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!

Time to Celebrate With our Best Offers on Hawaii Vacations
EXCLUSIVE Guaranteed Lowest hotel rates, room upgrades, FREE breakfast offers and more

  • Book by 01/12/25 for select travel through 01/03/26

Plan Your Next Vacation With the Hawaii Experts

Pleasant Holidays is proud and honored to be voted the Best Tour Operator—Hawaii for the 20th consecutive year at the 2023 Travel Weekly Readers Choice Awards
Travel Age West Hawaii 2023Travel Weekly Readers Choice Awards 2023 - Best Tour Operator, Hawaii
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.

 
 
Hawaii Best Offers: Valid on new bookings made 11/18/24 – 01/12/25 for select travel 11/18/24 – 01/03/26 unless otherwise stated. Offers vary by hotel and travel dates, and may be category-specific, require advance booking, be restricted to specific days of the week and/or require a minimum night stay. Booking and travel dates vary by hotel. Certain restrictions and blackout dates may apply. Subject to availability. This entire offer is based on availability and can be modified or closed out at any time.
Guaranteed Lowest Hotel Rates for 2025 Hawaii Vacation Packages: Valid on new bookings at select properties for travel through 01/03/26. All offers require inclusion of roundtrip transpacific air and accommodations in select room categories. Certain restrictions and blackout dates may apply. All offers and programs apply to a limited number of rooms, and are subject to availability, change or cancellation without notice.
Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]