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Compare 44 Condo Rentals in Highland with updated reviews, rates, and availability.

Penthouse Condo in Chicago featuring Zero Gravity Massage Chair
10.0 out of 10, Exceptional, (10)
"👍"
Penthouse Condo in Chicago featuring Zero Gravity Massage Chair
The Chic Urban Retreat Near the Lake!
10.0 out of 10, Exceptional, (1)
"Loved the place - stayed for the Air Show and we were close enough to get everywhere quickly!"
The Chic Urban Retreat Near the Lake!
♛The Broadway Special♛ - 2 Bd/1 Bath Smart-Condo!
10.0 out of 10, Exceptional, (15)
"Have stayed here multiple times. We always have a good experience. It would have been very helpful to have kitchen towels. I do most of my own cooking & hand wash the dishes."
♛The Broadway Special♛ - 2 Bd/1 Bath Smart-Condo!
Lovely Quiet, Safe 6-Bedroom in 2 Condos Suite by McCormick Place and Midway!
10.0 out of 10, Exceptional, (2)
"11 family members in Chicago for a wedding. Enough beds for everyone in the two condos located one above the other. Very convenient."
Lovely Quiet, Safe 6-Bedroom in 2 Condos Suite by McCormick Place and Midway!
Bronzeville Manor walking distance to hospitals
10.0 out of 10, Exceptional, (11)
"Great location, very clean place. Ample street parking and the owner is very nice. I’ll definitely be booking this location again."
Bronzeville Manor walking distance to hospitals
Modern Condo-Obama & University of Chicago Area
Modern Condo-Obama & University of Chicago Area
Comfortable Condo in the Heart of Bronzeville by RedAwning
5.0 out of 10, (2)
"There was confusion with VRBO regarding our arrival date, no fault of the property owner. They made arrangements to clean the unit and provide lunch for our group while we waited and offered a second night free for the inconvenience. Highly recommend. Property owner went above and beyond!"
The price is AED 503
AED 1,624 total
includes taxes & fees
1 Oct - 2 Oct
Comfortable Condo in the Heart of Bronzeville by RedAwning
Newly Built Condo: 5 Mi to Downtown Chicago!
10.0 out of 10, Exceptional, (2)
"I was pleased with the upscale interior and the neighborhood but sort of mislead of the distance to the United Convention Center. It was not accessible by metro train. Still, we were able to Uber to and from with safety late at night. There was difficulty accessing the key upon arrival and difficulty returning it to the lockbox. On the day of departure, I noticed a water leak from the vent in the master bathroom that appeared to have been there for a while. We were leaving that day, so that it...
Newly Built Condo: 5 Mi to Downtown Chicago!
Luxury Waterfront 2 Bedroom Condo by Lake Michigan
10.0 out of 10, Exceptional, (12)
"We liked how clean and well decorated the condo was. The pool was nice, and the train close by was a bonus. We went to Indiana Dunes national park and to Chicago during our stay."
Luxury Waterfront 2 Bedroom Condo by Lake Michigan
LONG STAY, 4 bd, Free Park, 2 miles to Hyde Park
10.0 out of 10, Exceptional, (1)
"We had a great time visiting Chicago. The property was well designed and cozy, a home I'd live in. The host was very nice, responsive, and accommodating. Would stay there again on another visit!"
LONG STAY, 4 bd, Free Park, 2 miles to Hyde Park
Spacious two bedroom condo with a cozy feel!
8.0 out of 10, Very Good, (4)
"Very nice amenities. Comfortable beds."
Spacious two bedroom condo with a cozy feel!
Serenity on the Shores - with easy transport to Chicago/SouthShore across the St
10.0 out of 10, Exceptional, (2)
"Very nice"
Serenity on the Shores - with easy transport to Chicago/SouthShore across the St
Historic Washington-Hyde Park Greystone
10.0 out of 10, Exceptional, (3)
"The apartment was very nice, well decorated and equipped, thoroughly cleaned and easy to access. Will definitely stay there again if I'm in the area!"
Historic Washington-Hyde Park Greystone
Lovely 2 Bedroom Condo With Pool
Lovely 2 Bedroom Condo With Pool
420 zen environment surrounded by boho chic decor~Luv Happii House.
10.0 out of 10, Exceptional, (1)
"My stay at the Luv Happy House was the perfect getaway for my birthday. The house looks exactly like it is listed which is so beautiful! I loved everything about this place nd the host was very responsive, even when i called her at 11:00pm because I had a hard time finding the place. She directed me until i got there, I will definitely stay here again."
420 zen environment surrounded by boho chic decor~Luv Happii House.
A luxury vintage condo close to lakefront and minutes from downtown!
A luxury vintage condo close to lakefront and minutes from downtown!
Luxury Stay on UChicago Campus 11 min walk to hospitals
10.0 out of 10, Exceptional, (1)
"We couldn't have found a better accommodation for our four-day visit to Hyde Park, than this newly renovated property on Ingleside. Literally a few minutes' walk from the quad of UofC, the three-bedroom, two full bathroom unit was more than ample space for our two couples hoping to have ease of access to the University and the restaurants and shops of Hyde Park. The modern kitchen had everything we needed, and the living room was spacious with study desk and entertainment seating. The whole...
Luxury Stay on UChicago Campus 11 min walk to hospitals
Oak Lawn big 2nd floor Condo for 8 ppl 3 bedroom 2 bath Sofa bed Garage Parking.
Oak Lawn big 2nd floor Condo for 8 ppl 3 bedroom 2 bath Sofa bed Garage Parking.
King Bed Suite | Indoor Pool. Free Breakfast.
King Bed Suite | Indoor Pool. Free Breakfast.
MODERN 2 BEDROOM CONDO! WHEN LUXURY & COMFORT MEET!
8.8 out of 10, Excellent, (5)
"pictures do not do justice…nice place i especially loved the living room concept i would stay here again for sure"
MODERN 2 BEDROOM CONDO! WHEN LUXURY & COMFORT MEET!
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Other property types in Highland

