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House holiday rentals in South Side

Find and book unique houses on Airbnb

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Popular amenities for house rentals in South Side

House rentals with a pool

Guest favourite
Home in Highland Park
4.91 out of 5 average rating, 145 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

MaryRating, 5 stars3 weeks ago
We had a great stay overall. From start to finish, Kailash was extremely helpful, friendly and responsive. We needed a long-term stay with 2 big dogs, and this house worked great for us. We didn't get to use the pool much because the weather didn't cooperate, but the pool and patio area are gorgeous. The location is great, close to everything - grocery stores, restaurants, etc. There is a trail behind the house (accessible through a gate in the back yard), and it leads to a beautiful and huge forest preserve - beautiful for walks/hikes in the woods! The kitchen was a great space for us, and it had everything we might need for cooking, etc. The house was very comfortable for our family, and we would come again. Thank you, Kailash!
Top guest favourite
Home in Schererville
4.95 out of 5 average rating, 56 reviews

Cozy house in Schererville

AnyaRating, 5 stars2 weeks ago
Very well thought through place for every detail, with a mix of 70s wood style and some higher tech upgrades like the main bathroom mirror with light and anti fog, or sensor lights. Kate was very responsive and accommodating for the 1 baby & 1 toddler we asked for. The place was stocked with all necessary items especially in the kitchen with appliances and cutlery, coffee, tea. There were 2 hairdryers, nice shampoo and conditioner, shower gel.
Guest favourite
Home in Munster
5 out of 5 average rating, 11 reviews

Munster hide away

ChristopherRating, 5 stars5 months ago
Nice house with updates. We used all four bedrooms, so everyone had their own space. Kitchen and living room looked nice, but a bit cozy if everyone was in the space at the same time. There was a large breakfast nook/counter in the kitchen instead of a table. More dishes, mugs, etc. in the kitchen would have been nice. The coffee maker and provided K-cups were great! Would definitely stay again if it's available when we are in the area again.
Superhost
Home in Des Plaines
5 out of 5 average rating, 4 reviews

Rosemont 4BD2BA house with Pool

HannahRating, 5 stars1 month ago
Mike was very responsive leading up to our stay and very helpful whenever I had any questions about the property. The home was very clean and well maintained. Would recommend!
Guest favourite
Home in Bloomingdale
4.92 out of 5 average rating, 51 reviews

Now Open: Heated Pool with Entire House

TaraRating, 5 stars1 month ago
Moizs was an amazing host. Very accommodating, quick response, had some great recommendations for local restaurants, shopping, etc. Bloomingdale is a cute and nice suburb of Chicago. We had a great trip and we will definitely be back.
Superhost
Home in Gary
4.83 out of 5 average rating, 36 reviews

Entire House With Pool - Backyard Beach Getaway

CrystalRating, 5 stars6 months ago
This home was super cozy for my big family. Everything was clean, comfortable, and the way it is set up makes you feel right at home. This home had everything we needed. TV’s, kitchen items, recommendations, and even fun family games and activities to do. Every time I visit the area I’ll be checking to see if it’s available. 10/10
Guest favourite
Home in Schaumburg
4.93 out of 5 average rating, 27 reviews

Schaumburg Oasis:Private Pool & Enchanted Garden

TeddyRating, 5 stars6 days ago
They were a fantastic host, very responsive to every question and anything we needed. The location is quiet and amazing, great place to relax and enjoy time. love the pool! Will definitely stay again. 100% recommend!
Superhost
Home in Chicago
4.88 out of 5 average rating, 56 reviews

Luxury Loft with Private Pool and Movie Theater

RyanRating, 5 stars6 days ago
Damani was a great host, really responsive and easy to communicate with! The house was exactly as advertised and really nice! The pool was great!

Weekly house rentals

Superhost
Home in Chicago
4.71 out of 5 average rating, 21 reviews

Lux_Home Chicago 8 mins Downtown

StephenRating, 5 stars1 day ago
Everything was exactly as pictured, and the space was clean and comfortable. The location is quiet, which made for a peaceful stay. Evan was an excellent host—accommodating, kind, and flexible. He responded promptly to any questions and made the experience seamless. Would definitely stay again!
Guest favourite
Home in Chicago
4.92 out of 5 average rating, 52 reviews

Cheerful 3 Bedroom, City Oasis

Jill And SunilRating, 5 stars1 week ago
We stayed at this property to attend our daughter’s graduation from UChicago. It was within walking distance of campus and all of the activities during the weekend. The street is VERY quiet. Parking was ample and easy. The house is immaculate and spacious. Very comfortable!
Guest favourite
Home in Chicago
4.88 out of 5 average rating, 51 reviews

