Vacation rentals in South Side

5 out of 5 average rating, 13 reviews

The exterior of a historic brownstone building is showcased, featuring a beautifully detailed entrance surrounded by brick and stone. A set of steps leads up to the front door, flanked by decorative wrought iron railings and lush greenery, creating a welcoming atmosphere.

Home in Chicago

Top Floor in Historic Old Town!

KristenRating, 5 stars2 days ago

Heather’s place was perfect. It was very quiet which is an absolute for us when we travel. The location was also great for visiting my family in Lincoln Park. Easy walking to armitage shops, restaurants etc. I appreciated that Heather provided parking stickers and street parking was very easy. I will definitely book again.

4.85 out of 5 average rating, 68 reviews

A cozy living room features four plush purple chairs arranged around a circular table. A modern television is mounted above a white brick fireplace, complemented by bookshelves filled with various items. A large potted plant adds a touch of greenery, enhancing the warm atmosphere.

Home in Oak Park

A Comfortable Stay While You are Away in Oak Park

KarenRating, 5 stars3 weeks ago

The house looked just like the beautiful photos & Jay was incredibly responsive throughout the visit. This home is located close to 290 to go downtown or further out to the 'burbs quickly. We needed a home to stay last minute, and Jay was accommodating to that as well - we were happy to find this spot with all the space we needed inside and out. As a bonus, we met neighbors who were very friendly.

4.85 out of 5 average rating, 34 reviews

The exterior of the tiny house is shown, featuring a light grey façade with two symmetrical windows on the upper level and a white door at the bottom. A wooden staircase leads to the entrance, surrounded by minimal landscaping and a clear blue sky above.

Guesthouse in Evanston

Tiny house in West Village Arts District

JoelRating, 5 stars4 months ago

Lisa was a great host and this is a great place. It's a small house, but worked great for what we needed it for and was close to our family that live in Evanston. It was also a great price. Additionally, there were games which was nice because we had our child with us. I would definitely recommend this place and I will be staying here again when we're in Evanston, hopefully Lisa's schedule will be open!

Guest suite in Naperville

A scenic view of a tranquil lake is framed by vibrant yellow pansies in planters. Lush green grass extends to a black fence bordering the water, while trees and distant greenery create a peaceful backdrop under a blue sky.

4.95 out of 5 average rating, 415 reviews

Cozy Lakeview Studio with Private Access

JunikaiRating, 5 stars2 days ago

Sanjay and Aparna were amazing and so was the room. You can tell just from the unpacking-phase of your visit that this location was well thought out and planned. They provide as much as they can in the unit accordingly before you arrive to make sure you are comfortable and set. You feel very safe in the unit itself and in the area you will be residing in temporarily. Not to mention the beautiful lake right outside your door! 10/10, 100% would visit again

4.95 out of 5 average rating, 104 reviews

A modern kitchen features sleek dark cabinetry and stainless steel appliances. Natural light enters through skylights, highlighting a small dining table with two chairs. The warm wood flooring complements the design, while a light fixture hangs gently from the exposed beam ceiling.

Guesthouse in Oak Park

O'Malley Oasis!

AndreaRating, 5 stars4 months ago

Clean, beautiful space. Has everything needed and the most comfortable seating space to relax. Clear instructions, easy parking. Be aware that there are several stairs to enter as seen in the pictures. They are well maintained with a handrail. This was not an issue at all for us but could be for someone with mobility limitations. Otherwise one of the best places I have stayed in Oak Park. Hope it is available when I come back.

4.96 out of 5 average rating, 281 reviews

The exterior of a three-story residential building is depicted, featuring a wooden porch with steps leading to the front door. Large windows allow natural light to enter, and greenery surrounds the entrance, complementing the light-colored siding and red brick foundation.

Apartment in Chicago

Spacious 1BR apartment in a central location

GilRating, 5 stars1 month ago

I have stayed in a number of AirBnB‘s throughout the years, this may have been my favorite stay. There is absolutely everything you would need for a comfortable stay. Everything is clean. Alex is a five-star communicator. It is a busy little neighborhood, but the bedroom is toward the back of the apartment. I heard nothing but dead silence at night.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for South Side vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in South Side

4.93 out of 5 average rating, 40 reviews

Home in Chicago

Family Friendly Duplex/9 min from MDW/Free Parking

JoannaRating, 5 stars3 weeks ago

Came for c2e2 with my friends and it was perfect for all of us! Would recommend 💗💗

4.86 out of 5 average rating, 42 reviews

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

Elegant 4Bedroom with Free Parking in Albany Park

MatthewRating, 5 stars2 months ago

Wonderful stay as always, thank you so much!

4.63 out of 5 average rating, 24 reviews

A modern dining area is highlighted by a wooden table surrounded by four chairs. The open-concept layout connects to a stylish kitchen featuring dark cabinetry and stainless steel appliances. Natural light fills the space, reflecting off the hard surface flooring and a cozy living room in the background.

Apartment in Chicago

City Gem: Stylish 3BR for Urban Explorers

AnnikaRating, 5 stars1 month ago

Peaceful, felt like home, very spacious and comfortable

4.79 out of 5 average rating, 29 reviews

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

Spacious condo with open floor plan and fireplace

TatianaRating, 5 stars4 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.

5 out of 5 average rating, 25 reviews

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

Spacious Home in Chicago Suburbs

JenniferRating, 5 stars3 weeks ago

It was great! The house was lovely and looked newly renovated. It was much roomier than I expected. The beds were very comfortable.

5 out of 5 average rating, 5 reviews

The exterior of the home is showcased, featuring a wooden facade, a prominent balcony above large windows, and a spacious driveway. Soft landscaping surrounds seating arrangements near the entrance. A garage structure is visible to the right, with trees and open space in the background.

Home in Wood Dale

Home in the Woods!

DevynRating, 5 stars1 week ago

We stayed here for my Bachelor Party. It was a golf trip, so having the Preserve at Oak Meadows right next door was great. Jazmin was responsive when we had a small issue with the code to get in. All-in-all a great place!

Apartment in Merrillville

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.

4.83 out of 5 average rating, 89 reviews

Lovely 2 Bed Room Apartment, all to yourself

OlumideRating, 5 stars1 week ago

I had a wonderful 2-night stay at this property! The host was extremely polite and very responsive, making the entire experience smooth and stress-free. The home itself was in immaculate condition — spotless, well-maintained, and just as beautiful as the pictures online, if not better. I would highly recommend this place to anyone looking for a comfortable and hassle-free stay. Thank you for a great experience!