Kihei Surfside vacation rentals

We found 67 vacation rentals — enter your dates for availability

Welcome to the enchanting shores of Kihei Surfside, where vibrant sunsets meet the turquoise waters of Wailea Beach and Keawakapu. This coastal paradise invites travelers to bask in the sun, partake in thrilling water sports, and embark on unforgettable whale-watching adventures. With a charming atmosphere perfect for families and groups, you’ll find a variety of accommodations, from cozy condos to spacious homes, offering the comfort and amenities of a true home away from home. Experience the magic of Maui in a vacation rental that enhances your getaway with space and convenience.

Find spaces that suit your style

  • Peace of mind

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
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