West Side Luxury Rental
6000 ft²
16 Guests
4 Bedrooms
6 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $3,557/Night
For 7 Nights US $24,902
7000 ft²
32 Guests
9 Bedrooms
7 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $3,156/Night
For 7 Nights US $22,095
2195.84 ft²
12 Guests
5 Bedrooms
2 Bathrooms
Free Cancellation
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Parking
US $2,674/Night
For 7 Nights US $18,721
4004.17 ft²
16 Guests
7 Bedrooms
5 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Parking
- Air Conditioner
US $2,412/Night
For 7 Nights US $16,882
4004.17 ft²
16 Guests
1 Bedroom
4 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- View
- Parking
US $2,234/Night
For 7 Nights US $15,637
2497.23 ft²
21 Guests
7 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- View
- Pet Friendly
US $2,082/Night
For 7 Nights US $14,573
2879 ft²
12 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $2,006/Night
For 7 Nights US $14,045
US $1,996/Night
For 7 Nights US $13,972
21 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $1,986/Night
For 7 Nights US $13,902
4000 ft²
16 Guests
7 Bedrooms
4 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,841/Night
For 7 Nights US $12,888
4000 ft²
16 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Spa
- Fireplace/Heating
US $1,802/Night
For 7 Nights US $12,616
1179 ft²
2 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,802/Night
For 7 Nights US $12,611
Why Choose Rent By Owner for your West Side Luxury Rental?
What makes our Luxury Rental special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for West Side
How to Book Your West Side Luxury Rental
What's our booking process?
Our platform allows you to browse a curated selection of luxury rental. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in West Side
Common Luxury Rental Amenities
What amenities can you expect?
Our Luxury Rental are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in West Side, IL
West Town
Near West Side
West Loop
East Village
University Village / Little Italy
Lower West Side
Wicker Park
Pulaski Park
Noble Square
River West
Heart of Chicago
West Loop Gate
West Side Luxury Rental Frequently Asked Questions
1. What are the top Luxury Rentals in West Side?
There are a lot of options in West Side. If you plan on staying in the West Side area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Luxury Rentals in West Side:
- Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
- NEW LUXURY PENTHOUSE CONDO
- NEW LUXURY CONDO WITH PATIO DECK
- 1F Chicago's Little italy Graystone nearDowntown
- Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
- Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
- Entire Below Level Studio w/Private Sauna
- Private Historic Coach House Wicker Park
- Spacious 3/2 Duplex In Wicker Park Area
2. How many Luxury Rentals are available in West Side?
Currently, the total number of properties listed by RBO in 2026 is over 1534 in the West Side area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Luxury Rentals in West Side.
More Rentals You May Like Near West Side
3500 ft²
18 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $1,703/Night
For 7 Nights US $11,918
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $1,528/Night
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3000 ft²
15 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,469/Night
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5000 ft²
24 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,463/Night
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2400.35 ft²
12 Guests
4 Bedrooms
2 Bathrooms
Free Cancellation
Apartment
- Fireplace/Heating
- Balcony/Terrace
- View
US $1,443/Night
For 7 Nights US $10,103
8 Guests
4 Bedrooms
4 Bathrooms
Pet Friendly
House
- Hot Tub
- Fireplace/Heating
- Pet Friendly
US $1,429/Night
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4000 ft²
15 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $1,419/Night
For 7 Nights US $9,933
3500 ft²
16 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $1,367/Night
For 7 Nights US $9,568
2400 ft²
12 Guests
4 Bedrooms
4 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,353/Night
For 7 Nights US $9,474
3000 ft²
16 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $1,342/Night
For 7 Nights US $9,395
3100 ft²
13 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,322/Night
For 7 Nights US $9,252
1900 ft²
7 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,301/Night
For 7 Nights US $9,108
