
Vacation rentals in South Side
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in South Side
Guests agree: these stays are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 3 pages
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for South Side vacation rentals
Other great vacation rentals in South Side
Superhost

Home in Chicago
4.92 out of 5 average rating, 38 reviewsFamily Friendly Duplex/9 min from MDW/Free Parking
AshleyRating, 5 stars1 month ago
Johanna made us feel warm and welcome. All amenities are included and work well. Excellent shower. She was very responsive and attentive.
Guest favorite

Home in Chicago
5 out of 5 average rating, 5 reviewsBirthday?Anniversary?Showers?3500 sq ft, sleeps 16
ArissRating, 5 stars1 week ago
Vince’s place was amazing, it was such a good location, easy to drive to anywhere in Chicago. Vince was very easy to contact and was responsive within minutes. He made our stay very comfortable. The house was amazing and there was a lot of space, and there was a lot of amenities available for use, for example kitchen utensils and shower amenities. Overall this stay was amazing and I would book this again if I came back in the future
Guest favorite

Apartment in Chicago
4.86 out of 5 average rating, 42 reviewsElegant 4Bedroom with Free Parking in Albany Park
MatthewRating, 5 stars2 months ago
Wonderful stay as always, thank you so much!
Superhost

Apartment in Chicago
4.63 out of 5 average rating, 24 reviewsCity Gem: Stylish 3BR for Urban Explorers
AnnikaRating, 5 stars3 weeks ago
Peaceful, felt like home, very spacious and comfortable
Superhost

Condo in Chicago
4.79 out of 5 average rating, 29 reviewsSpacious condo with open floor plan and fireplace
TatianaRating, 5 stars3 months ago
This place was spacious and perfect for our family (two kids and a baby), with plenty of room for everyone to spread out. The hosts were fantastic! They encountered an issue with the fridge not working just before our arrival but handled it professionally, providing excellent support until it was fixed. We really appreciated their responsiveness and care. We highly recommend this space for families and large groups. One small suggestion: if you’re a light sleeper or have kids, consider bringing a noise machine, as some sound from the upstairs neighbors can be heard. However, this wasn’t a problem for us and is to be expected when staying in a condo.
Top guest favorite

Home in Lombard
5 out of 5 average rating, 25 reviewsSpacious Home in Chicago Suburbs
JenniferRating, 5 stars1 week ago
It was great! The house was lovely and looked newly renovated. It was much roomier than I expected. The beds were very comfortable.
Superhost

Apartment in Merrillville
4.83 out of 5 average rating, 88 reviewsLovely 2 Bed Room Apartment, all to yourself
BiancaRating, 5 stars2 weeks ago
the apartment was extremely cozy and we loved it it had everything we needed and cornelius has been an incredible host always ready to answer our questions
Top guest favorite

Home in Chicago
5 out of 5 average rating, 20 reviewsComfy Home Away From Home
ZakiRating, 5 stars1 week ago
This home completely transformed our view of Chicago. We arrived a little nervous, but the moment we walked in, we were greeted by a space that was warm, welcoming, and absolutely stunning. Every detail was thoughtfully curated, from the sleek kitchen to the plush pillows on the sectional. The kitchen is modern and fully stocked, perfect for cooking and gathering. The living room is beautifully styled and cozy, and the bedrooms felt like luxurious retreats with spa-like linens and calming decor. The basement lounge was a standout with its oversized sectional and elegant bar area, so perfect for relaxing after a long day. We especially loved the little reading nook with the blue chairs. Every corner of this home radiates peace and intentionality. It truly felt like a sanctuary. We left feeling inspired, rested, and already planning our return.
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- West Side Vacation rentals
- North Side Vacation rentals
- South Bend Vacation rentals
- Lake Michigan Beach Vacation rentals
- South Haven Vacation rentals
- Evanston Vacation rentals
- Saugatuck Vacation rentals
- Michigan City Vacation rentals
- Chicago Vacation rentals
- Condo rentals South Side
- Rentals with a hot tub South Side
- House rentals South Side
- Rentals with lake access South Side
- Rentals with breakfast South Side
- Waterfront rentals South Side
- Kid-friendly rentals South Side
- Rentals with outdoor seating South Side
- Pet-friendly rentals South Side
- Rentals with an EV charger South Side
- Rentals with pools South Side
- Apartment rentals South Side
- Rentals with beach access South Side
- Private suite rentals South Side
- Smoking-friendly rentals South Side
- Family-friendly rentals South Side
- Rentals with a washer and dryer South Side
- Bed and breakfasts South Side
- Fitness-friendly rentals South Side
- Rentals with a patio South Side
- Rentals with a fire pit South Side
- Rentals with a fireplace South Side
- Townhouse rentals South Side
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Humboldt Park
- Six Flags Great America
- Museum of Science and Industry
- Chicago History Museum
- Lincoln Park Zoo
- The Field Museum
- 875 North Michigan Avenue
- Wicker Park
- Willis Tower
- Skokie Country Club
- Garfield Park Conservatory
- Lincoln Park
- Chicago Cultural Center
- Promontory Point
- Odyssey Fun World
- Flossmoor Golf Club
- Moraine Hills State Park
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes