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83+ Upcountry Maui Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Upcountry Maui

Discover more than 83 holiday rentals in Upcountry Maui. Rent By Owner holiday homes has everything you need to find a place to stay near Upcountry Maui, HI.

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

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Frequently Asked Questions About Upcountry Maui Holiday Rentals

There are a lot of options in Upcountry Maui. If you plan on staying in the Upcountry Maui 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 Upcountry Maui:

There are many holiday rentals available in Upcountry Maui; however, here are a few of the most popular holiday homes listed in Upcountry Maui 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 Upcountry Maui to find one that works for you.
Yes, there are 83 self-catering family homes and holiday rentals in Upcountry Maui.
There are more than 83 luxury holiday homes in or near Upcountry Maui, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: