honor of our 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $861+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
  • Moana Surfrider, A Westin Resort & Spa
    Moana Surfrider, A Westin 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.

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

    • Historic Banyan
    • Hawaii Vacation Sale - Up to 60% OFF on room rates in honor of Pleasant Holidays 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)
    • 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 $875+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
  • Queen Kapiolani Hotel
    Queen Kapiolani Hotel
    Waikiki, Oahu Our 2.5-Star classification designates those properties offering comfortable accommodations with standard amenities. Guests can expect dependable services in a clean and comfortable environment. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This iconic hotel affords breathtaking views of Waikiki Beach and Diamond Head, and offers a great vacation value.
    • Standard
    • Hawaii Vacation Sale - Up to 60% OFF on room rates in honor of Pleasant Holidays 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)
    • Kids 17 & younger stay FREE

    3 nights with flight from $902+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
  • '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.

    Named among the Best Resorts in Hawaii in the 2018 Condé Nast Readers' Choice Awards, This newly renovated family-friendly resort is across from Waikiki Beach within easy walking to nearby shops, restaurants, and attractions.

    • Partial Ocean View King
    • Hawaii Vacation Sale - Up to 60% OFF on room rates in honor of Pleasant Holidays 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)
    • Connecting rooms available upon request
    • Kids 17 & younger stay FREE

    3 nights with flight from $916+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
  • The Royal Hawaiian, a Luxury Collection Resort, Waikiki
    The Royal Hawaiian, a Luxury Collection Resort, Waikiki
    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
    • Hawaii Vacation Sale - Up to 60% OFF on room rates in honor of Pleasant Holidays 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)
    • 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 $965+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
  • Turtle Bay Resort
    Turtle Bay Resort
    North Shore, 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.

    Surrounded by the beauty and majesty of O'ahu's legendary North Shore, this luxurious resort embodies the very essence of Hawaii.

    • Resort View - King bed
    • Hawaii Vacation Sale - Up to 60% OFF on room rates in honor of Pleasant Holidays 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)
    • Connecting rooms available upon request
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $1071+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
  • The Ritz-Carlton Residences, Waikiki Beach Hotel
    The Ritz-Carlton Residences, Waikiki Beach Hotel
    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.

    The Ritz-Carlton Residences, Waikiki Beach offers the ultimate in luxury with gorgeous ocean views, a full-service spa, two magnificent ocean-facing pools and much more.
    • Studio Ocean View
    • Hawaii Vacation Sale - Up to 60% OFF on room rates in honor of Pleasant Holidays 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)
    • $50 resort credit per room (valid for travel January 4 - March 31, 2019)
    • FREE Wi-Fi
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $1221+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
Hawaii - Best Deals offers: Valid on new bookings made 10/29/18 - 1/13/19 for travel 10/29/18 - 12/31/19. Accommodation at participating resort and roundtrip transpacific airfare required. Room rate savings and minimum night stay vary by participating resort. Travelers will receive a voucher valid to buy one activity and get one activity of equal or lesser value for 60% off the retail value redeemable at any Pleasant Activities Center or the Pleasant Holidays Island Orientation in Hawaii or via the Hawaii Call Center by calling 1-888-229-7770. Fees and surcharges are excluded and must be paid for both tours. Limit of one discounted activity per booking. Offer does not apply to activities involving flights (plane or helicopter). Complimentary roundtrip shared airport transfers valid to/from HNL and any Waikiki hotel or resort in Pleasant Holidays' Oahu portfolio; offer does not apply to any hotels or resorts outside of Waikiki. Activity voucher and airport transfers have no cash value, are non-transferrable, are not combinable with any other offers, apply only to the vacation on which they were booked and expire at the end of booking's travel dates. Offer subject to availability and may be changed or cancelled at any time. Certain restrictions and blackout dates may apply.
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.]