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66+ Kailua (Maui) Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Kailua (Maui)

Discover more than 66 holiday rentals in Kailua (Maui). Rent By Owner holiday homes has everything you need to find a place to stay near Kailua (Maui), HI.

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

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Kailua (Maui) Holiday Homes Frequently Asked Questions

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

There are many holiday rentals available in Kailua (Maui); however, here are a few of the most popular holiday homes listed in Kailua (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 Kailua (Maui) to find one that works for you.
Yes, there are 66 self-catering family homes and holiday rentals in Kailua (Maui).
There are more than 66 luxury holiday homes in or near Kailua (Maui), according to 2025 data from Rent By Owner. Consider these homes for your next holiday: