West Side Holiday Rentals

We compare holiday rentals from owners across Booking.com, Vrbo and Expedia.

Destination
Dates
Guests
Search
  • Up-front pricing
  • No markup
  • Trusted partners

Compare Holiday Rentals, Villas & Resorts in West Side

1,623 villas and rentals
Sort by
See More Properties

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

Discover more than 1623 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 845.95 ft², with nightly prices averaging CA $496.

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.

Other Places to Stay in West Side, IL


Near West Side 317 Properties
West Town 308 Properties
West Loop 186 Properties
East Village 168 Properties
University Village / Little Italy 87 Properties
Lower West Side 56 Properties
River West 46 Properties
West Loop Gate 40 Properties
Heart of Chicago 39 Properties
Pulaski Park 36 Properties
Noble Square 36 Properties
Wicker Park 35 Properties

There are 1623 West Side, IL Vacation Rentals

Recently Booked Hotels, Resorts, or Rentals in West Side

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 Casai.ca holiday rentals are available in West Side?

As of 2026, Casai boasts over 1623 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)

NeighborhoodProperty Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1403
The Loop Vacation Rentals in Chicago, Illinois 632
Near North Side Vacation Rentals in Chicago, Illinois 585
River North Vacation Rentals in Chicago, Illinois 351
Near West Side Vacation Rentals in Chicago, Illinois 317
West Town Vacation Rentals in Chicago, Illinois 308
West Loop Vacation Rentals in Chicago, Illinois 186
Lincoln Park Vacation Rentals in Chicago, Illinois 129
University Village / Little Italy Vacation Rentals in Chicago, Illinois 87
Logan Square Vacation Rentals in Chicago, Illinois 55
Wicker Park Vacation Rentals in Chicago, Illinois 35
Belmont Cragin Vacation Rentals in Chicago, Illinois 31
Austin Vacation Rentals in Chicago, Illinois 24
Bucktown Vacation Rentals in Chicago, Illinois 3138
Little Village Vacation Rentals in Chicago, Illinois 462
North Lawndale Vacation Rentals in Chicago, Illinois 640