Orland Park Vacation Rentals

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Check prices for these dates

Next weekend
Feb 7 - Feb 9
In two weeks
Feb 14 - Feb 16
In one month
Feb 28 - Mar 2
In two months
Mar 28 - Mar 30

Browse Select Orland Park Vacation Homes

Spacious 3br home near Chicago, fenced yard for pets
Fridge, microwave, oven, stovetop

Spacious 3br home near Chicago, fenced yard for pets

2.0 star property
10.0 out of 10, Exceptional, (2)
"Awesome stay!"
The price is CA $173
CA $442 total
includes taxes & fees
Feb 2 - Feb 3
Spacious 3br home near Chicago, fenced yard for pets
Charming 3-bedroom house in Calumet City with WiFi and AC
Private kitchen

Charming 3-bedroom house in Calumet City with WiFi and AC

10.0 out of 10, Exceptional, (3)
"Tammara is a perfect host! She is nice and accommodating. The check in process was very smooth. The house was spotless and so nice! I will definitely be booking again. "
The price is CA $216
CA $415 total
includes taxes & fees
Feb 6 - Feb 7
Charming 3-bedroom house in Calumet City with WiFi and AC
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
Fridge, microwave, oven, stovetop

Gorgeous historic mansion on UChicago campus. Renovation with original detail.

10.0 out of 10, Exceptional, (3)
"I wish we came across this property 4 years ago when we dropped off our daughter at the UofC campus. Location is amazing, 7 minutes walk to the campus. The house is spacious and accommodates a large group of people. Very clean and what was really appreciated it was so well stocked - nice shampoos and lotions in all bathrooms, paper towels in the kitchen, a welcome bottle of bubbly wine from the hosts. The check-in and out process was also incredibly easy, and the hosts were very welcoming and...
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
Luxury Home Away From Your Home
Fridge, microwave, oven, stovetop

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (116)
"Had a great time at Ms. Linnie’s place! She was incredibly responsive and helpful. The house was clean and comfortable, and I loved that there were 2 full bathrooms! I was a little nervous about the neighborhood as we were definitely looked at as outsiders, but no one bothered us and we walked to Maxwell Street Polish and back just fine (which is fantastic, btw). I did love the gated yard in back with two parking spots, so we had our own space. Would definitely stay again!"
Luxury Home Away From Your Home
Cheerful 4 bedroom smart home w/ indoor fireplace
Fridge, microwave, oven, stovetop

Cheerful 4 bedroom smart home w/ indoor fireplace

7.8 out of 10, Good, (12)
"Loved the place and host was super helpful when needed! "
Cheerful 4 bedroom smart home w/ indoor fireplace
Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!
Private kitchen

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!
Berwyn Beauty
Fridge, microwave, oven, stovetop

Berwyn Beauty

10.0 out of 10, Exceptional, (12)
"Perfect for visiting family by with more space than an hotel. A nice neighborhood. Away from the hustle and bustle of downtown but an easy drive for vacationers. "
Berwyn Beauty
Stunning 4-bedroom 4-bath building in Wicker Park! + Parking
Terrace/patio

Stunning 4-bedroom 4-bath building in Wicker Park! + Parking

Stunning 4-bedroom 4-bath building in Wicker Park! + Parking
LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins
Microwave, oven, stovetop, dishwasher

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

9.4 out of 10, Exceptional, (3)
"Good stay. "
LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins
The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking
Fridge, microwave, oven, stovetop

The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking

9.6 out of 10, Exceptional, (46)
"The home was updated and very clean. The kitchen was large and was well stocked. The owner provided everything you would need to cook. The fenced in yard was a bonus as we traveled with our dog. The neighborhood is older and safe. The neighboring homes are well maintained. The street in front of the house is busy during rush hour, but didn't create an issue pulling out into traffic. We did not experience noise from the traffic. We had one small glitch which was taken care of quickly. The...
The price is CA $229
CA $512 total
includes taxes & fees
Feb 24 - Feb 25
The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking
Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym
Interior

Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym

10.0 out of 10, Exceptional, (3)
"Upscale tri level home, easy location to get to and Uber from. House is very well designed and set up for a larger family group. 4 nice bedrooms with really nice bathrooms and a small workout area. Living room and kitchen open up to a back deck area with lower level sitting spaces. Great place to stay for concerts or just an easy location to visit the pier or soldier field or Wrigley or white Sox. We enjoyed our week. "
Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym
LUXE 3 BR, 2 BA + Hot Tub
Private kitchen

LUXE 3 BR, 2 BA + Hot Tub

9.2 out of 10, Wonderful, (21)
"Hot tub was nice, the house itself was clean and had a great backyard that is big and pretty. Host is very responsive. Recommend!!"
The price is CA $396
CA $656 total
includes taxes & fees
Feb 3 - Feb 4
LUXE 3 BR, 2 BA + Hot Tub
Spacious 5-bedroom house with movie room, game room and more!
Fridge, microwave, oven, stovetop

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!
Furnished Private home in Aurora sleeps 9 guests
Fridge, microwave, oven, stovetop

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
Cozy 5-bedroom with lake views and spacious deck
Outdoor dining

Cozy 5-bedroom with lake views and spacious deck

10.0 out of 10, Exceptional, (8)
"This was our 2nd year in a row staying here. Everything was great yet again. I highly recommend this house for anyone staying in the area."
Cozy 5-bedroom with lake views and spacious deck
Cozy 3-bedroom house in family-oriented Melrose Park.
Interior

Cozy 3-bedroom house in family-oriented Melrose Park.

Cozy 3-bedroom house in family-oriented Melrose Park.
Luxe Downtown Historic Victorian, A+ Location. Spacious 4-bedroom near Chicago!
Shower, jetted tub, hair dryer, towels

Luxe Downtown Historic Victorian, A+ Location. Spacious 4-bedroom near Chicago!

10.0 out of 10, Exceptional, (1)
The price is CA $583
CA $721 total
includes taxes & fees
Feb 3 - Feb 4
Luxe Downtown Historic Victorian, A+ Location. Spacious 4-bedroom near Chicago!
Beautiful and updated place to stay in a quiet neighborhood of Munster Indiana.
Fridge, microwave, oven, stovetop

Beautiful and updated place to stay in a quiet neighborhood of Munster Indiana.

10.0 out of 10, Exceptional, (16)
"The house was in a great location, plenty of parking, inside was very spacious with everything we needed and a minimalist set up which was nice with the dogs and not feeling crowded. The yard was huge and fully fenced in for the dogs. We would stay again if needed. Thank you!"
Beautiful and updated place to stay in a quiet neighborhood of Munster Indiana.
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago
Fridge, microwave, stovetop, dishwasher

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
Full Luxurious Modern House Near Chicago
Private kitchen

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
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
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (669)
"Sandra and Joy are welcoming and helpful. Great front desk."
The price is CA $158
CA $228 total
includes taxes & fees
Feb 2 - Feb 3
Sentral Michigan Avenue
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (250)
"Easy to find.Had to drive around a little to find parking, but it worked out fine. Easy access with a code or using the Sonder app.Comfortable bed. Very clean room. We did not have any issues with the night club downstairs, but our room was on the 5th floor. The train goes by right next door, but it was kind of a soothing sound. I would definitely stay here again. "
The price is CA $163
CA $191 total
includes taxes & fees
Feb 20 - Feb 21
Sonder Market Hall
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (426)
"Property was convenient and clean. Overall great experience. Street meter parking could be a headache during parking hours but it’s a city thing. Also the incidental feee is a bit confusing with how it’s returned. "
The price is CA $137
CA $161 total
includes taxes & fees
Feb 25 - Feb 26
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.