Why Book Pleasant Hawaiian Holidays?Since 1959, Pleasant Hawaiian Holidays has offered vacation packages to Oahu, Maui, Kauai and the Big Island, customized just for you. We're totally committed to your perfect vacation and along the way, we've earned the awards to prove it.
60 Years of ExpertiseWe started in 1959 with charter flights and hotel partnerships in the US' hottest beach destination. Since then, we've sent over 10 million people to our favorite islands. Over the years, we've expanded our portfolio worldwide through the Pleasant Holidays brand, but Hawaii has always been our passion and our heart.
Want to catch the famous cliffs of Kauai up close from a helicopter? Our activity specialists can make that happen. Just landed on Maui and don't know where to start? Don't worry, we've got it covered. Our Pleasant Activities desks in Hawaii are staffed by local experts who can help you choose from over 1,000 unique experiences.