
Vacation rentals with outdoor seating in Highland Park
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Top-rated outdoor seating rentals in Highland Park
Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Highland Park outdoor seating rentals
House rentals with outdoor seating

Powers Lakehouse Loft
It was exactly what we were looking for. Very quiet with beautiful views. Being able to sit in the hot tub and take in the sunset was incredible. Any questions we had were answered quickly by this very kind host.

All seasons country house
Agnieszka's place was perfect for our visit with our son as he graduated boot camp. The home had everything we needed. The minimal decorations made it very easy to clean and easy to find all our stuff when we left. The home is beautifully remodeled on the inside. Much respect to the designer. We brought extra toiletries and paper products and dishwasher tabs because we were staying so many days. There was an adequate amount for a simple weekend stay. Plenty of sleeping space for several people. Just remember there is one bathroom. By the way, there is a great Jewel-Osco grocery store close by. We also visited an exceptional museum in Volo. It was perfect for a family, especially the boys! I really enjoyed the short drive to Kenosha, WI to gather stones by Lake Michigan.

Casa PLZN Location | Entire Home | Garage Parking
Great place! I’ll definitely be coming back! The beds are amazing!

Gorgeous and Luxurious 3 BR Home
This is a great house to stay for a family or two couples. Out of several ABNBs, this one gets the award for most clean. There is a fairly new Italian restaurant, Il Girasole Trattoria, that is walk-able and delicious. You will not be disappointed with your stay.

3 x Queen Beds + Pull Out Sofa Bed - No Stairs !
Amazing house and location. Great host. Highly recommend.

Little Blue House
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.

Spacious 3 Bedroom
The home is a great place for a family, we were able to stay a week comfortably with younger kids .

The Country Life! Entire House.
Cathy was a great host, very responsive! House was great, it accommodated our family size perfect. The only thing in my opinion that was missing was washer and dryer access in the home. We were traveling with toddlers and couldn’t wash a load of clothes. But aside from that everything else was great.
Apartment rentals with outdoor seating

iKlektik House Chicago / Robin
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!

Modern 3BR with Private Rooftop & Free Parking
A great place to stay for a family to explore downtown Chicago. The location is convenient, with easy access to major attractions, and restaurants. The home was clean, cozy, and well-equipped — we truly felt like we were at our own home. The host was responsive and thoughtful, which made our stay even more comfortable. Highly recommended!

Lovely 2bedroom 1bath Apt and outdoor seating.
A very nice and welcoming place to stay!

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private
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 !

Executive Apartment on Lake Michigan with parking
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!

Large sunny 3BR apt. in downtown Oak Park
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!

Victorian Home in Old Town
I really enjoyed my stay! I loved the art and decor of the space. I am a solo traveler and I felt safe being here. There are written instructions on the door and in the home that explain almost everything I needed. I felt safe in the neighborhood! I would get back late and felt safe doing so. There are multiple stores within walking distance so it was easy to grab food or any items I may have needed. I didn't have a car and found it very easy to get to everywhere I wanted to go. Shampoo/Conditioner/Body Wash was a pleasant surprise to have! Along with the teas and coffee items. The space was a great size and I had everything I needed. It was easy to come and go and check in was very easy. I would stay here again, Lynn was super responsive, helpful, and kind! The bedroom area doesn't get much light, but it wasn't an issue for me. Bed was comfy, home was beautiful, and I loved my stay. Thank you so much Lynn!

Avondale Cozy 1 Bedroom Attic Apartment 4th FL
Great place, beautiful attic and great amenities from host!
Condo rentals with outdoor seating

Charming, Cozy & Eclectic Condo in Lake Geneva!
Tricia's place was wonderful. It was a close 5 minute drive to William's Bay, where we spent most of our time. The home was perfect, quiet, and we'd love to stay here again!

Convenient & Spacious 3BR Condo w/Free Parking
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

Luxuriously bright 3-bedroom condo: The Treehouse
Great place to stay! Quiet neighborhood and walkable distance from a few shops and food places. We enjoyed our stay very much!!

Magnificent waterfront views & cozy fireplace
"5-star stay! Clean, convenient, and great value. Would book again!"

LakeView-SummerPool-FamilyFriendly-CloseToTown
We loved our stay at this beautiful location. It was close by to everything we wanted to do and the condo was exactly what we were hoping for! Rachel gave great recommendations and was so responsive to our questions. We will definitely stay here again!

Spacious 4 Bedroom Condo
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

Luxurious River North 3BR/2BA- Free Onsite Parking
Neel went above and beyond for my family and I during our stay. The unit was quiet, fun to hang out in, extremely clean, great layout for a family, very convenient parking, and quiet. I would highly recommend staying here! Thank you Neel!

Wicker Park/Bucktown condo with large balcony
Lauren’s condo is nestled in a quiet peaceful neighborhood. It is an ideal location for us just a 12 minute walk from our family’s condo. It is within walking distance to coffee shops, restaurants, and shopping. Lauren was very responsive to any questions. The condo is pleasing and tastefully decorated. Her condo was clean with a comfortable bed and bed linens. We love the neighborhood and look forward to our next visit.
Quick stats about vacation rentals with outdoor seating in Highland Park
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ184 before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- 875 North Michigan Avenue
- Wilmot Mountain Ski Resort
- Six Flags Great America
- The Field Museum
- Lincoln Park Zoo
- Lincoln Park
- Wicker Park
- Museum of Science and Industry
- Geneva National Resort & Club
- Grand Geneva Resort & Spa
- Alpine Valley Resort
- Chicago History Museum
- Willis Tower
- Racine North Beach
- Brookfield Zoo