Vacation rentals with a patio in Highland Park

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Popular amenities for Highland Park patio rentals

Apartment rentals with a patio

Guest favorite
Apartment in Edgewater
4.94 out of 5 average rating, 69 reviews

Spacious! 3 bedroom apartment in Edgewater!

PatrickRating, 5 stars1 month ago
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.
Guest favorite
Apartment in Hyde Park
4.92 out of 5 average rating, 103 reviews

Spacious 1BR Garden Apt & Parking

TomásRating, 5 stars2 weeks ago
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.
Guest favorite
Apartment in Avondale
4.97 out of 5 average rating, 107 reviews

Lovely 2bedroom 1bath Apt and outdoor seating.

DarenRating, 5 stars1 week ago
A very nice and welcoming place to stay!
Top guest favorite
Apartment in Uptown
4.98 out of 5 average rating, 40 reviews

2 Room Apartment in Vintage Bldg

AudréanneRating, 5 stars2 weeks ago
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.
Superhost
Apartment in Evanston
4.83 out of 5 average rating, 179 reviews

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

SkylarRating, 5 stars1 month ago
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 !
Superhost
Apartment in Glenview
4.86 out of 5 average rating, 28 reviews

1 Bedroom Apartment/free parking

DarrenRating, 5 stars2 months ago
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!
Top guest favorite
Apartment in Palatine
4.96 out of 5 average rating, 166 reviews

Huge Sofa-King Bed-Retro-Private Deck-Downtown Pal

BlakeRating, 5 stars1 week ago
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!
Superhost
Apartment in West Loop
4.9 out of 5 average rating, 49 reviews

Chic 1 BR w Parking

AshleyRating, 5 stars1 month ago
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

Superhost
Home in West Lawn
4.93 out of 5 average rating, 40 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

JoannaRating, 5 stars3 weeks ago
Came for c2e2 with my friends and it was perfect for all of us! Would recommend 💗💗
Top guest favorite
Home in Norwood Park
4.97 out of 5 average rating, 31 reviews

Cheerful two bedroom home with patio/deck

EricRating, 5 stars1 month ago
Beautiful home in a quiet neighborhood with responsive and helpful hosts.
Superhost
Home in Maywood
4.8 out of 5 average rating, 115 reviews

Maywood Relaxation

LewisRating, 5 stars1 month ago
The house was amazing and fancy I really liked it a lot
Superhost
Home in Round Lake Beach
4.89 out of 5 average rating, 202 reviews

Corner Lakefront Property

Donell JordanRating, 5 stars2 weeks ago
Beautiful home just to get away from whatever. Very peaceful and quiet just what we need to hosted a gold birthday
Superhost
Home in Illinois Medical District
4.86 out of 5 average rating, 102 reviews

Casa PLZN Location | Entire Home | Garage Parking

AuraRating, 5 stars2 weeks ago
Happy that this place was available! It was comfortable, clean, and roomy, right in Pilsen. Excellent communication and overall great spot.
Superhost
Home in Irving Park
4.82 out of 5 average rating, 11 reviews

Cozy 4-Bedroom House with Patio

GaryRating, 5 stars5 months ago
One of the best host we have ever stayed with!!
Superhost
Home in Cary
4.83 out of 5 average rating, 93 reviews

Spacious 3 Bedroom

CrystalRating, 5 stars2 days ago
great place to stay, beds were excellent and comfortable. felt just much at home. thanks for a great stay!
Superhost
Home in Bolingbrook
4.92 out of 5 average rating, 130 reviews

The Sunshine Spot

SavahannahRating, 5 stars1 month ago
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

Guest favorite
Condo in Avondale
4.95 out of 5 average rating, 106 reviews

Lovely top floor 2BR/2BA, steps from everything!

CrystalRating, 5 stars2 days ago
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!
Guest favorite
Condo in Bridgeport
4.89 out of 5 average rating, 112 reviews

Convenient & Spacious 3BR Condo w/Free Parking

RachelRating, 5 stars3 weeks ago
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
Guest favorite
Condo in West Town
4.92 out of 5 average rating, 114 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

KristinaRating, 5 stars1 week ago
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!
Guest favorite
Condo in Lincoln Park
4.91 out of 5 average rating, 103 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

DebRating, 5 stars2 days ago
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.
Top guest favorite
Condo in Lake View
4.98 out of 5 average rating, 116 reviews

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

AndrewRating, 5 stars2 weeks ago
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.
Top guest favorite
Condo in Lake Geneva
4.97 out of 5 average rating, 149 reviews

Magnificent waterfront views & cozy fireplace

xueRating, 5 stars1 week ago
"5-star stay! Clean, convenient, and great value. Would book again!"
Superhost
Condo in Near West Side
4.86 out of 5 average rating, 148 reviews

Tri-Taylor/Medical Dist. near West Loop

BibiannaRating, 5 stars2 weeks ago
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.
Guest favorite
Condo in Lake Geneva
4.96 out of 5 average rating, 138 reviews

LakeView-SummerPool-FamilyFriendly-CloseToTown

DaynaRating, 5 stars1 month ago
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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