1263+ Private Villas and Holiday Rentals in West Side |
  1. USA
  2. Illinois
  3. Chicago
  4. West Side

West Side Holiday Rentals

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

Discover more than 1263 vacation rentals available in West 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 West Side.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in West 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 West Side. On average, places to stay near West Side offer 752.47 ft², with nightly prices averaging ZA R6,514.

With Casai, finding and comparing holiday rentals in West 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.

Show more
Show less

Top Accommodation Types in West Side

Type Count
Holiday Apartments 895
Vacation Homes 187
Villas 1

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

Weather in West Side, IL

View the weather forecast for West Side before booking your West 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 West Side, IL

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


Union Station
United Center
University of Illinois Chicago
Douglas Park
UIC Pavilion
Rush University Medical Center
Humboldt Park
Union Park
Garfield Park Conservatory
Chicago Arts District
National Museum of Mexican Art
Garfield Park
Old St Patrick’s Church
Flat Iron Building
Maxwell Street Market
Holy Innocents Church
Addams/Medill Park
Canalport Riverwalk Park
Paseo Boricua
St. Basil Greek Orthodox Church

Other Places to Stay in West Side, IL


Near West Side 331 Properties
West Town 283 Properties
West Loop 198 Properties
East Village 144 Properties
University Village / Little Italy 89 Properties
River West 52 Properties
Lower West Side 45 Properties
Wicker Park 40 Properties
Pulaski Park 30 Properties
Noble Square 30 Properties
Tri-Taylor 27 Properties
Heart of Chicago 27 Properties

Frequently Asked Questions About West Side?

What are the top holiday rentals in West Side?

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

How many holiday rentals have private pools in West Side?

Discover a selection of holiday rentals with private pools near West 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 West Side are best for families?

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

How many Casai.co.za holiday rentals are available in West Side?

As of 2025, Casai boasts over 1263 properties listed in the West Side area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in West Side.

Nearby Neighborhood (16) 
Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1791
Near North Side Vacation Rentals in Chicago, Illinois 818
The Loop Vacation Rentals in Chicago, Illinois 775
River North Vacation Rentals in Chicago, Illinois 484
Near West Side Vacation Rentals in Chicago, Illinois 331
West Town Vacation Rentals in Chicago, Illinois 283
West Loop Vacation Rentals in Chicago, Illinois 198
Lincoln Park Vacation Rentals in Chicago, Illinois 143
University Village / Little Italy Vacation Rentals in Chicago, Illinois 89
Logan Square Vacation Rentals in Chicago, Illinois 78
Wicker Park Vacation Rentals in Chicago, Illinois 40
Bucktown Vacation Rentals in Chicago, Illinois 24
Belmont Cragin Vacation Rentals in Chicago, Illinois 137
Pilsen Vacation Rentals in Chicago, Illinois 3300
Chinatown Vacation Rentals in Chicago, Illinois 3053
Austin Vacation Rentals in Chicago, Illinois 159

People Also Ask

There are 1263 West Side, IL Holiday Rentals

Recently Booked Holiday Rentals in West Side