Hawaii Island Vacations & Getaways

Discover an unforgettable tropical vacation in the beautiful islands of Hawaii. With its long stretches of sandy beaches, lush tropical scenery, and spectacular activities, Hawaii provides an unrivaled vacation destination. Whether it’s exotic sightseeing you seek for your family vacation or a romantic getaway for you and someone special, a Hawaiian vacation offers it all.

Top Hawaii Vacation Spots

Uplift your spirits and rejuvenate your soul in one of the most beautiful vacation destinations in the world. Classic Vacations offers one-of-a-kind luxury vacations to the Islands of Hawaii.

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The Islands of Hawaii

Big Island

The uncrowded Big Island of Hawaii fills the luxury hotels of Hawaii vacations with superlatives from snow-capped Maunakea to active Kilauea volcano. Learn More

Hotels in Big Island
The Mauna Lani Bay Hotel & Bungalows
Sheraton Kona Resort & Spa at Keauhou Bay

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Kauai

Lush Kauai sets the stage for romance and adventure during luxurious Hawaii vacations. Discover Kauai's 5 star hotels, velvet-green valleys, and dramatic waterfalls. Learn More

Hotels in Kauai
Sheraton Kauai Resort
The St. Regis Princeville Resort

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Lanai

Once famous for Hawaii pineapples, now home to two renowned luxury Hawaii hotels. Enjoy Hawaii vacations on the beach or in the highland forest. Learn More

Hotels in Lanai
Four Seasons Resorts Lanai at Manele Bay
Four Seasons Resorts Lana'i, The Lodge at Koele

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Maui

Hailed as the Valley Isle of Hawaii — Hawaii vacations to Maui are celebrated for its charming towns, luxury hotels, world-class golf, and elegant beaches. Learn More

Hotels in Maui
Grand Wailea, A Waldorf Astoria Collection
Makena Beach & Golf Resort

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Oahu

Home to Hawaii’s Waikiki beach and Honolulu city— Hawaii vacations to Oahu offer fine dining, shopping, golf, and nightlife from our luxury hotels. Learn More

Hotels in Oahu
The Kahala Hotel & Resort
Halekulani

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