Orland Park Vacation Rentals

Browse Select Orland Park Vacation Homes

Furnished Private home in Aurora sleeps 9 guests

9.4 out of 10, Exceptional, (73)
"Our party came to town to visit relatives during Christmas holidays. The house was in good working order and met our needs. Beds were comfortable with easy check- in/ check- out."
Furnished Private home in Aurora sleeps 9 guests

Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow

10.0 out of 10, Exceptional, (6)
"Stayed here with six others for a girls trip.The house was beautifully decorated, beds were comfy, and the backyard was such a nice spot to hang out in during our downtime. We loved how much space we had and the attention to the vibes. Adam was super helpful and responsive before and during our stay. We all wished our trip was longer!"
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow

Spacious 5-bedroom house with movie room, game room and more!

10.0 out of 10, Exceptional, (2)
"This was a great rental experience from start to finish. Everyone was impressed with the space, and the location couldn't be better. We will definitely be back. "
Spacious 5-bedroom house with movie room, game room and more!

Woodlawn Oasis...10 Minutes to Dining & Downtown

9.6 out of 10, Exceptional, (10)
"The property has lots of space and a game room, ideal for a fun getaway with a large group. Close to bus stops and Metra station (different from metro station, we learned this the hard way). Walking distance from the U of Chicago."
Woodlawn Oasis...10 Minutes to Dining & Downtown

LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

10.0 out of 10, Exceptional, (2)
"The property was very nice and spacious. The location was great and the parking in the back was amazing. We felt safe and happy our whole stay. "
LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

LakeHouse

10.0 out of 10, Exceptional, (13)
"Overall great experience! Great home, I love the decor of the entire home. And I will definitely recommend to others and will book again "
LakeHouse

Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

9.2 out of 10, Wonderful, (7)
"The house was good, plenty of space. The steps were hard to get up and down but the upstairs was a nice space. House had a bit of a musty odor and the windows could use a cleaning. One night while watching a movie, we received a text stating we were had a loud party and to keep it down. They must have big brother watching us as the only party going on that night was in the movie. Overall the house was close to the city but in a nice Neiborhood. Having a fenced yard with off street parking...
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

Discover Wheaton's charm.

9.8 out of 10, Exceptional, (9)
"Larry's property.... I can't even call it a property. It's a HOME!!!! As soon as we walked in, it felt like we were coming to a loved one's house. It was so perfect!!!! We traveled FAR to get there, with our two little girls and our dogs. We were exhausted and overwhelmed after the drive and the Thanksgiving holiday chaos. But walking in, we were immediately so comfortable and cozy. He had towels and cloths set up on the dressers in every room (something I do for my own guests in our own home!)...
Discover Wheaton's charm.

Spanish style home with in-ground pool

9.8 out of 10, Exceptional, (37)
"We really enjoyed the stay! The owner is super responsive and went above and beyond for anything we needed and didn’t have while there. If you will be there for a specific event such as hosting a holiday, make sure to confirm that appliances are available that you might need beforehand. They will make sure you have them! You may want to also bring extra paper towels and toilet paper and toiletries. The TVs are great, and there’s room to get work done. We had a great time here and would...
Spanish style home with in-ground pool

King Bed/Fast Wi-Fi/Spacious/Family-Friendly/Just 2 steps to enter House

10.0 out of 10, Exceptional, (22)
"I really enjoyed our stay at this location. It had good appliances and was very clean. Owners made it a point to communicate throughout! "
The price is CA $243
CA $546 total
includes taxes & fees
Jan 23 - Jan 24, 2025
King Bed/Fast Wi-Fi/Spacious/Family-Friendly/Just 2 steps to enter House

Great place to stay in Warrenville

10.0 out of 10, Exceptional, (47)
"We stayed here over Thanksgiving week, as none of our families have homes big enough to house us. The property was AMAZING! Very clean, nice little details like snacks and bottled waters in the refrigerator upon arrival. The beds were comfortable, the linens and pillows very nice. Everything was fantastic. We would stay again."
Great place to stay in Warrenville

Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath

10.0 out of 10, Exceptional, (88)
"We had a fantastic trip, house great for us Cary was very helpful "
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath

Full Luxurious Modern House Near Chicago

3.4 out of 10, (6)
"I stayed in this home for two nights. It was cold as ever. The heat did not work at all, no matter how high I turned it up and I couldn’t even heat up my food in the microwave because that didn’t work either. My food was not getting warm no matter how long I put it on in the microwave me and my company was cold For both nights."
Full Luxurious Modern House Near Chicago

Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago

8.2 out of 10, Very good, (20)
"We really love the home and the setup."
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

9.8 out of 10, Exceptional, (12)
"We really enjoyed this beautiful home and location for our family trip. The large rooms and open floor plan were perfect for six adults to enjoy. Plenty of local restaurants and shopping nearby. This was also a nice safe neighborhood for evening strolls and we enjoyed the Christmas lights on display."
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

UP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)

9.6 out of 10, Exceptional, (5)
"Our group consisted of 8 people ranging from preteens to octogenarians and we all really enjoyed this townhome! It was attractive, clean, updated and stylish, yet retained some of the historic ambiance of the neighborhood. Beds were comfy. Bedrooms are attractively decorated. Kitchen was roomy and easy to work in. Aga stove was a new experience, but after a short learning curve, we mastered it. The youngest members claimed the top floor as their space, which worked well. The home is a short walk...
UP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)

Modern Home in Trendy Neighborhood 40 from Downtown Chicago

9.6 out of 10, Exceptional, (12)
"Beautiful nice clean home , nice neighborhood very quiet and safe Host was nice and replied quick! Loved the home will be back !"
Modern Home in Trendy Neighborhood 40 from Downtown Chicago

Big Family Home with 4 King Beds

10.0 out of 10, Exceptional, (1)
"The host did an excellent job of allowing a most pleasurable experience. Syed was very communicative and responsive. The property is just as advertised and we enjoyed ourselves immensely. We will be back!"
The price is CA $412
CA $1,081 total
includes taxes & fees
Dec 29 - Dec 30
Big Family Home with 4 King Beds

Cozy 3-bedrooms w/ full kitchen bungalow in Chicago area (15-mins to downtown)

2.0 star property
5.4 out of 10, (3)
"We called and asked was small gatherings allowed and they said yes and they still managed to call police and kick us out "
The price is CA $294
CA $515 total
includes taxes & fees
Jan 2 - Jan 3, 2025
Cozy 3-bedrooms w/ full kitchen bungalow in Chicago area (15-mins to downtown)

Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

2.0 star property
10.0 out of 10, Exceptional, (2)
"Very clean in a safe neighborhood. I would stay here again"
The price is CA $229
CA $315 total
includes taxes & fees
Dec 30 - Dec 31
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
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, (630)
"The view was excellent "
The price is CA $157
CA $227 total
includes taxes & fees
Jan 12 - Jan 13, 2025
Sentral Michigan Avenue

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (344)
"Great stay "
Kasa Magnificent Mile Chicago

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (408)
"Outstanding accommodations! Will choose this property again for my travels."
The price is CA $180
CA $212 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Sonder South Wabash
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.