93+ Southwest Side Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Southwest Side

Discover more than 93 holiday rentals in Southwest Side. Rent By Owner holiday homes has everything you need to find a place to stay near Southwest Side, IL.

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

Show more
Show less

Frequently Asked Questions About Southwest Side Holiday Rentals

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

There are many holiday rentals available in Southwest Side; however, here are a few of the most popular holiday homes listed in Southwest Side 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 Southwest Side to find one that works for you.
Yes, there are 93 self-catering family homes and holiday rentals in Southwest Side.
There are more than 93 luxury holiday homes in or near Southwest Side, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: