Search Vacation Homes in Orland Park

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 458 Vacation Homes in Orland Park with updated reviews, rates, and availability.

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 | Fridge, microwave, oven, stovetop
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
Save an average of 15% on thousands of hotels when you're signed in
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 $200
$310 total
includes taxes & fees
May 29 - May 30
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 $170
$289 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 $300
$345 total
includes taxes & fees
May 30 - May 31
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 $105
$260 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
Don't see what you're looking for?
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)
"The front desk staff were incredibly helpful, cheerfully assisted me with check-in and stored my extra bags early in the day when I went to work on the day u checked out. A service."
The price is $159
$216 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 $139
$163 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 $194
$228 total
includes taxes & fees
Jun 5 - Jun 6
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
$105
Highest Price
$300

Recent reviews of Orland Park hotels
Expedia verified reviews