Waterfront vacation 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.

Good decent place. Responsive & flexible host. Clean & neat interiors with sufficient utensils to manage basic cooking. Close to UIC, which was our primary requirement. Happy & fully satisfied:)

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.

Clean, comfortable, and beautifully appointed apt. Emily and Roya are helpful and communicative, and all the instructions and photos made things very easy. Would happily stay there again!

Great stay. The property is tucked away and is away from all the city noise. It was very clean and everyone was really impressed. Thank you Sally for a great stay.

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!

We loved this stay!! It’s a beautiful apartment and is walking distance to a great coffee shop called charmers, as well as almost ON Jarvis beach! The hosts are very friendly and preach over communication and make sure that you have all of the information you need! They allowed us very early check-in had we needed it (I believe by 2pm!) and the apartment was spotless! Very comfortable bed and living area, plus an office if you’re visiting for work. This is a great part of Chicago, with most Ubers we took ending up around $20! There is ample street parking on Jarvis, especially with the beach entrance at the end of the street. We would recommend this space and these hosts to anyone and everyone visiting Chicago. They were so kind and organized and really made for a wonderful trip!

Great home and location. Safe neighborhood, walkable to restaurants, shopping, beach. Home was clutter free, clean and well maintained. Beds were comfortable and we had plenty of supplies for duration of stay (fresh towels, blankets, paper products, soap, shampoo, conditioner, etc.) Rooftop deck with nice view. Host was very responsive with any questions and communicated well. House was perfect size for our group of 6. We appreciate Rasheed making our stay perfect! Will stay here again in the future.

Great place to stay! LOVED the lagoon access with kayaks and the walking distance to the beach. Home was stocked with so many necessities and extras (beach wagon, cooking supplies, games, plenty of towels & extra blankets, etc.). Some furniture a bit old and the smaller beds not super comfortable, but overall the value and other amenities well made up for it. Perfect to spend casual time at the lagoon or beach.

Highly recommend this Airbnb. The owner has truly made it a home away from home. She has everything you need in the kitchen, plentiful pillows, extra towels and blankets. The house is very private as it is at the end of a cul de sac in a quaint neighborhood. There is a walking trail and field directly behind the house where you see families and people with their dogs. Though very tranquil, the house is very close to stores and restaurants. It was very clean and rivaled most hotels in that regard. The beds were comfortable and the showers were perfect. Nice that it had two sitting areas and TVs in every room! The most amazing thing about her property is Stephanie herself. She takes great pride and was always readily available. I felt like I had a friend while away from home. She helped with whatever she could.

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 is a great host. There was one small issue through no fault of his own but Hugo quickly took care of it. The house is huge and we thoroughly enjoyed it. It was so much do we were never bored. Just sitting and relaxing on the deck was great the view is amazing. My friends want to book again for our getaways. It was so peaceful. The rooms are great and all spacious. It was 9 of us and we still had extra rooms left. The dining table was big enough for us to eat our meals there together and we loved that. Thank you Hugo we had a great time and took so many pictures.

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 🍾 😀 😄 ❤️

We had a great stay here with family and friends. It was our daughter’s birthday and they surprised her with a birthday gift. The place is beautiful. So many seating options to just hang out and enjoy the lake. Late night fires, games, swimming. It was so fun. Lots of amenities inside. There wasn’t anything better that they could have done to make this weekend even better. Highly recommend.

Came for the BOA Half with my young family. It was a different part of the city than we usually stay, so I was a little nervous but once we arrived I felt very safe - easy access to the lake front trail for a quick run and easy to get to downtown by car. Perfect accommodations!

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!

If you're looking for a place in Chicago that is gorgeous to stay in with easy access to public transit, this is it! The hosts were super helpful with recommendations and quick to answer with any questions. I would definitely stay there again!

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!