Roseland holiday rentals, IL, USA: holiday houses & more

Scroll through and select from holiday rentals in Roseland to find one that's perfect for your trip. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include cable TV and a washer and dryer. You're sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Find the best place to stay - Roseland

51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi

Sleeps 4 · 1 bedroom · 1 bathroom

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Sleeps 20 · 5 bedrooms · 2+ bathrooms

Find spaces that suit your style

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to rent a holiday rental in Roseland?

Length of stay, property type and season are some factors that can influence the price of a holiday home. Simply add your dates of travel to find your dream escape. From comfy cottages to expansive villas, all Vrbo holiday rentals offer incredible value.

How much does it cost to rent a beach house in Roseland?

When you travel and the size and style of the property will help determine the cost of your beachside escape. Enter your Roseland travel dates to view your available options on Vrbo. Did someone just say "private pool"? Use our filters to pick the features and amenities you need.

What are the top attractions for families in Roseland?

Keep the kids amused at these awesome family-friendly attractions in Roseland:

Chicago Museum of Science and Industry
DuSable Museum of African-American History
57th Street Beach

How old do you have to be to rent a holiday rental in Roseland?

You'll need to check with the Roseland holiday property you want on Vrbo as the age limit varies. However, typically it's 16, 18 or 21.

How long can I rent a holiday rental in Roseland for?

The amount of time you can stay in a Roseland holiday rental for differs depending on the property. Simply put in your dates of travel to find available options that offer long-term stays. They include all the things you need to make your extended break more convenient and comfortable, like kitchens and backyards. Some holiday homes may also offer weekly or monthly discounted prices, so you can stay even longer for less.