93+ Rental Villas and Private Getaways in Southwest Side |
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Southwest Side Villa Rentals

About Southwest Side Vacation Rentals

There are more than 93 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 378.6 ft² on average, with prices averaging US $207 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.

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Top Private Villas, Resorts, and Rentals in Southwest Side

Type Count
Holiday Apartments 49
Vacation Homes 33

Use these Quick Filters to Find a Vacation Rental in Southwest Side

★ Pro Tip: BedroomVillas is a luxury vacation rental website, pulling some of the top private villas and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible beach houses and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Southwest Side with BedroomVillas.

Weather in Southwest Side, IL

View the weather forecast for Southwest Side before booking your Southwest Side Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Stay Near Southwest Side's Top Attractions

A Large Selection of Villas and Vacation Rentals from Around the World Southwest Side's Research Top Attractions For Your Vacation


Marquette Park
S.S. Peter and Paul Church
Churches of Ukrainian Village
Balzekas Museum of Lithuanian Culture
Crawford Medical Arts
Holy Cross Hospital
University of Illinois Mile Square Health Center
St. Bernard Hospital
Navy Pier
Wrigley Field
McCormick Place
Millennium Park
Union Station
Soldier Field
Willis Tower
Art Institute of Chicago
United Center
Grant Park
John G. Shedd Aquarium

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Canaryville 888 Properties
McKinley Park 739 Properties
Ducktown 686 Properties
Englewood 335 Properties
New City 295 Properties
Back of the Yards 277 Properties
Brighton Park 123 Properties
Garfield Ridge 123 Properties
Archer Heights 109 Properties
West Lawn 103 Properties
Chicago Lawn 95 Properties
Gage Park 88 Properties

Frequently Asked Questions About Southwest Side?

What are the top hotels or resorts in Southwest Side?

We provide an array of great vacation destinations in Southwest Side. If you are looking to stay in or around the Southwest Side area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Southwest Side:

Which hotel or resort in Southwest Side is best for families?

Searching for a family-friendly getaway in Southwest Side? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

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 93 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
Back of the Yards Rental Villas and Private Getaways in Chicago, Illinois 277
Brighton Park Rental Villas and Private Getaways in Chicago, Illinois 123
Ashburn Rental Villas and Private Getaways in Chicago, Illinois 109
Canaryville Rental Villas and Private Getaways in Chicago, Illinois 888
West Lawn Rental Villas and Private Getaways in Chicago, Illinois 103
Chicago Lawn Rental Villas and Private Getaways in Chicago, Illinois 95
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
Gage Park Rental Villas and Private Getaways in Chicago, Illinois 88
Clearing Rental Villas and Private Getaways in Chicago, Illinois 126

People Also Ask

There are 6 hotels in Southwest Side and 82 rentals

Recently Booked Hotels, Resorts, or Rentals in Southwest Side