98+ Private Villas and Holiday Rentals in Southwest Side |
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Southwest Side Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Southwest Side

Discover more than 98 vacation rentals available in Southwest Side. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Southwest Side.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Southwest Side, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Southwest Side. On average, places to stay near Southwest Side offer 382.79 ft², with nightly prices averaging US $203.

With Casai, finding and comparing holiday rentals in Southwest Side is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Southwest Side

Type Count
Holiday Apartments 52
Vacation Homes 35

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

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Southwest Side.

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

Top Attractions Around Southwest Side, IL

Casai offers a large selection of top attractions around Southwest Side . Research things to do on your vacation before you visit Southwest Side.


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

Other Places to Stay in Southwest Side, IL


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 holiday rentals in Southwest Side?

With numerous options available in Southwest Side, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Southwest Side:

Which holiday homes in Southwest Side are best for families?

If you're searching for a family-friendly holiday home in Southwest Side, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Southwest Side:

How many Casai.nz holiday rentals are available in Southwest Side?

As of 2025, Casai boasts over 98 properties listed in the Southwest Side area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Southwest Side.

Nearby Neighborhood (16) 
Neighborhood Property Count
Heart of Chicago Vacation Rentals in Chicago, Illinois 31
Greater Grand Crossing Vacation Rentals in Chicago, Illinois 26
Bridgeport Vacation Rentals in Chicago, Illinois 1353
New City Vacation Rentals in Chicago, Illinois 295
Brighton Park Vacation Rentals in Chicago, Illinois 123
Ashburn Vacation Rentals in Chicago, Illinois 109
Back of the Yards Vacation Rentals in Chicago, Illinois 277
Canaryville Vacation Rentals in Chicago, Illinois 888
Gage Park Vacation Rentals in Chicago, Illinois 88
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
Archer Heights Vacation Rentals in Chicago, Illinois 109
Englewood Vacation Rentals in Chicago, Illinois 335
Clearing Vacation Rentals in Chicago, Illinois 126

People Also Ask

There are 98 Southwest Side, IL Holiday Rentals

Recently Booked Holiday Rentals in Southwest Side