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121+ Hawaii Kai Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Hawaii Kai

Discover more than 121 holiday rentals in Hawaii Kai. PickleTrip™ holiday homes has everything you need to find a place to stay near Hawaii Kai, HI.

Whether you are looking for luxury villas in Hawaii Kai, 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 with private pickleball courts or nearby facilities. 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 Hawaii Kai with a whole family or group, PickleTrip™ holiday accommodations can make your trip more memorable. We have plenty of places to stay in Hawaii Kai for families, large parties, or private owner accommodations for long or short trips. Pet-friendly holiday rentals are available as well. Book your favorite vacation rentals in Hawaii Kai with PickleTrip™. Stay and play pickleball when you travel.

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Frequently Asked Questions About Hawaii Kai Holiday Rentals

There are a lot of options in Hawaii Kai. If you plan on staying in the Hawaii Kai 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 Hawaii Kai:

There are many holiday rentals available in Hawaii Kai; however, here are a few of the most popular holiday homes listed in Hawaii Kai on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in Hawaii Kai to find one that works for you.
Yes, there are 121 self-catering family homes and holiday rentals in Hawaii Kai.
There are more than 121 luxury holiday homes in or near Hawaii Kai, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 121 pet friendly rentals that are available in Hawaii Kai.