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44+ Oak Run Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Oak Run

Discover more than 44 holiday rentals in Oak Run. PickleTrip™ holiday homes has everything you need to find a place to stay near Oak Run, IL.

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

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Frequently Asked Questions About Oak Run Holiday Rentals

There are many holiday rentals available in Oak Run; however, here are a few of the most popular holiday homes listed in Oak Run on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in Oak Run to find one that works for you.
Yes, there are 44 self-catering family homes and holiday rentals in Oak Run.
There are more than 44 luxury holiday homes in or near Oak Run, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 44 pet friendly rentals that are available in Oak Run.