Oahu
Maui
Kauai
Island of Hawaii

Hawaii Vacation Packages

 
Hawaii is hiking sculpted cliffs or diving amidst coral reefs in the afternoon and dining to slack-key guitar at sunset. The fresh, floral air energizes you. The warm, tranquil waters refresh you. The breathtaking beauty renews you. Year-round gentle weather surrounds you on every island. With soft breezes, towering cliffs and cavorting whales, the Islands are rich with natural wonders. Look around. There's no place on earth like Hawaii. We warmly invite you to explore these scenic islands for an idyllic travel experience.

Enjoy the aloha spirit with Hawaiian vacation packages and travel deals to the world's greatest Polynesian playground. Hawaii offers unique culture, resort accommodations and a variety of vacation activities. From Waikiki to Kona experience warm waters, white sand beaches, majestic volcanoes, golf, hiking and more! Book your Hawaii vacation today!

#LetHawaiiHappen

Six Hawaiian Islands. Six unique experiences. From crystal blue waters to stunning green cliffs
and black sand beaches, Hawaii's wealth of natural beauty is the breathtaking backdrop for
unforgettable experiences that reward those who delve a little deeper - into vibrant cultures full of
welcoming aloha, a thriving food scene and thrilling outdoor adventures.
There's so much more to Hawaii than what you've heard about. #LetHawaiiHappen
The Hawaiian Islands Logo

FREE 3-day midsize Hertz car rental

  • Minimum 3-night vacation packages
  • Book by 4/28/19 for travel through 12/14/19
All Deals Include: Round-trip flights, hotel accommodations, taxes and more
Maui

Maui

Romance is always in the air on Maui. And why shouldn’t it be? This is the best of both worlds, offering a unique blend of sophistication with a laid back, small town feel. Start your day atop the summit of Haleakalā for an epic sunrise. Spend the day along the scenic, winding road to Hāna or travel through the lush gardens and farms of Upcountry Maui.

3 nights with air from $529
 
 
Oahu

Oahu

This is where the action is. The lively center of the Hawaiian Islands. A vibrant gathering spot with a unique blend of relaxation and excitement. O‘ahu is famous for iconic Hawai‘i locations like Waikiki Beach, Pearl Harbor and the surfing mecca of the North Shore, but there’s so much more to explore

3 nights with air from $509
 
 
Kauai

Kauai

“Rejuvenating” is a word often used on Kaua‘i, known for iconic spots like the soaring cliffs of the Nāpali Coast, the panoramic views of Waimea Canyon and the peaceful currents of the Wailua River. But even more breathtaking discoveries await along Kaua‘i’s one-lane highways.

3 nights with air from $535
 
 
Hawaii Island

Island of Hawaii

Take a road trip on the biggest of the Hawaiian Islands. This is a place of stark contrasts – from the crystal blue waters and white sands of the Kona Coast, to the rugged volcanic coastlines of Hawai‘i Volcanoes National Park, to the lush botanical gardens and waterfalls of the Hāmākua Coast

3 nights with air from $625
 
 
Molokai Island Hawaii

Molokai

Natural, unspoiled and rustic, Moloka‘i remains true to its island roots. Where visitors can experience old-style Hawai‘i and feel the Hawaiian culture and aloha spirit permeate from the central town of Kaunakakai to revered Hālawa Valley and sacred Kalaupapa. Trek through Hālawa Valley.

 
 
Lanai

Lanai

Embrace serenity on the island where not one single traffic light can be found. Where luxury and privacy are a way of life. As the smallest inhabited island, Lāna'i offers an escape from it all. Indulge in world-class amenities and championship golf, or spend the morning exploring local shops in Lāna'i City.

 
 
Hawaii - FREE 3-Day Hertz Car Rental offer: Valid on new bookings made 2/25 - 4/28/19 for travel 2/25 - 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 are based on roundtrip air travel from Oakland (OAK) to the island of Hawaii, Portland (PDX) to Oahu and San Diego (SAN) to Maui and Kauai, and are per person, based on double occupancy. Advertised vacation rate(s) valid for departures 5/20/19.
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.]