Pet-friendly holiday rentals in Oak Park

This wasn’t really supposed to be a “fun” trip. I unfortunately had to put my mom into assisted living, but found this Airbnb close to her home. My 2 boys came with me (10 & 13) and if it wasn’t for the fun accommodations in this house, they wouldn’t have had the awesome time they did. It was a fantastic distraction, and the house felt like a home. We loved the updated bathrooms, the modern look and feel, and don’t forget the basement! We spent lots of time down there playing putt putt and arcade games. My son even hooked up his X-Box and played (which he ended up leaving behind on accident, and the host Marc actually drove it to my moms to drop it off - A SAINT!) We will likely be back at least every couple months to check on my mom and will book here from now on!

We stayed for a week with 2 children of 8 and 10. The place is larger than we expected; which is nice. The street and neighborhood are both really nice. Train is close; which is very handy to visit the city. Close to Lincoln park and many restaurants and shops. This place was very comfortable, private and quiet. Brian was also also very flexible with check in and check out times. Definitely recommended !

Very comfy apartment in a great neighborhood. We were in town for a baseball game and it’s a terrific place for that, just about a 20-minute walk to Wrigley Field. The only thing to be concerned about is the stairs: there are two flights to get into the apartment and they’re fairly steep and small, so if you have mobility issues that would be a concern. I don’t and had no problem. Karen is a lovely host and was very helpful when I was getting into the place and unloading my stuff from my car. There are tons of restaurants and coffee shops in the area, so it’s a great place to explore and hang out.

The home was beautiful. And I love the master bedroom I felt like a queen walking into the room private bathroom. Big backyard. Everything was fabulous and next time I go back I will stay there again if available.

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!

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

Nice place tucked into a quiet, safe neighborhood. Backyard was outstanding. (We wish the weather had cooperated so we could have spent more time outside) One level home with comfy beds and furniture throughout. Kitchen was spacious and clean. Plenty of extra towels and blankets.

Tom's place was really nice and exactly as described. The backyard was perfect for our pup and the neighborhood was really nice to take him on the walk. We would defintely stay there again if we are in the area.

Amazing roof terrace and views! Place is spotless and well equipped. If you’re in town for business or pleasure, this place beats any hotel twice the price!

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

We had a wonderful stay in Chicago with our infant and toddler! The check-in process was smooth and easy, which made settling in stress-free. The apartment was clean and cozy, with fresh sheets, a spotless bathroom and bedroom. The kitchen was fully stocked with all the essential utensils made it convenient to prepare breakfast for the kids. One big plus was the parking, the detailed video provided made it super easy to find the exact location without any confusion. The location of the apartment was fantastic within walking distance to Willis Tower and surrounded by great restaurants. It was also just a short 15 mins drive to major attractions like the Shedd Aquarium, Adler Planetarium, and Navy Pier. Everything we needed was already available in the room, we didn’t have to call out or ask for anything during our stay. Overall, a comfortable and convenient stay for families traveling with little ones. Highly recommended!

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!

The place was spectacular. The views are breathtaking. My family and I loved the place.

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

Great getaway place to stay at. Beautiful patio area as well!

Had a great experience with our stay. The host was very communicative and friendly with their response. The view is impeccable and the location was perfect.

Very clean well appointed space. An older townhome, the unit is fully stocked with everything one would need, and parking behind the unit was extremely convenient. Jay was very responsive and helpful. Close walk to train station and restaurants, on a quiet block, with everything one might need.

Rameez was an amazing host! Making the experience even more enjoyable with his quick responses & fast accommodations. The home is more spacious than it looks in the photos and it truly exceeded my expectations. I had a great stay for my birthday!

Great place in a great location. Would definitely book again!

This is a cozy apartment that is perfect for families, close to a great neighborhood and a nice walk among historic homes to the CTA. Charles was extremely helpful and courteous throughout the entire process. The apartment was very clean and inviting with 3 small but separate bedrooms. I definitely plan to reach out to Charles again next time that I am visiting Chicago with family.

This was a great location for walkable access to downtown Oak Park and the El. Jeff was also an extremely helpful and responsive host! He accommodated an early check-in and was very quick to help us out when we had troubles initially getting into the unit. The space was perfect for our weekend visiting friends in the area!

Place was just as described. Easy instructions to enter and house manual was clear. Steve checked in to ensure all was well upon arrival

David's place was great. It's very spacious, clean and comfortable. It's in a great, quiet neighborhood and walking distance to coffee shops and grocery stores. The backyard deck is also a great addition which we utilized. This was our second time visiting Oak Park and plan on coming back again and would definitely stay here again for sure. David was a great host and was very responsive and detailed with his instructions. I highly recommend this place!!

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.