214+ Old Southwest Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Old Southwest

Discover more than 214 holiday rentals in Old Southwest. PickleTrip™ holiday homes has everything you need to find a place to stay near Old Southwest, VA.

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

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Frequently Asked Questions About Old Southwest Holiday Rentals

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

There are many holiday rentals available in Old Southwest; however, here are a few of the most popular holiday homes listed in Old Southwest on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in Old Southwest to find one that works for you.
Yes, there are 214 self-catering family homes and holiday rentals in Old Southwest.
There are more than 214 luxury holiday homes in or near Old Southwest, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 214 pet friendly rentals that are available in Old Southwest.