553+ Wailea, HI Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Wailea

Discover more than 553 holiday rentals in Wailea. HawaiiVillas offers everything you need to find a place to stay near Wailea, HI.

Whether you're seeking luxury villas, furnished homes, unique condos, cozy cottages for a romantic getaway, spacious apartments for family holidays, or stylish accommodations for business trips, we can help you find the perfect place. Our holiday rentals include top amenities such as indoor/outdoor swimming pools, kitchen facilities, gyms, hot tubs, internet connectivity, and more.

Planning a trip to Wailea with family or a group? HawaiiVillas holiday accommodations ensure a memorable experience. We offer plenty of options for families, large parties, or private owner accommodations for short or long trips. Wailea Pet-friendly holiday rentals are also available. Book your favorite vacation rentals in Wailea with HawaiiVillas. Easily compare and book holiday rentals today.

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Frequently Asked Questions About Wailea Holiday Rentals

There are a lot of options in Wailea. If you plan on staying in the Wailea area, consider making a reservation for a few nights at one of these properties as these have been rated the top Holiday Home Rentals in Wailea:

There are many holiday rentals available in Wailea; however, here are a few of the most popular holiday homes listed in Wailea on our website:

At Hawaii.Villas most of our places to stay are perfect for families. Check out the complete list of holiday homes in Wailea to find one that works for you.

Yes, there are 553 self-catering family homes and holiday rentals in Wailea.

There are more than 553 luxury holiday homes in or near Wailea, according to 2026 data from Hawaii.Villas. Consider these homes for your next holiday:

Yes, there are 553 pet friendly rentals that are available in Wailea.