Vacation Deals
  • 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 2023
  • 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.
    Maui Vacation Packages
    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.
    Maui Vacation Packages
  • 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.
    Oahu Vacation Packages
    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.
    Oahu Vacation Packages
  • 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.
    Kauai Vacation Packages
    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.
    Kauai Vacation Packages
  • 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.
    Big Island Vacation Packages
    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.
    Big Island Vacation Packages