Hawaii Big Island

Big Island of Hawaii Vacation Packages

 
Hawaii - aka the Big Island - is nearly twice the size of all the other Hawaiian islands combined. Geographically it's the most diverse island of the archipelago, with deserts, rainforests, volcanoes and, surprisingly, snow-capped mountains.

The mountains create a barrier that blocks the northeasterly trade winds, making the western side of the island the driest region in the archipelago. This coast has the best beaches and water conditions. The eastern coast is rugged, with pounding surf, tropical rainforests and majestic waterfalls.
 

60th Anniversary Hawaii Vacation Sale

  • Up to 60% OFF room rates
  • Buy One Activity, Get One for 60% OFF
  • Book by 1/13/19 for travel through 12/31/19
All Deals Include: Round-trip airfare, Hotel accommodations, Taxes and more
  • Royal Kona Resort
    Royal Kona Resort
    Kona 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 oceanfront resort offers remodeled rooms, a private beach cove and swimming lagoon, just a short walk from historic Kailua-Kona.

    • 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)
    • Connecting rooms available upon request
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $665+

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

    Nestled amid swaying palms and overlooking the glistening blue Waiulua Bay, this oceanfront resort blends contemporary facilities with graceful Hawaiian culture.
    • Ocean Tower 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)
    • Kids 18 & younger stay FREE

    3 nights with flight from $781+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
  • Waikoloa Beach Marriott Resort & Spa
    Waikoloa Beach Marriott Resort & Spa
    Waikoloa 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.

    Set along the sun-drenched Kohala Coast, this contemporary resort is the ideal getaway for couples and families.
    • Resort View - Garden/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)
    • Connecting rooms available upon request
    • Kids 17 & younger stay FREE

    3 nights with flight from $882+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
  • The Westin Hapuna Beach Resort
    The Westin Hapuna Beach Resort
    Hapuna Beach 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 luxurious hotel, set on the sunny Kohala Coast, features all ocean-facing accommodations affording panoramic vistas and contemporary Hawaiian style..

    • Partial 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)
    • Connecting rooms available upon request
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $1101+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
Hawaii - 60th Anniversary Hawaii Vacation Sale: 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.]