
Vacation rentals with a patio in Highland Park
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Top-rated patio rentals in Highland Park
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Popular amenities for Highland Park patio rentals
Apartment rentals with a patio

Spacious! 3 bedroom apartment in Edgewater!
Awesome apartment in the Loyola Chicago neighborhood. Easy access to the loop with the red line. Host is super responsive. The place was spotless and well stocked when we arrived.

Spacious 1BR Garden Apt & Parking
Mikael's place was amazing. Unlike most places listed around Hydde Park in Chicago, Mikael's place had from great reviews and they were totally right. The place is very well kept, spacious, practical, with very calm surroundings. I had great sleep and having breakfast while looking at the garden was a big plus for me too. I had no issues regarding privacy or noise which is something commonly brought up in listings in this sector, especially in old buildings. Mikael was also very responsive and kind. If I ever go back to Chicago I would definitely consider staying here again.

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

2 Room Apartment in Vintage Bldg
We loved the apartment. It is ideally situated and was perfect for our little dog. The area is really nice an peaceful. It was also easy to get downtown via the red line. Karen was a fantastic host. We appreciated all the little gestures and the fact that she had saved a parking spot for us upon our arrival. We would come back anytime.

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 !

1 Bedroom Apartment/free parking
We stayed at Karolinas apartment for 7 months and she was a wonderful host. She quickly addressed any problems. For example, we locked our keys in the apartment. I texted her and a new set of keys were promptly delivered. The apartment itself is super comfortable. Great furniture and appliances and we enjoyed the outdoor balcony. I would highly recommend renting from Karolina and this apartment specifically. We have no complaints and our stay was wonderful. Thank you Karolina!

Huge Sofa-King Bed-Retro-Private Deck-Downtown Pal
It was a great stay and very close to the train station which was a plus. A good ideal spot if you want to walk downtown to grab a bite. The place is quiet and perfect for a pair, me and my partner really enjoyed the stay. Thank you so much for having us!

Chic 1 BR w Parking
The space looks exactly like the photos, very clean and feels right a home. There’s a little patio in the front as well. I would definitely stay again.
House rentals with a patio

Family Friendly Duplex/9 min from MDW/Free Parking
Came for c2e2 with my friends and it was perfect for all of us! Would recommend 💗💗

Cheerful two bedroom home with patio/deck
Beautiful home in a quiet neighborhood with responsive and helpful hosts.

Maywood Relaxation
The house was amazing and fancy I really liked it a lot

Corner Lakefront Property
Beautiful home just to get away from whatever. Very peaceful and quiet just what we need to hosted a gold birthday

Casa PLZN Location | Entire Home | Garage Parking
Happy that this place was available! It was comfortable, clean, and roomy, right in Pilsen. Excellent communication and overall great spot.

Cozy 4-Bedroom House with Patio
One of the best host we have ever stayed with!!

Spacious 3 Bedroom
great place to stay, beds were excellent and comfortable. felt just much at home. thanks for a great stay!

The Sunshine Spot
We stayed for a week. The house was spacious and clean, and the neighborhood felt very safe. It was close to the mall and any store you'd ever need. Richard was very responsive and helpful! Washer & dryer were great to have for a longer stay. Wifi and smart tv were great. Also was glad there was even a lead in the backyard for our dog!
Condo rentals with a patio

Lovely top floor 2BR/2BA, steps from everything!
Julia was friendly, responsive and accomodating. Her place was beautiful, clean and peaceful. The only gripe is parking but has nothing to do with her. This place is worth it!

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
This was a great place to stay while in town with friends for a weekend! Walkable to great restaurants and shops, and the place was extremely clean and filled with natural light. Comfy beds and good shower pressure. Would stay again!

Renovated 2 Bed Condo Lincoln Park w/ Free Parking
Although I did have the address and some information about the entrance way, the lock box for the keys was a tad difficult to figure out. A call to him and his prompt response helped me out. Talking with him on the phone helped me understand where the free parking spaces were (in a gated area) and how to access them. The smart lock box on the door of the "apartment" was confusing to me but I'm of a different generation. Another call to him, again with a prompt response, helped me out. The only complaints would be that the jet tub in my bathroom wasn't able to be used due to the nozzle not working to fill the tub and there was only one box of facial tissues on the fireplace mantle. For people with allergies, a box in each bathroom would have been a plus. My brother and I enjoyed our stay even though it was a tad noisy due to street noise but ... that's a downtown stay, I suppose.

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!
Under the category of actions speak louder than words, I have stayed at Allan's place about five times, and it remains my first choice when visiting Chicago.

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

Tri-Taylor/Medical Dist. near West Loop
Ariel was helpful when we had questions or encountered issues. The house was in a quiet neighbourhood and a short uber ride away to downtown Chicago.

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!
Quick stats about vacation rentals with a patio in Highland Park
Total rentals
30 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
1.3K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 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
- Six Flags Great America
- 875 North Michigan Avenue
- Geneva National Resort & Club
- The Field Museum
- Lincoln Park Zoo
- Wilmot Mountain Ski Resort
- Flossmoor Golf Club
- Museum of Science and Industry
- Willis Tower
- Lincoln Park
- Wicker Park
- Grand Geneva Resort & Spa
- Alpine Valley Resort
- Chicago History Museum
- Racine North Beach
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