Compare Vacation Rentals & Rent By Owner Homes in Southwest Side, Illinois, USA
About Southwest Side Vacation Rentals
With more than 93 Southwest Side vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Southwest Side.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Southwest Side, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Southwest Side. Places to stay near Southwest Side are 378.6 ft² on average, with prices averaging US $207 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Southwest Side with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Other Places to Stay in Southwest Side, IL
Frequently Asked Questions About Southwest Side?
What are the top vacation rentals in Southwest Side?
- Family Friendly 2-Bedroom w/Kitchen & Laundry
- 1-bedroom condo next to Chicago Midway International Airport
- Newly remodeled 3 bedroom apt, a hidden gem 20 min to almost anyplace in Chicago
- Your Home Away from home -12 mins from Downtown
- Stylish comfortable 3BR with tons of natural light
- Super Amazing Place To Stay Near Downtown! Free Parking
- Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
- Cozy 3 Bedroom Family Sized Duplex/9 mins from Midway airport!nn
- Cozy Urban Retreat Near Midway – Perfect for Travelers!
- Beautiful Home Near Downtwon - Free Parking!
How many Rentbyowner vacation rentals are available in Southwest Side?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 93 in the Southwest Side area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Southwest Side.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| Heart of Chicago Vacation Rentals in Chicago, Illinois | 27 |
| Greater Grand Crossing Vacation Rentals in Chicago, Illinois | 471 |
| Bridgeport Vacation Rentals in Chicago, Illinois | 1353 |
| New City Vacation Rentals in Chicago, Illinois | 295 |
| Back of the Yards Vacation Rentals in Chicago, Illinois | 277 |
| Brighton Park Vacation Rentals in Chicago, Illinois | 123 |
| Canaryville Vacation Rentals in Chicago, Illinois | 888 |
| Ashburn Vacation Rentals in Chicago, Illinois | 109 |
| West Lawn Vacation Rentals in Chicago, Illinois | 103 |
| Chicago Lawn Vacation Rentals in Chicago, Illinois | 95 |
| McKinley Park Vacation Rentals in Chicago, Illinois | 739 |
| Ducktown Vacation Rentals in Chicago, Illinois | 686 |
| Englewood Vacation Rentals in Chicago, Illinois | 335 |
| Archer Heights Vacation Rentals in Chicago, Illinois | 109 |
| Gage Park Vacation Rentals in Chicago, Illinois | 88 |
| Clearing Vacation Rentals in Chicago, Illinois | 126 |
