100+ Southwest Side Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Southwest Side

Discover more than 100 holiday rentals in Southwest Side. Casai holiday homes have 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 apartments for family holidays, or stylish accommodations 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, Casai holiday accommodations will 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 Casai. Casai makes it easy to compare and book holiday rentals today.

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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 Casai.com 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 100 self-catering family homes and holiday rentals in Southwest Side.
There are more than 100 luxury holiday homes in or near Southwest Side, according to 2025 data from Casai.com. Consider these homes for your next holiday:
Yes, there are 100 pet friendly rentals that are available in Southwest Side.