Southwest Side Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Southwest Side, Illinois, USA

10.0 (20 Reviews)
2 Bedrooms 5 Guests
10.0 (1 Review)
4 Bedrooms 5 Guests
From GB £149 per night
|
8.4 (891 Reviews)
1 Bedroom 2 Guests
10.0 (1 Review)
7 Bedrooms 9 Guests
From GB £104 per night
6.6 (1004 Reviews)
1 Bedroom 2 Guests
10.0 (1 Review)
1 Bedroom 4 Guests
10.0 (1 Review)
5 Bedrooms 7 Guests
From GB £93 per night
5.6 (11 Reviews)
1 Bedroom 2 Guests
9.8 (12 Reviews)
1 Bedroom 5 Guests
9.0 (2 Reviews)
4 Bedrooms 7 Guests
8.6 (20 Reviews)
2 Bedrooms 6 Guests
|
8.9 (13 Reviews)
1 Bedroom 3 Guests
6.0 (2 Reviews)
2 Bedrooms 5 Guests
7.8 (7 Reviews)
7 Bedrooms 11 Guests
From GB £125 per night
New
1 Bedroom 16 Guests
6.0 (1 Review)
5 Bedrooms 5 Guests
From GB £129 per night
New
1 Bedroom 2 Guests
From GB £111 per night
New
1 Bedroom 4 Guests
|
7.7 (522 Reviews)
158 Bedrooms 14 Guests
From GB £74 per night
5.0 (832 Reviews)
57 Bedrooms 18 Guests
From GB £70 per night
8.0 (21 Reviews)
2 Bedrooms 1 Guest
10.0 (2 Reviews)
3 Bedrooms 8 Guests
10.0 (2 Reviews)
3 Bedrooms 8 Guests
9.6 (4 Reviews)
3 Bedrooms 10 Guests
9.4 (14 Reviews)
3 Bedrooms 10 Guests
9.4 (3 Reviews)
5 Bedrooms 12 Guests
9.2 (14 Reviews)
3 Bedrooms 8 Guests
From GB £219 per night
New
4 Bedrooms 10 Guests
From GB £84 per night
4.8 (113 Reviews)
1 Bedroom 2 Guests
8.0 (3 Reviews)
3 Bedrooms 8 Guests
4.3 (7 Reviews)
2 Bedrooms 5 Guests
From GB £111 per night
New
2 Bedrooms 4 Guests
New
2 Bedrooms 5 Guests
New
2 Bedrooms 4 Guests
New
3 Bedrooms 7 Guests
New Warm Bungalow in Chicago
From GB £70 per night
New
3 Bedrooms 2 Guests
5.0 (1 Review)
2 Bedrooms 8 Guests
From GB £128 per night
4.7 (24 Reviews)
2 Bedrooms 4 Guests
From GB £66 per night
3.5 (2 Reviews)
1 Bedroom 1 Guest
New
3 Bedrooms 2 Guests
From GB £219 per night
New
5 Bedrooms 10 Guests
From GB £219 per night
New
4 Bedrooms 10 Guests
From GB £196 per night
New
5 Bedrooms 10 Guests
New
4 Bedrooms 8 Guests

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 GB £154 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.

Frequently Asked Questions About Southwest Side?

What are the top vacation rentals in Southwest Side?

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