Vacation rentals with outdoor seating in Illinois

Host was quick to answer questions and check in was easy. Place was very clean, had a lot of space and well stocked for stay. Was ten minutes from Bald Knob Cross and about 25 minutes from Carbondale. Had breakfast at Iron Whisk in Cobden and was great.

Lovely home with great amenities. Perfect for the family event in Freeport, which was why we were in Freeport. Roger was on top of everything. Would definitely stay here again, as well as recommend to friends.

Tucked along the quiet northern edge of Antioch, this house doesn’t just offer a place to stay - it gives you something to feel. Vaulted ceilings, custom barnwood beds, and raw concrete countertops set the tone: warm, solid, and built with intent. The private beach isn’t flashy - it’s better. Soft sand, still water, and no reason to rush. Grill outside, gather at the big family-style table, then sweat it all out in the sauna that feels like it was made to erase stress. The beds hit the sweet spot between firm and forgiving. Every corner of the place feels curated without being pretentious. Jewel is just up the road if you need supplies, but you’ll quickly forget the outside world exists. And Waylon? The kind of host you rarely get - quick to respond, genuinely helpful, and fully dialed in without hovering. This isn’t just a weekend rental - it’s the kind of place that makes you rethink how you spend your time off. You’ll leave better than you arrived.

Perfect place to stay for my son's graduation from the Navy Academy. Very flexible to the fact we extended our stay to spend more time with our Sailor.. Felt Right At Home!!! Thank you Jacqueline & Mark.. ;-)

Rebecca was a great host! This is an amazing place to stay. It is centrally located in Southern Illinois to all the great hikes. Bell smith springs, garden of gods, trail of tears, crab orchard, fernye cliff, and giant city park. Neighborhood is quiet and the wildlife is abundant to watch in the backyard. Couches and beds were all comfortable. Within 10 minutes of a local gym to exercise if you need. I will say this is a very “nice” Airbnb, not a cookie cutter set up with cheapest things you can find at IKEA. I recommend to book this place, especially long term stays!

Alex is a great host! Dog friendly places are hard to find and his place made my dog feel super comfortable. Love this place and definitely will be back.

We booked this place because it was just a few dollars more than hotels in tue area. What a great call because we had an entire house. This place was perfect for us to come relax with our college son and make him a nice dinner! The house far exceeded our expectations. Everything was perfect! We loved the old feel, with updated touches. Cooked on the grill outside and even had a small fire in the fire pit. Such a peaceful stay! Thank you Jill! You were so quick to respond to any of our messages! We will definitely search for this place in the future!

The River House is a real treat. We loved our stay there and Rhiannon was a very responsive and friendly host. We had everything we needed and being right on the Kankakee River was a bonus. The decor in the house is really cute and stylish. The beds were comfy and the shower was nice and hot with great water pressure. We felt right at home.

The Iklektik House is an absolute gem! Everything we needed for a relaxing and comfortable stay, just enough space for two in a bright, clean, and cozy space with tons of charming little historic details and charm, while still perfectly accomodating for a modern stay. The neighborhood was fantastic with lots to do and see, and we much appreciated the amenities Mindy and Tony offer in their clean and welcoming space (coffee! Plenty of fresh linens and we could have cooked a meal if we had more time) Parking on the street was always easy but we ended up walking a lot since there are so many shops and places to eat in the neighborhood. 11/10 - would absolutely book again!

We loved our stay at Song’s place. The host was very responsive and accomodated all our needs. The moment we entered the house we felt right at home. The place looks even better than the pictures. Extremely clean and organized. Would definitely stay here again.

Good location and had everything we needed. Handy to have nearby stores within walking distance. Great place and would definitely stay again.

Craig was extremely nice and accommodating when it came to my birthday weekend. He responds quickly to all questions asked and makes sure we’re comfortable at all times. This home was clean, accurately described, and had the perfect “home feeling”. Overall, when visiting the area I will be booking here again !

This was a beautiful place with an excellent view of Lake Michigan. Both rooms had comfortable beds and setup with everything you need. Kitchen is well stocked, but we mostly ordered Grub Hub, lol. Loved spending time here and great place to hangout and chat with friends. It is right on the water and we really enjoyed watching the waves crash against the barrier. It is on the 2nd floor, but the stairs are not bad at all. Felt very safe and having the parking space is a great perk. Very commutative and checked in with us to make sure everything was fine. Would definitely stay here again!

This was a beautiful place! it had everything we needed. Oak Park downtown is walkable and has everything you could want. It is an upstairs unit so be prepared for some steps. Parking was easy. Michelle was great! Downtown Chicago is only 15m (if there's no traffic.). We would definitely come back!

Our stay was very nice and comfortable, a nice place to gather and hang out as a group.

Shatrel and Ben were excellent hosts. They gave us clear instructions and were very responsive. The unit is tastefully decorated and clean. The unit is upstairs in a house. The location is about a 40-minute drive northwest from downtown Chicago, so it is convenient to the city while also within walking distance to a train stop with its shops and restaurants. After our experience there, we would stay there again.

Convenient stay right outside of the heart of downtown Chicago! Easy to drive into town for the day. Very comfortable beds and very clean as well. Would recommend

Great place to stay! Quiet neighborhood and walkable distance from a few shops and food places. We enjoyed our stay very much!!

We had a very good stay for a friends wedding a few blocks away in Chicago. As it is very modern, cozy, and clean. Alex's response time is very quick to whatever may arise. We would highly recommend staying there. Thanks for the stay!

John’s place was clean and cozy. The kitchen was immaculate and we appreciated the nespresso machine and pods. The location was excellent, many food and drink choices right outside the door. It was amazing to have our own parking spot! There are a lot of stairs but that is expected in the city. I would definitely recommend this spot to my friends.

What a great experience! If you’re looking to check out a game and be in Wrigleyville this is the place. We had such a blast and the place was exactly like the photos! Josh was always responsive and being able to walk to all the places we wanted to go made it even better! Thank you for your hospitality and making it possible to celebrate my birthday in Chicago!

This is my favorite place to stay in all of Chicago! I try to come up 1-2 times a year and checking to make sure this spot is available is the first thing I do when planning out my trip(s). The apartment is spacious, comfortable, and clean; central to a lot of fun neighborhoods, and right above (and across) from some of the best nightlife in the city. Allan is an awesome host, always available if something’s needed, and super communicative. I’m already looking forward to my next visit so I can stay here again!

Had a great time with friends and we were all able to comfortably hang out in communal spaces, get around the city. The bathroom to room ratio was ideal for a group of girls to get ready and the neighborhood made us feel safe walking around at all times of the day. Would recommend

I highly recommend booking with Ketan! He was so helpful and gave us great recommendations. Check in/out was easy and I will definitely book this place if we have another big group in Chicago!