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Featured Condo Rentals in South Side

Relax in this stylish living room with a sofa, coffee table, and dining area, perfect for unwinding.

"The house was absolutely beautiful ! Very spacious and nice! Comfy beds and clean. "

Modern kitchen with oven, microwave, and dishwasher, featuring a large window and ample counter space.

"super nice place!"

Classic residential building with a brick and stone facade, featuring a prominent entrance and large windows.

"We enjoyed our stay, and the condo was perfect for my daughter and me. Great location, prompt responses to all communication with owner, super clean and very comfy beds! Main building corridor could use some sprucing up, but nothing major. Overall, very satisfied! Thanks, Khoy!"

Enter a stylish space with a staircase leading to an upper floor, flanked by potted plants and a cozy bench.

"Great location, very clean place. Ample street parking and the owner is very nice. I’ll definitely be booking this location again."

Fridge, microwave, oven, coffee/tea maker

"There was confusion with VRBO regarding our arrival date, no fault of the property owner. They made arrangements to clean the unit and provide lunch for our group while we waited and offered a second night free for the inconvenience. Highly recommend. Property owner went above and beyond!"

includes taxes & fees

10 Aug - 11 Aug

Relax in this inviting living space with a large TV, comfortable sofa, and cozy reading nook.

"Clean, comfortable, and quiet! We enjoyed the condo very much. "

Enjoy a well-equipped kitchen with a refrigerator, sink, and stove, offering a view of the surrounding buildings.

"Two women colleagues. We each had our own bathroom, plus kitchenette for far less money than a hotel room. Clean and close to McCormick Place."

Enjoy cooking in this well-equipped kitchen with an oven, sink, and refrigerator.

"Good location and clean property."

Enjoy cooking in this kitchen with a stainless steel sink, black stove, and white refrigerator, all set against a spacious granite countertop.

"This was a great place for us to stay while members of our family were at the convention. Cheaper than a hotel room, more privacy and more amenities. "

Enjoy cooking in this well-equipped kitchen with a wooden table, refrigerator, and modern cabinetry.

"We enjoyed the apartment. It was clean, had enough bath towels and soaps . The beds were comfortable and the bed linens were comfortable. Each bedroom having their own bathroom was a real bonus. the CTA stop was a fairly short walk. Their we re a lot of places to eat that were within walking distance., The kitchen needed more supplies such as dish towels, mixing bowl and spatula. Enjoyed the stay, would stay again if the need arises."

Classic architecture meets elegant design in this beautifully maintained building with a central entrance and manicured lawn.

"Our family stay was wonderful! The property was great, the owners were available and courteous. "

Features a clean and contemporary kitchen with white cabinetry, stainless steel appliances, and a wood floor.

"Very nice apartment. Great layout. Big bedrooms. Our host was very helpful and always answered our questions within minutes of a text. We also didnt have any problems parking the whole weekend. "

Stunning hallway with a rustic brick wall, patterned rug, and geometric pendant light.

"Very nice amenities. Comfortable beds."

Enjoy cooking in this well-appointed kitchen with a gas stove, refrigerator, and dishwasher.

"Rough start getting into the place but once we got over anything we needed i would use this place again"

Guests can enjoy the deck with a potted plant and a view of the surrounding area.

"The address of this listing is just plain wrong. The host was very helpful, guiding us to the correct address via telephone.The listing states that there’s a code to the lockbox the keys will be in, and that guests will have that code 48 hours before arrival. Neither of these is true.I’ve been using Vrbo since it was HomeAway, and I’ve never been disappointed. The apartment itself was fine—probably the best-equipped kitchen I’ve seen in a Vrbo—but the house rules are absurd in a couple of...

Kitchen features a stove, sink, and microwave, with ample cabinetry and a small window.

Kitchen features a range, microwave, and granite countertop.

"Our group of 16 people really enjoyed staying at this property. We were so close to everything, surrounded by great food amd shopping, we felt very safe, and the property manager was so responsive to us! We would recommended this property to any family or big group and will be staying here if we come back to Chicago!"