Waterfront holiday rentals in South Side

Amy is an excellent host! She was so proactive about reaching out ahead of time and checking in on us. The unit was extremely clean! Easiest check in I have had with Airbnb—clear/specific directions. Amy was also super accommodating with our checkout time—we had a late flight (7:45pm) and we were able to check out at 5pm instead of noon which allowed us to maximize the last day of our trip! SO close to Loyola beach and has easy access to public transit. There are just a few improvements that would make this a perfect Airbnb: 1) the mattress is uncomfortable (extremely firm), 2) there is a beautiful kitchen but it is not well stocked with the basics (strainer, cooking utensils, pots, etc)—we made do by getting a little creative! Not a problem if you plan on eating out the whole time. 3) A few end tables would be nice for setting a glass of water/coffee etc, 4) needs a few more towels for being so close to the beach! Nonetheless, I would love to stay again and highly recommend!!

I absolutely loved my stay at the wine down! The place was decorated beautifully and was equipped with everything I needed. James even went out of his way to give me a couple of courtesy calls during my stay just to make sure everything was going smoothly. I would definitely stay here again in the near future. Thank you for a great experience.

Very cute apartment, on a quiet street. Great distance to Soldier Field. We were able to Uber back and forth to things we wanted to do.

Great place to stay! Can get anywhere in the city, its right off the "L". Not far from Michigan Ave, either. Would highly recommend this place to anyone who is traveling to Chicago.

The apartment was extremely clean!!! I loved the attention to detail. Very quiet street for sleeping at night and easily walkable to beach, restaurants, and attractions.

Great 1st floor town home on the boarder between Rogers Park and Evanston, right on the waters of Lake Michigan. Lots of sunlight (and able to watch the sunrise over Lake Michigan in the morning) and a couple of parks next door. The bathrooms (especially the showers) were great--full size, nice water pressure. I was able to work remotely while I was there without any issues. As others have noted, parking is on the street; but if you're proactive or book with Spot Hero or similar, it's very manageable. I really enjoyed my stay!

I loved this stay. The hosts were very responsive and friendly. The beach being nearby was so nice. We took nightly walks to the beach and it was very peaceful and beautiful. The apartment is spacious, cozy, has bright natural lighting during the day, and has all the amenities you’ll need. It felt luxurious and very homey. The bed was very comfortable and had a goose down blanket. It felt like I was sleeping on a marshmallow or a cloud! Only thing is parking can get a little complicated if you’re leaving and coming back often, but for the most part it was okay. Overall, I would stay here again and recommend this to anyone wanting to book!

Loved my stay! There was a little bit of confusion when it came to checking in and they responded to me almost immediately—which I was so grateful for after a long day of traveling. The amenities were great (me and that Keurig got along like a house on fire) and the apartment was, as described, cozy. It was perfect for me as someone who was traveling solo. After I checked out, they saw that I’d accidentally left my glasses behind and reached out to me to make sure I could grab them. Just a stellar experience from start to finish. Will definitely try to stay here again if the opportunity arises!

The highlight of this place is the location. It’s on a beautiful street in a fun, safe neighbourhood. The place is exactly as Gary describes and matches the pictures well. Gary himself was very friendly and accommodating of my early check in. I would definitely stay here again. Just note that the lockbox with the key can be a bit jammed, it was hard to get it open at first.

Rasheed was very attentive. His home is in an excellent location, walking distance to resturants and shopping. The rooftop provided a spectular view of the city. I would definitely recommend Rasheed's home on a trip to Chicago!

Great stay for me and my friends. Very spacious and beautiful outside space. Plenty of beds and top of the notch kitchen.

Beautiful home layout and very spacious! Location was a quick drive to the city, which was convenient. Host was also very kind and attentive. Thank you Ms. Lilly for our stay!

Hugo was a great host. The house was just like the listing, ideal for a weekend with friends. We were five couples with children, an ideal family atmosphere. It has games and equipment to enjoy the lake and garden, such as a small pool, life jackets, sport balls... It was a great weekend thanks to the space and the house, highly recommended!

Beca is responsive, friendly and helpful. The house was spotless, immaculate really! I'm somewhat of a clean freak - so the bar for cleanliness was right up to my expectations. The decor and plants are much to my liking, so of course I felt at home - away from home. My family and I found it to be comfortable and cozy. I also want to mention that I had a couple of requests and Beca was accomodating, which was appreciated. My husband and I thank you Beca and we surely hope to stay again!

This place was amazing... They layout was terrific. quiet neighborhood, safe, and had everything we needed. we were celebrating my birthday (pre) My friends 🧡 Even set up a Bday table for me down stairs and we had our in vip golden girlz(ladies) celebrations 🍾 😀 😄 ❤️

Stay went very smoothly and I would recommend for anyone seeing an event at Allstate arena(walking distance) or needing a place to stay flying thru O'Hare. Target and a wide variety of fast casual dining 1 min away. The listing mentioned a grill and that was unavailable, you may want to check with the host in advance if you are planning to use any amenities.

The Airbnb was clean, exactly as described, and in a great location. Check in was easy and we were able to get settled right away. William was very proactive in communicating instructions well before our arrival. Overall, we had a lovely time visiting Chicago and would recommend staying here!

everything was extremely nice, unfortunately the knob to change from shower to faucet was detached so we could not utilize the very large beautiful bathtub. The front porch light also needs to be replaced, we opted to leave the front door open to be able to see outside after dark. Other than that everything was extremely nice. Still worthy of a five-star review.

WWWWOOOWWW!! This host team was EXCEPTIONAL! I’ve stayed in plenty of AirBnBs, and I’ve NEVER encountered a host that was so EXTREMELY accommodating, responsive, and kind! Other hosts should take a page out of their book! The only thing I would change, and it’s not a bad thing (just a matter of preference); I would have some type of blinds or drapes over the living room windows. This will allow for privacy when you’re sitting in the living/dining room areas at night with the lights on inside. Hands down, we would without a doubt book with this team again! Thank you Wendy, Matt, and your co-hosts for helping to make our time in Chicago wonderful!

Spacious with many amenities! Great place to relax with friends.

This was truly one of the best Airbnb experiences I’ve ever had. From the moment I arrived, everything felt warm, welcoming, and thoughtfully prepared. The space was not only beautiful and impeccably clean, but it also had so many special touches that made it feel like a true home away from home. What made this stay exceptional, though, was the host. They were incredibly kind, attentive, and genuinely cared about making my visit as perfect as possible. Every question I had was answered so promptly, and they offered wonderful local recommendations that made my trip even more memorable. It’s rare to find someone who goes above and beyond with such sincerity, but that’s exactly what this host did. I left feeling not just like a guest, but like a friend. I am so grateful for this experience and would return in a heartbeat. Highly, highly recommended to anyone considering this stay — you will be in the very best hands!

This place is near so many spots it was awesome! to go down and get food right below or just walking across the street and grabbing some food. the place was very well cleaned, had great spots just to sit and chill. beds very comfortable, rooms very spacious. water pressure can be very in and out sometimes but water was warm/hot and lasted a full shower.

Richard was a great host and very responsive! The air bnb looked exactly like the photos, very beautiful home.

Loved the look of the place and the decor. The wallpaper and artwork were so cool. The space has been updated nicely. I would definitely recommend this location to a friend staying near the city. Instructions to get in were clear and host communicated promptly. A great place to stay for the weekend!