479+ Private Villas and Holiday Rentals in Near South Side |
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Near South Side Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Near South Side

Discover more than 479 vacation rentals available in Near South 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 Near South Side.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Near South 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 Near South Side. On average, places to stay near Near South Side offer 927.54 ft², with nightly prices averaging CA $599.

With Casai, finding and comparing holiday rentals in Near South 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 Near South Side

Type Count
Holiday Apartments 409
Vacation Homes 31

Use these Quick Filters to Find a Holiday Rental in Near South 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 Near South Side.

Weather in Near South Side, IL

View the weather forecast for Near South Side before booking your Near South 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

Other Places to Stay in Near South Side, IL


Dearborn Park 3,938 Properties
Field Museum of Natural History 3,763 Properties
John G. Shedd Aquarium 3,734 Properties
Olmec Head No 8 3,727 Properties
National Vietnam Veterans Art Museum 3,553 Properties
Soldier Field 3,548 Properties
Glessner House Museum 3,533 Properties
Copernicus Statue 3,532 Properties
William K Kimball House 3,490 Properties
South Side 361 Properties
South Loop 355 Properties
Prairie District 239 Properties

Frequently Asked Questions About Near South Side?

What are the top holiday rentals in Near South Side?

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

How many holiday rentals have private pools in Near South Side?

Discover a selection of holiday rentals with private pools near Near South Side with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Near South Side are best for families?

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

How many Casai.ca holiday rentals are available in Near South Side?

As of 2025, Casai boasts over 479 properties listed in the Near South Side area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Near South Side.

Nearby Neighborhood (7) 
Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1753
South Loop Vacation Rentals in Chicago, Illinois 355
Prairie District Vacation Rentals in Chicago, Illinois 239
Bronzeville Vacation Rentals in Chicago, Illinois 105
Printers Row Vacation Rentals in Chicago, Illinois 4021
Ickes Praire Homes Vacation Rentals in Chicago, Illinois 2027
Chicago Museum Campus Vacation Rentals in Chicago, Illinois 3407

People Also Ask

There are 479 Near South Side, IL Holiday Rentals

Recently Booked Holiday Rentals in Near South Side