• Home
  • Vacation Deals
  • Vacation Rentals
  • Cruises
  • Destinations
  • All-Inclusive
  • Group Travel
  • Pleasant Activities
  • Travel Agent Sign In
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!
  • See All Vacations

Hot Deals: Hawaii

  • Book by 06/29/25 for select travel through 12/15/25

Plan Your Next Vacation With the Hawaii Experts

Pleasant Holidays is proud and honored to be voted the Best Tour Operator—Hawaii for the 21st consecutive year at the 2024 Travel Weekly Readers Choice Awards
Travel Age West Hawaii 2024

  • 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
1-800-742-9244
  • Hawaii $150 OFF per Booking Offer: Valid on new bookings made 05/05/2025 – 06/29/2025 for select travel 05/05/2025 – 12/15/2025. Minimum 5-night hotel accommodations at participating property and roundtrip airfare required. Savings is per booking and taken at time of booking. This entire offer is based on availability and can be modified or closed out at any time.
  • Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]
  • Terms & Conditions
  • Privacy Statement
  • User Agreement
  • Travel Protection Plans
  • Cruise Protection Plans
  • Careers
  • Full site
Copyright © 1999-2025 Pleasant Holidays, LLC. All rights reserved. Pleasant Holidays and the Pleasant Holidays logo are registered trademarks of Pleasant Holidays, LLC.
CST # 1007939-10. UBI# 601 915 263. TAR#5308. Florida ST#37983.

Session info

Session id: