Southwest Side Villa Rentals

Compare Villas, Resorts, & Rentals in Southwest Side, Illinois, USA

New Midway Paradise with Kids Room
From GB £311 per night
New
4 Bedrooms 8 Guests
10.0 (1 Review)
7 Bedrooms 9 Guests
From GB £124 per night
|
8.4 (869 Reviews)
1 Bedroom 2 Guests
10.0 (14 Reviews)
2 Bedrooms 5 Guests
10.0 (1 Review)
5 Bedrooms 7 Guests
From GB £103 per night
6.6 (1004 Reviews)
1 Bedroom 2 Guests
9.0 (2 Reviews)
4 Bedrooms 7 Guests
From GB £78 per night
5.0 (9 Reviews)
1 Bedroom 2 Guests
10.0 (1 Review)
2 Bedrooms 5 Guests
|
8.9 (13 Reviews)
1 Bedroom 3 Guests
9.8 (12 Reviews)
1 Bedroom 5 Guests
7.9 (6 Reviews)
7 Bedrooms 11 Guests
9.0 (18 Reviews)
2 Bedrooms 6 Guests
6.0 (1 Review)
5 Bedrooms 5 Guests
From GB £124 per night
New
1 Bedroom 16 Guests
|
7.7 (677 Reviews)
158 Bedrooms 14 Guests
From GB £129 per night
New
1 Bedroom 2 Guests
From GB £73 per night
5.0 (832 Reviews)
57 Bedrooms 18 Guests
From GB £110 per night
New
1 Bedroom 4 Guests
From GB £70 per night
8.0 (21 Reviews)
2 Bedrooms 1 Guest
New
2 Bedrooms 4 Guests
10.0 (2 Reviews)
3 Bedrooms 8 Guests
10.0 (2 Reviews)
3 Bedrooms 8 Guests
From GB £147 per night
10.0 (1 Review)
3 Bedrooms 6 Guests
9.6 (4 Reviews)
3 Bedrooms 10 Guests
9.4 (12 Reviews)
3 Bedrooms 9 Guests
9.4 (3 Reviews)
5 Bedrooms 12 Guests
New
2 Bedrooms 4 Guests
From GB £84 per night
4.8 (113 Reviews)
1 Bedroom 2 Guests
8.0 (3 Reviews)
3 Bedrooms 8 Guests
5.0 (1 Review)
2 Bedrooms 8 Guests
From GB £127 per night
4.7 (24 Reviews)
2 Bedrooms 4 Guests
From GB £65 per night
3.5 (2 Reviews)
1 Bedroom 1 Guest
From GB £110 per night
New
2 Bedrooms 4 Guests
New
3 Bedrooms 2 Guests
From GB £218 per night
New
5 Bedrooms 10 Guests
From GB £218 per night
New
4 Bedrooms 10 Guests
From GB £195 per night
New
5 Bedrooms 10 Guests
New
4 Bedrooms 8 Guests
From GB £74 per night
New
1 Bedroom 5 Guests
New
2 Bedrooms 5 Guests
New
2 Bedrooms 5 Guests

About Southwest Side Vacation Rentals

There are more than 87 incredible getaway rentals that are available in Southwest Side. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Southwest Side.

BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Southwest Side, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Southwest Side. Places to stay near Southwest Side are 396.56 ft² on average, with prices averaging GB £156 a night.

BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Southwest Side. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.

Frequently Asked Questions About Southwest Side?

What are the top hotels or resorts in Southwest Side?

How many hotels, resorts, or rentals are available in Southwest Side?

BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2025 is over 87 in the Southwest Side area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Southwest Side. 

Nearby Neighborhood (16)

Neighborhood Property Count
Heart of Chicago Rental Villas and Private Getaways in Chicago, Illinois 27
Greater Grand Crossing Rental Villas and Private Getaways in Chicago, Illinois 471
Bridgeport Rental Villas and Private Getaways in Chicago, Illinois 1353
New City Rental Villas and Private Getaways in Chicago, Illinois 295
Brighton Park Rental Villas and Private Getaways in Chicago, Illinois 123
Back of the Yards Rental Villas and Private Getaways in Chicago, Illinois 277
Ashburn Rental Villas and Private Getaways in Chicago, Illinois 109
Canaryville Rental Villas and Private Getaways in Chicago, Illinois 888
McKinley Park Rental Villas and Private Getaways in Chicago, Illinois 739
Ducktown Rental Villas and Private Getaways in Chicago, Illinois 686
Englewood Rental Villas and Private Getaways in Chicago, Illinois 335
Archer Heights Rental Villas and Private Getaways in Chicago, Illinois 109
West Lawn Rental Villas and Private Getaways in Chicago, Illinois 103
Chicago Lawn Rental Villas and Private Getaways in Chicago, Illinois 95
Gage Park Rental Villas and Private Getaways in Chicago, Illinois 88
Clearing Rental Villas and Private Getaways in Chicago, Illinois 126