Casa Blanca in Miller Beach!
9.8 out of 10, Exceptional, (64)
"This is our 2nd year to rent this lovely home. It is so spacious and enough room for our family. A well equiped kitchen, and plenty of seating for us to eat and play table games. Comfy beds. There are areas to sit and read or sit on the porch or do a puzzle. The piano is a plus. Lots of inside activitties, pool, pingpong, air hockey table for the kids if the weather is not favorable. An easy walk to the beach, great bike path nearby, frisbee golf, and hot tub. "
Casa Blanca in Miller Beach!
LakeHouse
10.0 out of 10, Exceptional, (11)
"We chose this place to stay off the congested highways & expensive toll roads & it provided easy daily drives to & from McCormick Place for week-long trade show via DuSable Lakeshore Drive. House & parking were as advertised & secure, no issues. "
LakeHouse
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
9.8 out of 10, Exceptional, (7)
"This rental is right by Indiana Dunes and in a nice neighborhood. Main bed was comfortable and we slept well. The shower needs repaired. There was not a cloth to wash dishes with. The skillet in the cabinet still had food in it. We did walk around the block to get Uno Pizza which is in a speakeasy setting. Nice place. It was early for swimming but we did take a dip. Don let us stay late to enjoy the sun. The pool is well cared for. Overall a good rental."
The price is AED 437
AED 572 total
includes taxes & fees
29 Sep - 30 Sep
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
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.

Frequently asked questions

How much do condos in Highland cost?
Prepare to pay from AED390 to AED390 per night for condos in Highland. Whatever your budget, the perfect stay is a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Highland?
Use up your vacation days and pick from 44 condos in Highland. For business travel, a family getaway and everything in between, Expedia can help you find the right place in just a few clicks.
Why book your condo in Highland with Expedia?
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