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 Airlines, Hawaiian Airlines and United Airlines
  • Inter-island flights on Hawaiian Airlines for multi-island itineraries

FREE 3-day midsize Hertz car rental

Value of midsize car may be applied to car upgrade
Exclusive check-in at Hawaii airports

Minimum 3-night vacation packages
Book by 2/24/19 for travel through 12/14/19
All Deals Include: Round-trip flights, hotel accommodations, taxes and more
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  • 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
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental
    • Daily $15 per person food & beverage credit towards breakfast at 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
    • Honeymoon amenities available

    3 nights with flight from $926+

    Oakland, California (OAK) departures, valid for travel 03/11/19 - 03/14/19
    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
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental
    • $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
    • Honeymoon amenities available

    3 nights with flight from $795+

    Oakland, California (OAK) departures, valid for travel 03/11/19 - 03/14/19
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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.

    • Tower City
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental
    • 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
    • Honeymoon amenities available

    3 nights with flight from $814+

    Portland, Oregon (PDX) departures, valid for travel 03/11/19 - 03/14/19
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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.

    • Garden/Mountain View
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental
    • 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 $665+

    Oakland, California (OAK) departures, valid for travel 03/11/19 - 03/14/19
    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
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental
    • Daily breakfast buffet at Surf Lanai Restaurant for up to two people per room
    • 15% spa discount
    • Kids 17 & younger stay FREE
    • Honeymoon amenities available

    3 nights with flight from $904+

    San Diego, California (SAN) departures, valid for travel 03/11/19 - 03/14/19
    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 Garden View or Ocean View accommodation. Valid on new bookings for select travel through 1/2/19.
Hawaii - FREE 3-Day Hertz Car Rental offer: Valid on new bookings made 1/7 - 2/24/19 for travel 1/7 - 12/14/19. Minimum 3 nights' hotel accommodation at participating resort and roundtrip airfare required. Bookings receive FREE a 3-day midsize car rental; additional car rental days may be added at additional rate. Value of 3-day midsize car rental may be applied to upgraded car classes, but may not be redeemed for cash or discounted off the vacation package price. Age restrictions may apply for car rental.
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.]