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5274+ Wailea Beach Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Wailea Beach

Discover more than 5274 holiday rentals in Wailea Beach. Rent By Owner holiday homes has everything you need to find a place to stay near Wailea Beach, HI.

Whether you are looking for luxury villas in Wailea Beach, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartment for family holidays, or stylish accommodation for a business trip, 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.

If you are planning to travel to Wailea Beach with a whole family or group, RBO holiday accommodations make your trip memorable. We have plenty of places to stay in Wailea Beach for families, large parties, or private owner accommodations for long or short trips. Wailea Beach Pet-friendly holiday rentals are available. Book your favorite vacation rentals in Wailea Beach with Rent By Owner. RBO makes it easy to compare and book holiday rentals today.

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Frequently Asked Questions About Wailea Beach Holiday Rentals

There are a lot of options in Wailea Beach. If you plan on staying in the Wailea Beach 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 Beach:

There are many holiday rentals available in Wailea Beach; however, here are a few of the most popular holiday homes listed in Wailea Beach on our website:
At Rent By Owner most of our places to stay are perfect for families. Check out the complete list of holiday homes in Wailea Beach to find one that works for you.
Yes, there are 5274 self-catering family homes and holiday rentals in Wailea Beach.
There are more than 5274 luxury holiday homes in or near Wailea Beach, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: