Diamond Head Oahu
Maui Beach, Lanai in background
Hanalei Bay Kauai
Lava flow off of Hawaii's Big Island

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!

Hawaii Travel & Testing Guidelines

In order to avoid a mandatory 14-day quarantine, travelers to Hawaii must take a COVID-19 test within 72 hours of the final leg of their flight to Hawaii and receive proof of a negative test result prior to boarding. Travelers must complete the State of Hawaii's Safe Travels online travel and health questionnaire and upload proof or a negative COVID-19 test result within 24 hours of flight departure to Hawaii. The test must be an FDA-approved NAAT COVID-19 test taken at an approved testing facility. Children ages 4 years and under are not required to provide a pre-travel test when traveling with parents. For travel between the Hawaiian Islands, another COVID-19 test may be required within 72-hours of arrival to bypass quarantine. Interisland passengers arriving on Oahu are not required to quarantine.  More information on each island's testing requirements is available here. Testing requirements are subject to change. Gov. David Ige has extended the statewide mask mandate, which requires all persons in the State to wear a face covering over their nose and mouth when in public.

Pleasant Holidays has partnered with CVS Health, a trusted testing partner approved by the state of Hawaii to provide travelers to Hawaii with options for pre-travel COVID-19 testing at 2,800 locations across the continental U.S. Learn more and make your appointment here.

CVS

Happy Hawaii Holidays
Give the gift of travel this holiday season with discounts and extras

  • Book by 1/10/21 for travel through 6/30/21
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 of Haleakala. Or just unwind on the beach.

 
 
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.

 
 
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.

 
 
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.

 
 
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 $100 OFF per booking: Happy Hawaii Holidays: Valid on new bookings made 11/2/20 - 1/10/21 for select travel through 6/30/21. Minimum 3-night hotel accommodations at participating property and roundtrip airfare required. 
Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]