Holiday Homes in Southwest Side

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Featured Holiday Homes in Southwest Side

Enjoy cooking in this well-equipped kitchen with a double sink, oven, and dishwasher.

"The place was perfect for our stay in Chicago!"

Enjoy cooking in this well-equipped kitchen with a coffee maker and ample countertop space.

"This is a really cute property close to a lot of neighborhood restaurants and bars. The host is really nice and even moved his car for us so we could have his spot when we arrived. We would definitely stay here again. "

Enjoy meals in this dining area with a wooden table, white chairs, and a large mirror.

"Great place"

includes taxes & fees

5 Aug - 6 Aug

"Loved the place and host was super helpful when needed! "

Stunning single-family home with a backyard surrounded by mature trees and a well-manicured lawn.

"Clean and in a nice neighborhood "

Enjoy cooking in this well-equipped kitchen with a large island, dishwasher, oven, microwave, and coffee maker.

"Easy to get to and very clean. Also check in and out was easy as well. "

Relax by the fire pit in this serene outdoor space, surrounded by comfortable seating and lush greenery.

"Lots of good food and close to transit! Amazing little spot."

"Property manager was very responsive and the communication was clear and helpful. The house was very clean. Although the neighborhood was very concerning, dirty with a lot of people standing on the block, no one was threatening and nothing happened during our stay. Parking on street was safe. "

Enjoy cooking in this well-equipped kitchen with a microwave, oven, refrigerator, sink, and coffee maker.

"Great location in a beautiful part of town. Walk to Wrigley. Place was great for 2 families to hang out. "

Stroll up to this charming two-story home with a welcoming front porch and central chimney.

"We enjoyed this old house! It was clean & furnished well. Owner very accessible & easy to work with. Would definitely stay here again!"

Enjoy cooking in this well-equipped kitchen with a large window and stainless steel appliances.

"The large number of bedrooms provides privacy for a lot of people."

"Three weeks later tries to say we didn't pay when we have emails/proof saying otherwise. We checked in at the time, and some guy just comes in the backdoor with towels. Upon checkout, says we didn't leave the key & they had to get a locksmith - we literally saw someone come in with a key (man with towels at check in). Scary neighborhood, misleading advertising, terrible communication. "

Enjoy cooking in this well-equipped kitchen with oven, microwave, and stovetop.

"It’s a beautiful home, it had everything we needed. It was nice and comfortable!!! Me and my family enjoyed our stay!!!"

Enjoy a day at the beach with access to the ocean and scenic views.

"The property itself was ver clean just an older house. Very clean! The neighborhood was a little questionable for families who have never travelex to that area from a rural area. The stay was good and worked for what we needed!"

includes taxes & fees

28 July - 29 July

Enjoy cooking in this well-equipped kitchen with an island and stainless steel appliances.

"Very comfortable home. Location was great. Owners were very responsive and helpful. A storm on our last day unfortunately left us without power, owner was great at keeping us informed of status. Already went to book for our next trip but someone beat us to it. "

Enjoy cooking in this well-equipped kitchen with a stainless steel stove, microwave, and sink with a dish rack.

"The house was in a nice neighborhood and was very roomy and comfortable. Will be back."

Enjoy cooking in this well-equipped kitchen with a stainless steel stove, microwave, and black cabinetry.

"The space - number of rooms and bathrooms - was great for a big group. We were able to sleep multiple families comfortably with no issues getting ready with the number of bathrooms. There was plenty of free street parking close, so we also didn't have any problems finding parking for all our cars. Some more specific instructions on how to use the key pad (to enter and lock) would be helpful, but otherwise no complaints! I would recommend this Vrbo! "