South Side holiday rentals

We found 2,386 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024

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, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Explore the lakeside setting in South Side

Come and experience South Side and its museums, architecture and art galleries. Revered for its skyscrapers, aquarium and lake, this city is both cosmopolitan and scenic. Take in top local attractions such as McCormick Place and Lake Michigan. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around South Side

Do you want to find top things to see and do in the city? Venture out of your holiday home and experience everything that South Side has to offer. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Lincoln Park Zoo (8.1 mi / 13 km)
  • Galloping Ghost (12.7 mi / 20.5 km)
  • The Dome at the Parkway Bank Sports Complex (18.3 mi / 29.4 km)
  • Adagio Teas (19.2 mi / 30.9 km)
  • Cog Hill Golf & Country Club (19.9 mi / 32.1 km)
  • Orland Park Sportsplex (20.5 mi / 32.9 km)

Exploring the natural landscape of South Side

Whether you're looking for adventure or just want to appreciate the scenery, South Side is a great spot to appreciate mother nature. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Grant Park (4.7 mi / 7.6 km)
  • Millennium Park (5.4 mi / 8.7 km)
  • Jackson Park (2.4 mi / 3.9 km)
  • Lakefront Trail (2.6 mi / 4.2 km)
  • Maggie Daley Park (5.4 mi / 8.7 km)
  • Ohio Street Beach (6.1 mi / 9.8 km)

Travelling to and around South Side

The nearest airport is in Chicago Midway Airport (MDW), located 6.9 mi (11.1 km) from the city centre.

If you prefer to travel by train, Chicago 47th Street Station (Kenwood), Chicago 51st-53rd Street Station (Hyde Park) and Chicago 55th-56th-57th Street Station are the main stations in the city. You can get around South Side by jumping on the metro at 51st Station, 47th Station (Green Line) or Garfield Station (Green Line).

Frequently asked questions

What is the best area to stay in South Side when booking a holiday home?

Among the more desired neighbourhoods to find a South Side holiday home is Essex. When you book your Vrbo holiday property, you'll have the entire place to yourselves. So you won't have to share it with anybody other than your group.

What is the most popular type of holiday home accommodation in South Side?

Apartments are the most popular kind of holiday home in South Side, according to our data. Even if you have a different idea about what you'd like, Vrbo has holiday homes in a variety of shapes and sizes. Browse our options to find your ideal fit.

How much does it cost to rent a holiday home in South Side?

Several factors affect how much you pay for a holiday home in South Side, including the type of property, length of stay and season. Still, all of our holiday homes have something in common — incredible value. Simply enter your travel dates to find your ideal match.

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

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

What are popular home amenities in South Side?

When it comes to home amenities that people look for in South Side, a microwave oven, a fridge and a dryer are at the top of the list. With Vrbo holiday homes, you'll enjoy choices to fit your taste and style, whether you're taking a trip with relatives, friends or even pets.

Are there large group holiday homes in South Side?

You can pick from 14 holiday properties in South Side that can accommodate 10 or more guests. Whether you're planning a family trip or a special event, there's plenty of room to get your group together under the same roof.

What are the top attractions for families in South Side?

Keep the kids busy at these fun family-friendly attractions in South Side:

  • Jackson Park
  • Guaranteed Rate Field
  • Abbott Park

Can I find two-bedroom holiday homes in South Side?

Select from 26 two-bedroom homes in South Side. Put the kids in the second room or fill it with a couple of your best friends. There's a comfy spot for whoever's lucky enough to be joining in on the fun.

Are there holiday homes with WiFi in South Side?

South Side has 105 holiday homes with WiFi, so you can stay connected during your trip. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming TV shows with the family to catching up on social media, these Vrbo homes will keep you online.

How old do you have to be to rent a holiday home in South Side?

The minimum required age is normally 16, 18 or 21. It can change between properties on Vrbo, so look at the rules of your chosen South Side stay before you book.

How long can I rent a holiday home in South Side for?

The amount of time you can book a South Side holiday home for depends on each property. Simply put in your travel dates to browse available options offering longer term stays. They have all you need to make your extended holiday more enjoyable and convenient, like air conditioning and kitchens. Some properties may also offer weekly or monthly discounted prices, so you can stay even longer for less.

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