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97+ Kent Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Kent

Discover more than 97 holiday rentals in Kent. PickleTrip™ holiday homes has everything you need to find a place to stay near Kent, IL.

Whether you are looking for luxury villas in Kent, 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 Kent with a whole family or group, PickleTrip™ holiday accommodations can make your trip more memorable. We have plenty of places to stay in Kent 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 Kent with PickleTrip™. Stay and play pickleball when you travel.

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Frequently Asked Questions About Kent Holiday Rentals

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

There are many holiday rentals available in Kent; however, here are a few of the most popular holiday homes listed in Kent on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in Kent to find one that works for you.
Yes, there are 97 self-catering family homes and holiday rentals in Kent.
There are more than 97 luxury holiday homes in or near Kent, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 97 pet friendly rentals that are available in Kent.