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!
Get Ready for HAWAII
Welcoming Visitors Starting August 1, 2020
  • Travelers are required to present proof of a negative COVID-19 test within 72 hours of travel
  • Travelers without proof of a negative COVID-19 test will be required to quarantine for 14 days

Hawaii - FREE 5-day, two-category Hertz car rental upgrade
from midsize to luxury, convertible, Jeep or SUV

Book by 8/30/20 for travel through 4/30/21
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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 Two-Category Hertz Car Rental Upgrade Offer: Valid on new bookings made 07/06/2020 – 08/30/2020 for travel 07/06/2020 – 04/30/2021. Roundtrip airfare and minimum 5 nights’ hotel accommodation at participating hotel required. Age restrictions apply for car rental. Upgrade is from Midsize to Convertible, Jeep, Luxury or SUV for five days.
Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]