Orland Park Vacation Rentals

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Browse Select Orland Park Vacation Homes

TV
Luxury Downtown Penthouse with Private Rooftop!
10.0 out of 10, Exceptional, (4)
"Good host"
Luxury Downtown Penthouse with Private Rooftop!
Property grounds
Breathtaking Downtown Penthouse B - Sleeps 11
10.0 out of 10, Exceptional, (3)
"This property was very clean and spacious and close to everything we needed to be walking distance from. Parking was easy and extra parking was cheap and affordable."
Breathtaking Downtown Penthouse B - Sleeps 11
Private kitchen
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (106)
"The host communicated well. The area was busy but felt safe. I felt it was expensive for the location. Very clean."
Luxury Home Away From Your Home
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Property grounds
Breathtaking Downtown Penthouse A - Sleeps 11!
9.0 out of 10, Wonderful, (2)
"We stayed here with 6 adult friends for a concert and really enjoyed our stay. The rooftop area you have all to yourself and was a big hit within our group. It is a short 15-20 minute walk from lots of fun things to do like kayak the river, an animal rescue that you can go pet dogs and the Original Mr. Beef restaurant that the show "The Bear" is based off of. We went to Mr.Beef for great sandwiches and even saw the main actor from the show there!! For sleeping arrangements, it wasn't ideal to...
Breathtaking Downtown Penthouse A - Sleeps 11!
Private kitchen
LUXE 3 BR, 2 BA + Hot Tub
9.2 out of 10, Wonderful, (9)
"Our team had a one day conference in Chicago. Although it was near the highway it wasn't very loud. Decent neighborhood and the good part is that it was near the highway. Lower level bed is uncomfortable, no other way to say that. I still give it 5-stars as it is as advertised. Communication with owner was timely."
The price is CA $273
CA $422 total
includes taxes & fees
May 28 - May 29
LUXE 3 BR, 2 BA + Hot Tub
Property grounds
✽ Charming Cottage ✽ close to College/Town/Station
10.0 out of 10, Exceptional, (31)
"Great house thank you"
The price is CA $232
CA $395 total
includes taxes & fees
Jun 25 - Jun 26
✽ Charming Cottage ✽ close to College/Town/Station
Outdoor dining
national historic home near downtown airports no parties no events
9.4 out of 10, Exceptional, (19)
"Had a great time used space for birthday event!!"
The price is CA $410
CA $472 total
includes taxes & fees
May 28 - May 29
national historic home near downtown airports no parties no events
Exterior
Cozy, King bed with heated bathroom!
9.8 out of 10, Exceptional, (8)
"Great"
Cozy, King bed with heated bathroom!
Microwave, oven, stovetop, dishwasher
Furnished Private home in Aurora
9.4 out of 10, Exceptional, (56)
"We stayed over Mother's Day weekend. It was a lovely house with two large family areas and TVs in every room and access to our streaming apps. We were disappointed the yard was not mowed w/tall weeds. Some of the deck is starting to fall apart. It wasn't suitable for the 3-year-old to run around in. However, the neighbors did say that the landscaping had been kept up last year. But knowing we were coming, it would have been nice to have at least sprayed for the weeds. The sump pump hose has...
Furnished Private home in Aurora
Fridge, microwave, oven, stovetop
Updated Forest Park 3 BR Bungalow
10.0 out of 10, Exceptional, (84)
"This vrbo exceeded expectations from the photos. The vrbo was extemely clean, well maintained, and our dog enjoyed the yard. We also felt very safe walking at night and really enjoyed the proximity to Oak Park attractions, and the green line el stop is a 5 minute walk away. We intend to stay again when visiting the Chicago suburbs!"
Updated Forest Park 3 BR Bungalow
Interior
Elegant Mayor's Manor in Central Chicago - 9 Beds
9.6 out of 10, Exceptional, (8)
"Place was as described and worked perfect for our stay."
Elegant Mayor's Manor in Central Chicago - 9 Beds
Exterior
Charming Oak Park Home w/ Private Fire Pit!
9.8 out of 10, Exceptional, (8)
"Me and my family stayed there and it has to be my favorite place when visiting family there was more than enough room for local family members to come and visit, the beds were so comfortable and the place was stocked with everything we needed. Communication was perfect we had to stay an extra day and they let us book it with no problem. Would definitely book to stay at again."
