Vacation rentals with outdoor seating in South Side

Caryl was extremely helpful with a check in process and she introduced us the property as well as surrounding local attractions. We felt the place was warm and very spacious for our group and we had a pleasant stay.

Keya was great host and was responsive with any questions we had! Great location and felt secure going in and out of home. Great amenities and was described well! Will definitely consider coming back and would recommend for any people considering. 10 out of 10 for me!!

We enjoyed our 2nd visit as much as the 1st. Great location! Wonderful hosts! Cool house! Comfortable beds! Beautiful serene backyard. (=

Lizbeth’s place was a great stay! It was cozy, clean, and had more than enough space for me and my three friends. While it was a little farther from the city center than I initially expected, the neighborhood made up for it with tons of great restaurants nearby—there was always something good to eat just around the corner. Lizbeth was also a fantastic host—very friendly and super responsive whenever we had questions. Would definitely recommend her place to anyone visiting the area!

Had a lovely stay at Janice's place! It is located a short drive from Logan Square, which has restaurants, bars, and a blue line metro stop. There was also a bus stop just outside the neighborhood. Speaking of the neighborhood, it was very serene and private, with plenty of parking regardless of the time of day. The airbnb is a basement unit, so maybe something to keep in mind if you're on the taller side, but it was spacious, and there was minimal noise from the floor above. Shower had great water pressure! Bedroom was clean and comfortable. Janice was very communicative and clear instructions were given for checkin and checkout processes.

This place was amazing! My friends and I were scared about the parking at first but it was pretty easy. Instructions were really clear and the host was really amazing with their communications. The area that the home was located in felt safe and is pretty quiet. The home itself had great designs and decorations which made the home feel really cozy to me. I would definitely stay here again and I recommend it to others who are traveling to Chicago.

Nyeri was very responsive and helpful throughout our stay and immediately dealt with any issues that came up. Her suggestions were spot on and she even provided a discount code to order food! The space was comfortable for the 5 of us, and allowed us to rest, visit with each other, and prepare meals. There is construction going on next door but we barely heard them. Thanks for a wonderful stay!

Had a great 2 night stay. Everything was clean and exactly as pictures and described. Very cute decor/theme. The layout was great for us, family with older teens. Lots of space and TVs. Great restaurants and some shopping within walking distance. Really good value. Walk to the beach and trails. We were in town for a nearby event and really enjoyed the area this place was in. Host was very responsive and answered questions beforehand. We had no issues with our stay at all and would absolutely recommend.

Adam's place was very clean, comfortable, and well appointed. I appreciated the touches, the abundant parking in front, the proximity to the University of Chicago.

Very quiet neighborhood, the house is an easy 7min walk to the pink line. Quick ride to Chicago downtown. There is a cute bakery within walkable distance as well as a few grocery stores within a mile. The place itself looked exactly like pictures, very clean.

The house is great and very comfy. The host is very communicative and the instructive videos are helpful. However, the neighbors upstairs are really loud, which gets annoying after some time, but I understand that’s not freddy’s fault at all... Overall, it’s a nice place to stay.

Great place! Exactly where we needed to be close to UChicago campus. The home was clean, spacious and comfortable. So many amenities (iron, ironing board, drying rack, washer/ dryer, hair dryer etc) Will definitely book again.

Thank you so much, Matthew! The beds were comfortable, the BNB was extremely clean, but still felt the coziness of Home. The hot tub definitely was the highlight of our wind down at night. We will be booking again!

It was very well maintained, and the apartment felt very peaceful. The area is also very nice, everything you could need is within 10 minutes walking distance.

One of our favorite Airbnbs in Chicago, it has a great central location and great street parking (with a permit). It's cute. clean, and quiet. I highly recommend!

Fantastic location in Chicago! There is great walk-ability to local restaurants, attractions, public transit, etc. It was clean and quiet for our stay. Would book again!

Everything was great! The location was perfect—close to most of the attractions we visited during our stay. We really appreciated how well everything was set up. The honey was a lovely touch, and we especially enjoyed the peaceful, quiet atmosphere away from the city. Thank you for a wonderful experience!

Planned a trip to Chicago for a weekend get away and Michael’s house did not disappoint. Free parking with unlimited parking passes, probably the most friendly/sweet neighbors you’ll find and just a very beautiful home 100% recommend very close to the green line train which we used to get to the loop every day book this house before it’s gone!

Our stay in Evanston was great! The apartment is close to all of downtown Evanston, the Metra, and the L. Also easy access to NU. Everything was just as it says and the free underground parking is a HUGE plus!

Place was great. Clean and well laid out with plenty of room. Enjoyed our stay. Location was further than we thought from our places we planned to visit. They were cutting down and grinding a tree first thing Saturday morning. Convenient cafe right around corner had good breakfast food and coffee. Ubers were fast getting us and to where we needed to go. Parked car and left all weekend. Neighborhood was a little rough with homeless and panhandlers but they left us alone. Great walks to Soldier field and Northern Island. Alex provided all the amenities you need plus some Heinkens to cool us down. We had no issues so we did not need to contact Alex at all but yoyu got to remember the location is on 17 Place not Street so we almost walked into the wrong house and when the dog started barking at us we knew something was up. LOL!!!

This is our 3rd time staying at Thomas and Cynthia place. We would have it no other way. Home away from home every single time.

We had a fantastic stay at this Airbnb during our Chicago trip! The location was perfect — close to everything we wanted to see and do with our kids. The apartment was clean, well-equipped, and exactly as described. It felt like a home away from home. Check-in was smooth, and the host was responsive and helpful throughout our stay. Highly recommend for families or anyone visiting the city!

We had a great stay for an extended wedding weekend with our entire family. Adrian's home was clean, modern, and well appointed. The beds were all very comfortable and linens were very soft. We felt very safe and the garage parking spot was a nice addition. I would highly recommend his home and would not hesitate to rebook there in the future.

We enjoyed our time at this apartment! Nestled in the Bucktown neighborhood of the city, which is peaceful and surrounded by beautiful homes. Nearby Wicker Park and Logan Square have a lot to offer, as well as Lincoln Park (the neighborhood) not being too far away either. While the bedroom and bathroom are on the smaller side, that’s just city life and it is a perfect retreat for 1-2 people. It’s very stylish yet cozy with the decor and all updated appliances and bathroom. I would take note of the stairs for this unit in particular, as it’s on the second level but they were fine and the patio deck was nice! We really appreciated Lauren being accommodating to our late booking. We would definitely stay here again!