Pet-friendly holiday rentals in Woodlawn, Chicago

We enjoyed our stay. Clean, nice house, and in a location convenient to everything we wanted to do. Host was very responsive when we had questions. We loved being so close to the train. Great restaurants around, and also a convenience store and Family Dollar right around the corner for anything you need!

Adam was a great host and very responsive. We loved our stay. The house was clean and the house is easily accessible to everything. Would definitely recommend!

We had an excellent stay here. hosts went above and beyond to make sure we had everything we needed. beautiful house and parking spot was ideal.

I enjoyed staying at Rich's place. If you want to fish, the calumet river Greenway isn't far, and it's easy access to I-57 N/S too.

House is centrally located . Clean. Host was responsive. 100% recommend this property !

We stayed for almost a week with three dogs. Sarah's place was perfect for our needs - great backyard, comfortable beds, clean and equipped kitchen, and awesome location - close to Chicago, Indiana dunes and easy to navigate thru, no traffic. Sarah and her family (and their amazing dog Chandler) are super friendly and helpful. We will definitely stay there again once back in the area.

We had a great stay in Chicago, a lot in part due to the location of this AirBnB. It's only a couple blocks from the Sedgwick metro station, so we were easily able to get there from O'Hare, then getting to the Loop or up to Wrigleyville was very easy. We had one driver in our group and he had no issues with the parking either. The apartment/home itself was as-advertised. While the bedrooms themselves are a little small, the common areas of the apartment are very spacious. The neighborhood itself was nice and peaceful too. This is more of a personal preference, but if you're like me and enjoy high water pressure, just be aware the shower pressure is not very strong. That didn't take away from our experience at all though, would certainly stay again.

My family & I stayed at Vic’s place over the weekend to attend a baseball game and check out Chicago. I’m so happy we chose Vic’s home. It was very clean and in a great location. When heading upstairs to check out the room, I noticed a black, sticky stain on the comforter. I took a picture & sent it to his team . Within minutes he called and had a new blanket delivered as well as ping pong balls! The customer service was no less than excellent. The home was stocked completely. If you are heading to Chicago I suggest booking with Vic!

We had a fantastic stay at this beautiful stay in downtown Chicago. The views were absolutely incredible! The home gave us a breathtaking look at the city skyline, day and night. The location couldn’t have been better, as it was right in the middle of everything, with restaurants, shops, and attractions all within pretty good walking distance. The unit itself was spotless when we arrived and had everything we needed. The bed was super comfortable, and the space felt both modern and welcoming. It was the perfect spot to relax after a day out exploring the city. The host was also very responsive and helpful!! Would definitely recommend this place to anyone looking for a clean, comfortable, and stylish stay in downtown Chicago. We’d happily stay here again!

Nice house with updates. We used all four bedrooms, so everyone had their own space. Kitchen and living room looked nice, but a bit cozy if everyone was in the space at the same time. There was a large breakfast nook/counter in the kitchen instead of a table. More dishes, mugs, etc. in the kitchen would have been nice. The coffee maker and provided K-cups were great! Would definitely stay again if it's available when we are in the area again.

Beautiful apartment in Chicago’s Gold Coast area - lots to do, easy walking distance to shops, restaurants and Oak Street Beach (and a view of the beach from the dining room). Well appointed building with a rooftop pool, gym and lounge. Quiet neighbors on the floor.

Excellent place to stay, easy access to highway, quick ride to downtown

Kevin and Kayla’s unit on W Diversey Ave was a cozy and convenient spot for our Chicago trip. The space was clean, well-equipped, and had everything we needed, with quick access to buses and the Blue Line. The only minor downside was some occasional dog-walking noise from the unit above, but as it has already been mentioned before, it is to be expected. Mattresses were a bit wobbly for our tastes but it's a matter of preference. Overall a great, cozy place on a very convenient location in Chicagoland. What really stood out was Kevin’s excellent hosting—he went out of his way to make us feel at home, regularly checking if we needed anything, and was quick to help in-person when we had a small hiccup on our last day. Super responsive and friendly and a true host!

Great value for a work trip! Easy to find, convenient amenities, and Patty was very proactive with a clear, easy check-in. Would recommend for a small group.

Very comfortable accommodations, Newly renovated and safe on street parking. All in all a great stay for a graduation weekend.

Great beautiful little oasis, a home away from home. Loved the animals for the kids & us they were friendly, came right up to you and kids even got to help feed. Karen did check to see if we needed anything.

My family of 5 including my elderly parents had a lovely stay at Rachel and David’s house for our son’s graduation from UChicago. It is in a quiet location that is very close to the university. The hosts were very friendly and flexible. The place is spacious, light and airy and extremely clean. The beds (especially the two large bedrooms upstairs) had usually comfortable beds. All in all it a 10 out of 10!

This place is definitely a gem! Excellent location and spacious house for a family! We will book here again when visiting the area. Very clean, accommodating and comfortable stay!

I was kind of skeptical about the location at first lol!! Once we got settled in, everything felt good. I found out that the house was only 6 mins away from the church event we were attending. Keya was very attentive and responded in a timely manner. I would love to use her place whenever I'm in Chicago!!

Me my freinds and family enjoyed our stay. The host was very quick to respond to any concerns. The home was clean and spacious. The decor was nice to take pictures. I liked that it had a bathroom downstairs for easy assess. We will come back when we visit Chicago again. Thanks you guy you were awesome.

Loved being just a couple blocks from the Western Pink Line station and bus stops both north-south and east-west.

Terrific apartment, and spotlessly clean. We were only 2 people, but it had a king and a queensize bed in 2 separate bedrooms, as well as a comfortable and well dfurnished iving room. Very modern and up to date.. Kitchen was ample and well equipped and stocked with basic staples. We didn't meet our josts ut they were responsive to our messages.

Quiet and friendly neighborhood. Very walkable. Place had everything I needed for the stay. Will definitely return if I’m ever in the area again.

Host was super responsive and helpful. The place was good, we had no major concerns. We enjoyed our stay!