Charming Oak Park Home w/ Private Fire Pit!
Property grounds
Stunning Duplex Condo #1 - Downtown River North
Stunning Duplex Condo #1 - Downtown River North
Private kitchen
Amazing 4 Bedrm Twnhm-30 Miles to Dwntwn Chicago Private Off Street Parking
10.0 out of 10, Exceptional, (2)
"My family really enjoyed this townhouse. It was very nice clean, location was perfect. Would definitely stay here again. The host Sherice was very very nice, kind, friendly and patient with my family."
Amazing 4 Bedrm Twnhm-30 Miles to Dwntwn Chicago Private Off Street Parking
Exterior
Modern, Spacious, & Convenient 4 BR/3.5 BA Home minutes from golf & shopping
9.8 out of 10, Exceptional, (29)
"Our stay at this VRBO rental was nothing short of exceptional! The location was perfect – safe, quiet, and conveniently situated. Syed was incredibly friendly and attentive, going above and beyond to ensure our needs were met. His proactive reminders helped us navigate the rental smoothly, avoiding any unnecessary charges. We felt well taken care of throughout our stay. The 8 of us (in town for a hockey tournament) had more than enough space. Without a doubt, this rental and Syed's hospitality...
Modern, Spacious, & Convenient 4 BR/3.5 BA Home minutes from golf & shopping
Fridge, microwave, oven, stovetop
Cozy Home Sweet Homewood.
10.0 out of 10, Exceptional, (4)
"Neighborhood was quiet! Rental was exactly as shown online. Was able to easily find the rental with no problem. Overall great stay."
Cozy Home Sweet Homewood.
Fridge, microwave, oven, stovetop
3 Flat Building Downtown - With Private Patios
9.6 out of 10, Exceptional, (5)
"This house allowed 30 people to stay comfortably sharing beds. The neighborhood requires ubering to other locations, but works for large groups. The house was fairly clean."
3 Flat Building Downtown - With Private Patios
Exterior
A quiet stay while you are away
9.8 out of 10, Exceptional, (26)
"Jay was a perfect host, house location was great, house was clean, neighborhood quiet. Jay supplied us with coffee, which we were not expecting - thanks Jay, that was a bonus. :). If and when I come back to Chicago I know where I will be staying. Thanks again Jay. Best, Maddie"
The price is CA $141
CA $352 total
includes taxes & fees
Jun 4 - Jun 5
A quiet stay while you are away
Fridge, microwave, oven, stovetop
Beautiful Home
10.0 out of 10, Exceptional, (3)
"Host was very communicative, house was very clean and provided bedroom, kitchen, and bathroom essentials which was a very nice surprise. Overall great place to stay very nice. "
Beautiful Home
Property grounds
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
10.0 out of 10, Exceptional, (78)
"Space was perfect for (small) adult family reunion. Lots of space to retreat to - and lots of space to be together. Plenty of Bathrooms for privacy. Kitchen / bath fixtures and finishes are great. A few spots that show the age of latest renovation - but overall still great. Bed/bedding was excellent. Location was nice for enjoying Fulton Market, River North, and the Loop. Contact with host was perfect: timely, cheerful, helpful. Would certainly do again"
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
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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.

Other property types in Orland Park

Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (412)
"This property gave me the feeling of being at home away from home. Very clean and safe and the staff was so welcoming. I definitely will be staying here again ! "
The price is CA $196
CA $270 total
includes taxes & fees
May 29 - May 30
Sentral Michigan Avenue
Interior
Sonder Market Hall
3.5 star property
8.2 out of 10, Very good, (85)
"I loved having the whole space to ourselves. Felt the privacy of the entire building, more than a hotel. It was great. Would probably book again!"
The price is CA $159
CA $187 total
includes taxes & fees
Jun 16 - Jun 17
Sonder Market Hall
City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (302)
"It was a pleasant stay"
The price is CA $258
CA $303 total
includes taxes & fees
May 28 - May 29
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.

Orland Park Vacation Homes information

Number of reviews
481
Accommodation
458 Vacation Homes
Lowest Price
CA $141
Highest Price
CA $410

Recent Reviews in Orland Park
Expedia verified reviews