307+ Private Villas and Holiday Rentals in Streeterville |
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Streeterville Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Streeterville

Discover more than 307 vacation rentals available in Streeterville. 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 Streeterville.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Streeterville, 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 Streeterville. On average, places to stay near Streeterville offer 701.86 ft², with nightly prices averaging ZA R5,980.

With Casai, finding and comparing holiday rentals in Streeterville 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 Streeterville

Type Count
Holiday Apartments 159
Vacation Homes 47

Use these Quick Filters to Find a Holiday Rental in Streeterville

★ 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 Streeterville.

Weather in Streeterville, IL

View the weather forecast for Streeterville before booking your Streeterville 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 Streeterville, IL


Loyola University Museum of Art 3,972 Properties
Rush Street 3,953 Properties
City Gallery 3,933 Properties
Fourth Presbyterian Church 3,930 Properties
Chicago Place Mall 3,919 Properties
Museum of Contemporary Art 3,908 Properties
Shops at Northbridge 3,888 Properties
Broadway Playhouse 3,887 Properties
Wrigley Building 3,884 Properties
John Hancock Center 3,878 Properties
McCormick Tribune Freedom Museum 3,865 Properties
McCormick Freedom Project 3,858 Properties

Frequently Asked Questions About Streeterville?

What are the top holiday rentals in Streeterville?

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

How many holiday rentals have private pools in Streeterville?

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

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

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

As of 2026, Casai boasts over 307 properties listed in the Streeterville area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Streeterville.

Nearby Neighborhood (7) 
Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1527
Near North Side Vacation Rentals in Chicago, Illinois 605
River North Vacation Rentals in Chicago, Illinois 317
Rush and Division Vacation Rentals in Chicago, Illinois 88
Gold Coast Vacation Rentals in Chicago, Illinois 37
Near East Side Vacation Rentals in Chicago, Illinois 735
Magnificent Mile Vacation Rentals in Chicago, Illinois 3906

People Also Ask

There are 307 Streeterville, IL Holiday Rentals

Recently Booked Holiday Rentals in Streeterville