Hawaii Deals

Hawaii Travel Packages

 from $619
Enjoy Hawaiian travel packages and vacations in the world's greatest Polynesian playground. Set in one of the most pristine and remote locations on the planet, Hawaii offers unique culture, resort accommodations and a variety of vacation activities. From Waikiki to Kona experience warm ocean waters, white sand beaches, majestic volcanoes, golf, hiking and more! Book your Hawaiian vacation package today!
Waikiki Beach

Oahu Vacation Deals

Oahu, "The Gathering Place", is home to Honolulu, Hawaii's largest city. Waikiki dazzles with its classic beaches, exciting nightlife and world-class cuisine. From the surfer's paradise of North Shore, home of the Banzai pipeline and lush rain-forests, to Pearl Harbor, steeped in history with its WWII memorials and ships, Oahu offers a fusion of Asian, Polynesian and western culture giving the island a flavor all its own.

3 nights with air from $619
Road to Hana Maui

Maui Vacation Deals

Maui has been rated one of the world's most romantic islands. With its beautiful beaches and luxury resorts, couples find a wide range of activities. From the lush "Road to Hana", to breathtaking beaches, to whale watching, luaus and gourmet cuisine, it's no wonder why Maui is a top honeymoon destination. Book your Maui vacation today.

3 nights with air from $679
Napali Coast Kauai

Kauai Vacation Deals

Known as the "Garden Isle" due to its lush tropical rain-forests and abundant flowers, Kauai is the oldest Island in the Hawaiian archipelago. It's exotic landscapes range from the stunning beaches of Princeville to breathtaking Waimea Canyon and has provided locations for such films as Blue Hawaii, Raiders of the Lost Ark, and Jurassic Park.

3 nights with air from $679
Big Island

Hawaii Island Vacation Deals

Hawaii - commonly called the Big Island - is the largest island in the Hawaiian chain. Geographically it's the most diverse. From scenic beaches, to jungle, to majestic volcanoes and snow-capped mountains, the Island of Hawaii is truly an Island of Adventure. Book your Hawaii travel package today.

3 nights with air from $679
Hawaii Cruise

Hawaii Cruise Deals

Enjoy Hawaiian Cruise Vacations offering various islands and ports in Hawaii.


Enjoy Hawaiian Vacations with Pleasant Holidays

Founded in 1959, Pleasant Holidays is one of the largest tour operators in the U.S., offering vacation packages, flights, hotels, cruises, car rentals, travel protection and related travel services to the world’s most popular destinations including Hawaii.
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.]