2018 Hawaii Vacations

EXCLUSIVE rates and added values on 2019 Hawaii Vacations + Festive Season Availability for 2018

Enjoy the best deals on Hawaii vacation packages on Oahu, Maui, Kauai and Hawaii's Big Island.
  • Exclusive reduced room rates
  • Spa discounts
  • Kids stay FREE offers
  • And more
All Deals Include: Round-trip airfare, Hotel accommodations, Taxes and more

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
  • Kona 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 resort is situated on the water's edge on the tranquil Keauhou Bay, a gathering place for manta rays.

    • Mountain 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)
    • Daily continental breakfast for two
    • 15% off Ho'ola Spa services
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $697+

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

  • 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
    • 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

  • 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

  • Kauai, Lihue, HI 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.

    Majestic waterfalls, blue lagoons and lush tropical surroundings distinguish this deluxe Hawaiian resort set on beautiful Kalapaki Bay.

    • Pool 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)
    • $50.00 food & beverage credit per room per stay
    • 10% discount at Alexander Day Spa and Salon
    • One-day complimentary pool cabana per room per stay
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $1017+

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

  • Wailea, Maui 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.

    Voted one of the Best Resort in Hawaii in the 2018 Condé Nast Readers' Choice Awards, this luxury Hilton beachfront resort offers spacious rooms, 9 pools, 3-story tube slide, spa, fine dining with championship golf nearby.

    • Run of House
    • 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 continental breakfast in Cafe Kula or Grand Dining Room for ages 18 & older
    • 15% off spa services
    • Complimentary lei greeting and welcome drink
    • FREE Wi-Fi
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $1045+

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

  • Kaanapali 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.

    Commanding a spectacular stretch of Kaanapali Beach, this magnificent resort offers a family-friendly getaway.

    • Mountain 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)
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $1053+

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

Rates are based on roundtrip air travel as indicated above and are per person, based on double occupancy. Additional travel dates available.
Hawaii Exclusive Savings Offers for 2018 and 2019: All offers require inclusion of roundtrip transpacific air and accommodations. Certain restrictions apply. All offers and programs are subject to availability, change or cancellation without notice. Blackout dates may apply.
Grand Wailea, A Waldorf Astoria Resort: Requires Run of House or Run of Ocean accommodations. Valid on new bookings for travel 1/4/19 – 1/3/20.
The Royal Hawaiian, a Luxury Collection Resort: Requires Historic accommodations. Valid on new bookings for travel through 1/2/20.
Moana Surfrider, A Westin Resort & Spa: Requires Banyan City, Tower Deluxe City or Diamond Deluxe Ocean accommodations. Valid on new bookings for travel through 1/2/20.
Sheraton Kona Resort & Spa at Keauhou Bay: Requires Mountain View or Ocean View accommodation. Valid on new bookings for travel through 1/4/20.
Kauai Marriott Resort: Requires Garden View or Ocean View accommodation. Valid on new bookings for select travel through 1/2/19.
The Westin Maui Resort & Spa: Requires Mountain View or Ocean View accommodation. Valid on new bookings for travel through 1/3/19.
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.]