Holiday rentals with outdoor seating in Oak Park

I had an amazing stay at the Spacious Designer’s Oasis, Oak Park, IL! The house was centrally located, making it easy to get around and explore the area. It was impeccably clean, beautifully designed, and had the perfect balance of open space and cozy, modern charm. Every room felt thoughtfully curated and comfortable. A special shoutout to Rameez, our host—he was incredibly responsive, warm, and welcoming from the very start. He made sure we had everything we needed and went above and beyond to ensure our stay was seamless. I’d absolutely stay here again and highly recommend it to anyone looking for a stylish and relaxing place to stay. Thanks again, Rameez!

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

This was a fantastic stay! The space was beautiful, spacious, clean, and well located. Definitely a great option if you're in the area and need a larger space.

Best Airbnb stay we have had to date. Incredibly comfortable, clean and quiet. Wonderful experience!

Even more spacious than in the photos! Well-kept place, with a fully stocked kitchen, projector, BOSE speaker, and great backyard. Double shower in the master bedroom, and strong water pressure. Entry is easy with a code. Finally, the host is VERY accommodating, flexible, and responsive. Recommended!

Was a very nice and relaxing place to stay after spending time in the city! Really close to multiple bus stops which made the public transport really easy to access. The inside was very clean and nice, the bed is extremely comfortable! Would stay again!

Excellent place to stay if you want to be in a “suburban-feel” of the city: you’re in a neighborhood that is steps away from a “main street” walkable area with shops. The two parking spots are very convenient and the main floor is so thoughtfully decorated and furnished. Everything is 5 stars, just want to make a few notes: be wary of the stairs as they can be a little slippery if you don’t have any grippy socks or slippers and there is only one full bathroom so you’ll have to share this with the other guests, also there are blinds but no blackout curtains so you’ll wake up with the sun. The neighbors are very nice, but if the kids are out and about you will hear them clearly. Would 100% book again!

The Maple Place was fantastic! Super comfy and cozy for me and my pup. Really well stocked including snacks and wine. Eddie was an awesome host, quick to respond to a question and provided good suggestions for spots in the area. The neighborhood is AWESOME. Loved walking among the Frank Lloyd Wright houses, and it’s a quick walk to his studio and the Unity Temple if you’re in the mood for a tour. It was also a quick 20 minute drive into the city for a concert at Soldier Field. Highly recommend and would pick this place again if I’m back in Oak Park.

Safe and quiet location with easy access to various business and restaurants in very close proximity! Spacious and bright rooms that can literally sleep 8, making it especially spacious for 4 of us. All amenities listed in the ad are functional and easy to use. Plenty of parking spaces for up to 3 cars, a big plus in the Chicago area. Hosts are fantastic for providing all needed services without interfering privacy! We felt like at home!!! Great organic cup coffee is a huge plus to start the morning with! Extremely kids friendly with so many toys, games, and books offered, together with a fancy bunker bed set! Definitely our first choice whenever we visit Chicago!

Absolutely amazing host. The space has everything you could think of and more, and he’s incredibly responsive/available. Bed is very comfortable and the apartment is easy to find/get in and out of.

We had a wonderful stay. The apartment was just as advertised – clean, quiet, and comfortable. Very nicely decorated. The host provided great communication throughout. Nice location, with easy access to plenty of dining, bars, and shopping. Highly recommend!

We stayed on the third floor of the complex and enjoyed Matthew's attention to detail. He gave a lot of thought to all components of his property.

Margerita and Monique's place was exactly what we needed! In a calm and beautiful location, clean, beautifully furnished, private, and had the most comfortable bed! It was a short walk to the train and easy to get around! There was plenty of parking available! We will definitely reserve again when we visit Chicago in the future. Thank you both for opening your beautiful property to us!

Just wonderful. That was one of the most beautiful accommodations I've ever been to. The apartment is totally lovingly furnished. Everything was super clean and tidy. There are even toothbrushes, toothpaste and a sleeping mask, if you need them. The kitchen is also super equipped with everything you need. The short walk to the metro was also very convenient. We would definitely come back.

The stay was for me and my parents. The location was a bit hard to find at first. But once we found it, it was quiet and peaceful. We felt safe. Im 5'2 and could touch the ceiling so keep that in mind my tall folks. We had no issues with it. The parking spot was amazing to have! Its located right inside a town with Walmart, grocery stores & restaurants. It is about 30 mins from downtown. And takes about an hr to get back during the evening hrs. But we didn't mind.

Exactly as described, just what I was looking for. Convenience of proximity to the Blue Line made it very easy for me to check off all the things I wanted to do during my stay. Thanks so much.

It was a very cozy apartment with a nice set up. Easy access to university of Chicago and the lakefront trail. We really enjoyed our stay!

It was a very nice stay! We loved Chicago

We enjoyed a week of comfortable stay at Matt’s place! We were a family of 5 people and had enough space for everyone! We came for my daughter’s wedding and it was great to have lots of things/amenities that helped us prepare for the wedding! Garage spot was helpful! Backyard peaceful and we spent some time relaxing on the deck! Adorable cozy duplex with everything you need for the relaxed and comfortable stay! Matt was respectful, helpful and very responsive! Area is great as well! Thank you so much!!

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.

Great place to stay close to train line. Helpful friendly host He even supplied snacks and water which was very thoughtful. Nice place as described.

Cody’s place was a perfect hideaway from which to venture into the city, and both far enough away to be peaceful but close enough to a string of good restaurants and cafes to be walkable. Check-in and house instructions were comprehensive, Cody himself was proactive and communicative, and the hot tub was a major plus on cool nights. Looking forward to another stay!