Vacation rentals in South Side

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Popular amenities for South Side vacation rentals

Other great vacation rentals in South Side

Superhost
Home in Chicago
4.92 out of 5 average rating, 38 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

AshleyRating, 5 stars1 month ago
Johanna made us feel warm and welcome. All amenities are included and work well. Excellent shower. She was very responsive and attentive.
Guest favorite
A modern living space is presented with a white sofa and two accent chairs, arranged around a minimalist coffee table. A dining area is visible in the background, featuring a gold and glass table set with decorative items. Natural light filters in through large windows.
Home in Chicago
5 out of 5 average rating, 5 reviews

Birthday?Anniversary?Showers?3500 sq ft, sleeps 16

ArissRating, 5 stars1 week ago
Vince’s place was amazing, it was such a good location, easy to drive to anywhere in Chicago. Vince was very easy to contact and was responsive within minutes. He made our stay very comfortable. The house was amazing and there was a lot of space, and there was a lot of amenities available for use, for example kitchen utensils and shower amenities. Overall this stay was amazing and I would book this again if I came back in the future
Guest favorite
A cozy living area is presented, featuring a stone fireplace as a focal point. Two armchairs are positioned around a coffee table, with decor additions providing a touch of greenery. Natural light enters through nearby windows, illuminating the light-colored walls and hardwood floors.
Apartment in Chicago
4.86 out of 5 average rating, 42 reviews

Elegant 4Bedroom with Free Parking in Albany Park

MatthewRating, 5 stars2 months ago
Wonderful stay as always, thank you so much!
Superhost
A modern kitchen is equipped with sleek stainless steel appliances, including a microwave and dishwasher. Light countertops complement dark cabinetry, while a small countertop with two barstools provides a casual dining option. Natural light filters in through a window near the door.
Apartment in Chicago
4.63 out of 5 average rating, 24 reviews

City Gem: Stylish 3BR for Urban Explorers

AnnikaRating, 5 stars3 weeks ago
Peaceful, felt like home, very spacious and comfortable
Superhost
The exterior of a three-story Art Deco building is showcased, featuring a light-colored brick facade and large, symmetrical windows. A wrought iron fence surrounds the property, with well-maintained greenery enhancing the entrance. The sky above offers a clear blue backdrop.
Condo in Chicago
4.79 out of 5 average rating, 29 reviews

Spacious condo with open floor plan and fireplace

TatianaRating, 5 stars3 months ago
This place was spacious and perfect for our family (two kids and a baby), with plenty of room for everyone to spread out. The hosts were fantastic! They encountered an issue with the fridge not working just before our arrival but handled it professionally, providing excellent support until it was fixed. We really appreciated their responsiveness and care. We highly recommend this space for families and large groups. One small suggestion: if you’re a light sleeper or have kids, consider bringing a noise machine, as some sound from the upstairs neighbors can be heard. However, this wasn’t a problem for us and is to be expected when staying in a condo.
Top guest favorite
A modern kitchen area features a white bar counter with four dark wooden stools. Minimalistic tableware is arranged on woven placemats. Large windows allow natural light to fill the space, showcasing a glimpse of the outdoors through the decorative glass door.
Home in Lombard
5 out of 5 average rating, 25 reviews

Spacious Home in Chicago Suburbs

JenniferRating, 5 stars1 week ago
It was great! The house was lovely and looked newly renovated. It was much roomier than I expected. The beds were very comfortable.
Superhost
A well-equipped kitchen features light grey cabinetry and stainless steel appliances. A gas stove and microwave are prominently displayed, alongside a sleek black refrigerator. Natural light enters through a window, illuminating the countertop space, which is arranged with kitchen essentials and decorative accents.
Apartment in Merrillville
4.83 out of 5 average rating, 88 reviews

Lovely 2 Bed Room Apartment, all to yourself

BiancaRating, 5 stars2 weeks ago
the apartment was extremely cozy and we loved it it had everything we needed and cornelius has been an incredible host always ready to answer our questions
Top guest favorite
A spacious basement living area is highlighted by a comfortable gray sectional sofa facing a wall-mounted television. Soft lighting provides a cozy ambiance, while light-colored wood flooring runs throughout. Small decorative items are arranged on a side table, and windows offer natural light.
Home in Chicago
5 out of 5 average rating, 20 reviews

Comfy Home Away From Home

ZakiRating, 5 stars1 week ago
This home completely transformed our view of Chicago. We arrived a little nervous, but the moment we walked in, we were greeted by a space that was warm, welcoming, and absolutely stunning. Every detail was thoughtfully curated, from the sleek kitchen to the plush pillows on the sectional. The kitchen is modern and fully stocked, perfect for cooking and gathering. The living room is beautifully styled and cozy, and the bedrooms felt like luxurious retreats with spa-like linens and calming decor. The basement lounge was a standout with its oversized sectional and elegant bar area, so perfect for relaxing after a long day. We especially loved the little reading nook with the blue chairs. Every corner of this home radiates peace and intentionality. It truly felt like a sanctuary. We left feeling inspired, rested, and already planning our return.

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