Hawaii Island

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We are the travel company of choice to Hawaii. We've been voted the "Best Tour Operator to Hawaii" for 15 consecutive years serving thousands of travelers annually. We know Hawaii better than anyone else so let up help plan the perfect Hawaii dream vacation or honeymoon.

Experience the best of Hawaii when you book with us:

  • Guaranteed lowest hotel prices on 4 islands+ added values
  • 200+ hotels, vacation rentals, condos and private homes on 6 islands
  • Hawaii inter-island flights, multi-island itineraries and ferry service
  • 60 Certified Hawaii Destination Specialists Reservations Agents for expert assistance
  • More than 100 friendly and professional staff in Hawaii on 4 islands
  • 900+ sightseeing tours, ziplines, luaus, activities and events
  • NCL Hawaiian Islands Cruises year-round from Honolulu visiting 4 islands
  • Fresh flower airport lei greeting upon arrival in Honolulu, Maui, Kauai and Island of Hawaii
  • Airport transfers and Hertz car rentals including convertibles, SUV's, Minivans with unlimited mileage
  • Exclusive Pleasant Holidays Hertz check-in at Hawaii airport locations for convenience
  • Travel protection coverage for peace of mind

Book online or call our travel experts at 800-742-9244

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Waterfall near road to Hana, Maui


Known for its magical ambiance, stroll the beaches of Wailea, discover the waterfalls of the Iao Valley, explore the Road to Hana or watch the sunset (or sunrise) from Haleakala.

North Shore Waves, Oahu


The most popular island for travelers, surf famous Waikiki Beach, explore the North Shore's world-class waves, snorkel Hanauma Bay and visit the USS Arizona Memorial in Pearl Harbor.

Rainbow in Kauai


Aptly named the Island of Discovery, explore the Wailua River valley, experience the grandeur of Waimea Canyon, sail the Napali Coast or splash in Hanalei Bay.

Big Island of Hawaii beach

Island of Hawaii

Explore a range of climate zones from snow-capped Mauna Kea to Waipio Valley and the Kohala Coast. Hike Kilauea or visit the black sands of Punalu'u Beach.

Manele Bay, Kauai


Those seeking peace, tranquility and an escape from big city life will find solace and serenity on Lanai. Originally, an island-wide pineapple plantation, Lanai is now know for quiet beauty and luxurious Four Seasons Resort Lanai, a private paradise with an 18-hole championship golf course and world-class spa. The perfect location for a private romantic getaway or honeymoon vacation.

Molokai View


Hawaii's fifth largest island, Molokai is home to the highest sea cliffs in the world, the longest continuous fringing reef, and pristine beaches known for their natural beauty and seclusion. Molokai does not have a major resort and is best enjoyed by those seeking a rustic vacation experience.

Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]