Orland Park Vacation Rentals

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Browse Select Orland Park Vacation Homes

Cozy Midway Home
2.0 star property
9.8 out of 10, Exceptional, (7)
"Love the place. Nice and cozy. Very clean. Beds where very comfy nice memory foam matress and pillows. There was no shampoo,conditioner or body wash in shower but that didnt break me. Brought my own. The parking was good. Nice quiet neighborhood, very close to the highway 55. Super close to midway airport. Like 6 min away. Definitely will stay again. "
Cozy Midway Home
The Best of Wheaton, Family and Pet Friendly
9.8 out of 10, Exceptional, (6)
"The house was perfect for our stay. Located on a quiet street in a great area. Had everything needed and Larry was a great host."
The Best of Wheaton, Family and Pet Friendly
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (114)
"Definitely gently used but was comfortable. Ms. Linnie, the host, is very responsive and accommodating. Was missing hair dryers and flat sheets on beds but did not negatively affect our visit."
Luxury Home Away From Your Home
✽ Charming Cottage ✽ close to College/Town/Station
10.0 out of 10, Exceptional, (34)
"This is an older home that has been renovated into a cute rental. The place was clean when we arrived. The rooms were just as described in the listing. The only bathroom is upstairs. The only concern I had was that the stairs were those older home steep stairs and there were no handrails. We had our older parents with us and them going up and down made me quite nervous. It is near the train tracks, as are many places in Wheaton, so you did hear the trains coming through frequently. "
The price is CA $229
CA $393 total
includes taxes & fees
Oct 8 - Oct 9
✽ Charming Cottage ✽ close to College/Town/Station
Cozy, Beautiful Downtown Unit CHI in Prime River North Location near Mag Mile -
10.0 out of 10, Exceptional, (11)
"The listing did not disappoint for our group of frienda reunighring for a 2 night event. It's just as described & more! Great location, the patio is such a bonus, Dan the host was amazing at communicating before & after, and that patio 😍 Thak you- we hope to he back soon! soon!"
Cozy, Beautiful Downtown Unit CHI in Prime River North Location near Mag Mile -
Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
2.0 star property
9.6 out of 10, Exceptional, (5)
"Place was clean, cozy and in good condition. It was perfect for our 3 day stay!"
Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
Cozy, Beautiful Downtown Unit CHI in Prime River North Location near Mag Mile -
8.8 out of 10, Excellent, (8)
"Great place to stay for a work conference at Sheraton. For three people it was much cheaper than the hotel."
Cozy, Beautiful Downtown Unit CHI in Prime River North Location near Mag Mile -
Furnished Private home in Aurora
9.4 out of 10, Exceptional, (66)
"Very clean, close to the golf course. There were 4 of us. Space worked well for right amount of togetherness and individual time."
Furnished Private home in Aurora
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!
9.6 out of 10, Exceptional, (10)
"We had an awesome stay. Perfect place for a large group where you can chill out together after touring around the city. The neighborhood is quiet. It has 2-carport indoor garage. The property manager responded right away if you have any questions. "
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!
Stunning Condo #2 - Downtown River North!!!
9.4 out of 10, Exceptional, (10)
"Looks just like the pictures, the house was very clean and decorated so cute! The host was very easy to get in touch with if needed. Amazing stay!! "
Stunning Condo #2 - Downtown River North!!!
Home w/ Office + Yard: 25 Mi to Downtown Chicago!
10.0 out of 10, Exceptional, (14)
"I stayed here with my sisters and their husbands while we were in town for our cousins wedding. The place was exactly as advertised and very clean and comfortable. We were able to walk to downtown quickly as well as our aunt and uncles house just on the other side of Lake Ellyn. "
Home w/ Office + Yard: 25 Mi to Downtown Chicago!
Wicker Park Entire House, Private Yard and Parking!
10.0 out of 10, Exceptional, (4)
"The property was clean, spacious and nearby public transportation. Communication was clear and concise. Wicker Park is a great area. Would recommend to anyone trying to visit Chicago with a larger group"
Wicker Park Entire House, Private Yard and Parking!
Clarendon Hills Top Floor
6.0 out of 10, (1)
"The tv in the bedroom was to Old and the batteries in the remote needs to Be replace"
Clarendon Hills Top Floor
Enamored in Elmhurst
2.0 star property
10.0 out of 10, Exceptional, (6)
"The house is lovely and located in a quiet, nice neighborhood. Our host Mark was very accommodating and responsive. When we informed him thatthe pack-and-play and high chair advertised in the listing were not there, he personally went out and bought new ones, and delivered them. We would certainly stay at this property again.he went out"
The price is CA $335
CA $714 total
includes taxes & fees
Sep 29 - Sep 30
Enamored in Elmhurst
Immaculate Brand New Penthouse Chicago!
9.4 out of 10, Exceptional, (9)
"This was such a convenient and overall great stay. There is plenty of room for everyone to sleep comfortably and check in/out was super easy. Definitely recommend this for large groups or families. Would stay here again! "
Immaculate Brand New Penthouse Chicago!
Modern Open Concept Home with Pool Table by Train Station
8.8 out of 10, Excellent, (15)
"Relaxing"
Modern Open Concept Home with Pool Table by Train Station
Welcome to Boss Barbie’s Dreamhouse! Everything is pink.
9.6 out of 10, Exceptional, (5)
"The property was adorable for the girls (age 13). Any questions or concerns were addressed expeditiously. I met the friendly neighbors across the street and next door. The block is quiet, close to the highway and perfect for our visit."
Welcome to Boss Barbie’s Dreamhouse! Everything is pink.
King Bed, DIsney+, Spacious, Family-Friendly House
10.0 out of 10, Exceptional, (17)
"It was clean and nice and quiet"
The price is CA $267
CA $520 total
includes taxes & fees
Oct 21 - Oct 22
King Bed, DIsney+, Spacious, Family-Friendly House
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
9.2 out of 10, Wonderful, (40)
"Excellent property in the heart of downtown. Great place with plenty of room. Very spacious for large family."
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
Luxury Chicago TH is a 10-minute drive to DWTN, perfect for city access RSV Now
9.6 out of 10, Exceptional, (8)
"Stayed at the property for a conference at McCormick. Very convenient and nice."
Luxury Chicago TH is a 10-minute drive to DWTN, perfect for city access RSV Now
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See all available properties in Orland Park
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Orland Park

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (547)
"The property is very nice but self check-in was problematic and parking options are challenging. "
The price is CA $193
CA $266 total
includes taxes & fees
Sep 30 - Oct 1
Sentral Michigan Avenue
Sonder South Wabash
3.5 star property
9.0 out of 10, Wonderful, (374)
"This was my first time booking a Sonder property for my stay and I must say, this may become my preferred option for accommodations. The apartment was clean and safe. Bedding, furniture etc was in excellent condition. I was pleasantly surprised."
The price is CA $260
CA $305 total
includes taxes & fees
Oct 21 - Oct 22
Sonder South Wabash
Sonder Market Hall
3.5 star property
8.6 out of 10, Excellent, (163)
"We were really impressed with the location from the green/ pink line. Shopping was a casual 15-20 minutes walk. 2 pubs across the road. Nice safe environment about the location "
The price is CA $157
CA $184 total
includes taxes & fees
Oct 22 - Oct 23
Sonder Market Hall
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.