South Loop vacation rentals

We found 415 vacation rentals — enter your dates for availability

Discover a selection of 271 apartments, 19 condos, and other vacation rentals in South Loop that are perfect for your trip. Whether you’re staying in a vacation home with your kids and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include a pool and a washer and dryer. Whatever you're looking for, you'll be sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

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, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of vacation rental accommodation in South Loop?
The most popular types of vacation rentals in South Loop are apartments. After something a little different? Vrbo has plenty of options to match the diverse needs of our guests, so you’ll see properties in lots of shapes and sizes. The ideal fit is ready and waiting for you — book yours today.
How much does it cost to rent a vacation rental in South Loop?
Different factors determine what you’ll pay for your vacation rental in South Loop, such as the type of property, season and length of stay. But, all our vacation homes have something in common — incredible value. Simply enter your travel dates to find your dream escape.
How much does it cost to rent a beach house in South Loop?
The average price for a vacation rental close to the beach in South Loop depends on when you’re traveling and the type and size of property you’re searching for. You can quickly and easily find prices on Vrbo by entering your travel dates. Then use the handy filters to pick the number of bedrooms and amenities that you require, like air conditioning, WiFi and a hot tub.
Are there pet-friendly vacation rentals in South Loop?
Pack up a suitcase for your pooch because South Loop has 148 properties that roll out the welcome mat to pets. Let your four-legged friend join in on the family trip at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates and destination, then check our “Pets allowed” filter box.
Can I rent a house with a pool in South Loop?
Dig out your swimwear and pool noodle, because there are 36 houses with a private pool in South Loop. Settle in at one of these sought-after vacation homes and make every day a pool day. Simply enter your dates into Vrbo, then check the “pool” filter to find the perfect place for a splashing good time!
What are popular rental amenities in South Loop?
Nearby museums, a nearby river and a sauna head the list of most popular rental amenities in South Loop. Whether you plan to travel as a party of one, with your other half or as a family, Vrbo will help you find a vacation home that fits your style with all the features you need.
Are there large group vacation rentals in South Loop?
Pick from two vacation properties in South Loop that can accommodate 10 or more people. Whether you’re organizing a trip with the family or a celebration like a birthday, there’s plenty of room to get your group together under one roof.
Are there vacation rentals in South Loop that welcome kids?
Gather the whole crew for an adventure in South Loop at one of our 148 family-friendly vacation rentals. A lot of these stays feature amenities that are perfect for getaways with the little ones, including laundries, extra bedrooms and swimming pools. Simply click on the “Properties good for families” filter and choose your favorite.
What are the top attractions for families in South Loop?
Keep the kids amused at these fabulous family-friendly attractions in South Loop:

  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium

Are there one-bedroom vacation rentals in South Loop?
You’ll find 57 one-bedroom properties in South Loop to pick from. A one-bedroom vacation rental is a wonderful choice if it’s just two of you or if you’re vacationing solo. Add in more space, privacy and convenience compared to a regular hotel, and you’ve got yourself an unforgettable break.
Can I find two-bedroom vacation rentals in South Loop?
Pick from 46 two-bedroom homes in South Loop. Give the kids the second room or maybe fill it with a couple of your favorite people. There’s a comfy spot for whoever’s fortunate enough to be joining in on the fun.
Are there vacation rentals with WiFi in South Loop?
Whether you want to keep up with world events, check emails or post a pic to social media, there are 42 vacation homes with WiFi in South Loop. Check the “WiFi” box when searching on Vrbo and stay connected on your getaway.
How can I find vacation rentals with air conditioning in South Loop?
South Loop has 143 vacation rentals where you can relax and recharge in air-conditioned comfort. To find a stay on Vrbo that features this amenity, enter your dates of travel and use the filters to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in South Loop?
The minimum age is typically 16, 18 or 21. It can differ across properties on Vrbo, so look at the rules of your chosen South Loop stay before booking your escape.
How long can I rent a vacation rental in South Loop for?
The length of time you can rent a vacation rental in South Loop varies according to the property. Simply enter your preferred dates to see a list of options offering extended stays. With many amenities such as laundries and air conditioning, as well as some offering discounted weekly or monthly prices, you’re sure to find a perfect place to call your home away from home in South Loop.

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