2018 Hawaii Vacations

The Guaranteed Lowest Hotel Prices for Travel January - December 2019

Enjoy the best deals on Hawaii vacation packages on Oahu, Maui, Kauai and Hawaii's Big Island.
  • Exclusive reduced room rates at oceanfront resorts
  • Spa discounts, daily breakfast or food and beverage credits
  • Kids stay FREE offers
  • Private fares to Hawaii on American Airlines, Alaska Airlines, Delta Air Lines, Hawaiian Airlines and United Airlines
  • Inter-island flights on Hawaiian Airlines for multi-island itineraries

EXCLUSIVE $100 OFF per booking

  • Minimum 3-night vacation packages
  • Book by 6/2/19 for travel through 12/14/19
All Deals Include: Round-trip flights, hotel accommodations, taxes and more
  • Grand Wailea, A Waldorf Astoria Resort
    Grand Wailea, A Waldorf Astoria Resort
    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
    • Exclusive $100 OFF per booking
    • Daily $15 per person food & beverage credit towards breakfast at Cafe Kula or Grand Dining Room for ages 18 & older
    • 15% off spa services

    3 nights with flight from $892+

    San Jose, California (SJC) departures, valid for travel 08/26/19 - 08/29/19
    See Details
  • Kauai Marriott Resort
    Kauai Marriott Resort
    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
    • Exclusive $100 OFF per booking
    • $50.00 food & beverage credit per room per stay
    • 10% discount at Alexander Day Spa and Salon

    3 nights with flight from $734+

    San Jose, California (SJC) departures, valid for travel 08/26/19 - 08/29/19
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  • 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
    • Exclusive $100 OFF per booking
    • 15% spa discount
    • Daily Beach Club access for up to two people per room

    3 nights with flight from $686+

    San Jose, California (SJC) departures, valid for travel 08/26/19 - 08/29/19
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  • Sheraton Kona Resort and Spa at Keauhou Bay
    Sheraton Kona Resort and Spa at Keauhou Bay
    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
    • Exclusive $100 OFF per booking
    • Daily continental breakfast for two
    • 15% off Ho'ola Spa services

    3 nights with flight from $602+

    San Francisco, California (SFO) departures, valid for travel 08/26/19 - 08/29/19
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  • 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
    • Exclusive $100 OFF per booking
    • Daily breakfast buffet at Surf Lanai Restaurant for up to two people per room
    • 15% spa discount

    3 nights with flight from $768+

    San Jose, California (SJC) departures, valid for travel 08/26/19 - 08/29/19
    See Details
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 Pool View or Ocean View room accommodation. Valid on new bookings for select travel through 1/2/20. Food and beverage credit valid at Kukui’s on Kalapaki Beach, Aupaka Terrace or Toro Tei Sushi Bar. Credit may not be applied toward room rate, tax, resort fee, parking or any other charges. Unused credits are non-refundable and have no cash value. Spa and salon services must be booked upon arrival.
Hawaii - Hot Deals EXCLUSIVE $100 OFF per booking offer: Valid on new bookings made 4/29 - 6/2/19 for travel 4/29 - 12/14/19. Minimum 3 nights' hotel accommodation at participating resort and roundtrip airfare required.
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.]