Outrigger canoe near Diamond Head, Oahu
Paddle boarding off Maui beach
Woman ziplining in Kauai rainforest
Woman eating by waterfall, Big Island 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 activities. From Waikiki to Kona experience warm waters, white sand beaches, majestic volcanoes, golf, hiking and more! Book a single island Hawaii vacation or multi island package 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 3/1/20 for travel through 12/14/20
All Deals Include: Round-trip flights, hotel accommodations, taxes and more
Waterfall, Road to Hana, Maui

Maui Vacation Deals

From the Lahaina harbor to the shores of Big Beach in Makena, Maui is excitingly diverse. Watch a humpback whale breach the sea. Tee off at a championship golf course. Drive the 53-mile jungly road to Hana or traverse the moonlike volcanic crater ofHaleakala. Or just unwind on the beach.

3 nights with air from $719
 
 
Diamond Head, Waikiki, Oahu

Oahu Vacation Deals

Oahu, is home to Honolulu, Hawaii's largest city. From the famous views of Waikiki beach, to the surfer's paradise of North Shore and beyond, Oahu offers an exotic fusion of Asian, Polynesian and western culture giving the island a flavor all its own.

3 nights with air from $509
 
 
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 $749
 
 
Mt. Kilauea Hawaii National Park

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 and rainforests 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 $675
 
 
Molokai Island Hawaii

Molokai Vacation Deals

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.

 
 
Manele Golf Course overlooking cliff, Lanai

Lanai Vacation Deals

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 - Hot Deals FREE 3-Day Hertz Car Rental offer: Valid on new bookings made 01/13/2020 – 03/01/2020 for travel 01/13/2020 – 12/14/2020. 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 San Francisco (SFO) to Maui and Oahu, Oakland (OAK) to Kauai and Los Angeles (LAX) to Island of Hawaii, and are per person, based on double occupancy. Advertised vacation rate(s) valid for departures 3/2/20.
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.]