Vacation Homes in Roseland, Chicago: House Rentals & More

Scroll through and select from vacation rentals in Roseland to find one that's perfect for your trip. Whether you're staying in a vacation rental with friends, family, or even just your pets, you'll have the amenities you expect and more, which might include a hot tub and a washer and dryer. You'll be sure to find a rental to meet everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

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

Top rated rentals - Roseland

Weekend Trip

Peace of mind
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All the privacy of home
Enjoy full kitchens, laundry, pools, yards and more
More for less
More space, more privacy, more amenities — more value
A place for everyone
We stand for diversity, inclusion and families everywhere.
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Frequently asked questions

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

Length of stay, property type and season are some factors that can influence the price of a vacation home. Simply add your dates of travel to find your dream escape. From comfy cottages to expansive villas, all Vrbo vacation 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 vacation rental in Roseland?

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

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

The amount of time you can stay in a Roseland vacation 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 vacation homes may also offer weekly or monthly discounted prices, so you can stay even longer for less.