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Featured Condo Rentals in South Side and around

Overlooking the sandy beach and rocky shoreline, this property offers stunning views of the surrounding lush greenery and distant buildings.

"Everything about the host and stay was amazing this will be my go to spot for my family and me"

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. "

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!"

Compact kitchen with white cabinetry and granite countertop, featuring a stove, microwave, oven, and dishwasher.

"Perfect apartment to go to the convention center, our walk to the event was closer than our friends who stayed in the Marriott and walked via the bridges. "

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."

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. "

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

"super nice place!"

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. "

Enjoy cooking in this well-equipped kitchen with a range hood, double oven, and microwave.

"Unit was very nice and spacious. Communication with owner throughout my stay was excellent. I will definitely consider this unit again my next trip to Chicago."

Kitchen features a central island, stainless steel oven, and microwave, with a framed picture and a vase with flowers.

"Everything was as advertised and super convenient for our group if 8. Highly recommended VRBO! "

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."

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

"Good location and clean property."

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. "

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

"Pics didn’t really line up with the place, but that’s okay. Area was pretty safe, easy to drive around. Hard to get ahold of owners at times, but besides that, it was a good time."

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!"

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

"Very nice amenities. Comfortable beds."

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...