CasaNova Modern City Living

HelenRating, 5 stars1 month ago
Beautiful home layout and very spacious! Location was a quick drive to the city, which was convenient. Host was also very kind and attentive. Thank you Ms. Lilly for our stay!
Guest favourite
Home in Chicago
4.93 out of 5 average rating, 44 reviews

Floresitas Oasis, your home in Chicago

Kawina RochelleRating, 5 stars1 day ago
Lizbeth was an amazing host. She’s responsive and attentive. The place was exceptional clean and had an amazing smell. I was there to celebrate my birthday and was pleasantly surprised upon entry when I was greeted with a personalized birthday message, fresh flowers and a bottle of wine. Anytime I reached out to Lizbeth, she responded expeditiously. Again, very attentive. My husband and I will definitely stay at her beautiful Oasis again. We felt comfortable and completely safe. Everything we wanted to do was a quick drive from the location. If you’re considering staying at her home, you will not regret it. If I could give more than 5 stars, I would. Thanks Lizbeth for being an incredible host Until the next time…
Superhost
Home in Chicago
4.83 out of 5 average rating, 71 reviews

Brand New Spacious Duplex

LillianRating, 5 stars1 week ago
I just wanna say thank to each other to host. It was nice and big. The bed downstairs was a little hard. The water stain around the basement floor area and it did smell like mold. Other than that. It was good value for your money. Parking was a challenge for us, but we figured it out. Have a great day if you stay.
Guest favourite
Home in Chicago
5 out of 5 average rating, 6 reviews

Charming 3 bed home with private backyard

ToniaRating, 5 stars1 month ago
I had an absolutely wonderful experience staying at this Airbnb! From the moment I arrived, everything exceeded my expectations. The place was spotless, beautifully decorated, and exactly as described in the listing—if not better. It felt like a perfect blend of comfort and style.
Guest favourite
Home in Burbank
4.83 out of 5 average rating, 23 reviews

Cozy getaway in the city.

CynthiaRating, 5 stars1 week ago
Juan was not only a great communicator but his home was beautiful and centrally located. If ever in the Chicago/Burbank area would definitely love to rent.
Top guest favourite
Home in Chicago
5 out of 5 average rating, 23 reviews

Villa Noir Chicago Victorian 7 min to downtown

EddieRating, 5 stars2 weeks ago
Great place. Great communication. Perfect for what we needed. Great house. Great neighborhood, right outside of downtown.

Private house rentals

Guest favourite
Home in Chicago
4.93 out of 5 average rating, 30 reviews

Bronzeville Home! Downtown + McCormick + U of C

CynthiaRating, 5 stars1 week ago
Great place for my family to stay! Rides to downtown, Navy Pier and Hyde Park were short and the kitchen and living room were very spacious. Henok was very kind and flexible!
Guest favourite
Home in Chicago
4.92 out of 5 average rating, 51 reviews

Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design

MohannadRating, 5 stars2 weeks ago
the house looked better than the pictures and the house was bigger than expected the heated floors were a great luxury I'd recommend to stay here but also recommend the owners 1 thing 1 the toilets need to be changed u have to wait like 5 mins in-between flushes they were very low pressured got irritating also the basement had a flood under the carpets near the pool table which made me not play pool bc I was standing in a soaked carpet which is an easy fix for future guest I'd recommend staying here if u want to be close to the city but not be in the heart of it and want to have easy parking n access to ur car
Superhost
Home in Chicago
4.75 out of 5 average rating, 24 reviews

Garden/unit/1+1/cosy

RobertRating, 5 stars2 days ago
Wonderful home close to train station. Very convenient and cozy. Would recommend!
Guest favourite
Home in Chicago
4.93 out of 5 average rating, 27 reviews

3 bd/ 2ba with Free Parking Spot by McCormick

AadhyaRating, 5 stars1 week ago
Had an amazing experience!! Host was very quick with responding on text if there were any issues too.
Superhost
Home in Gary
4.84 out of 5 average rating, 57 reviews

The Blue House: Family Retreat

AprilRating, 5 stars6 days ago
Lots of space for my family and Inwhom were visiting from out of town. The kids loved the karaoke machine and little popcorn machine. I didn’t realize 2 beds upstairs were toddler beds, but It was accommodating. Super cute.
Superhost
Home in Chicago
4.69 out of 5 average rating, 72 reviews

Captivating 3 Bed 2 Bath Washington Heights Home

SteveRating, 5 stars1 month ago
Clean & spacious home. Tameka was very responsive to any questions we had.
Superhost
Home in Gary
4.91 out of 5 average rating, 79 reviews

Laurna Dune

EusebiaRating, 5 stars2 weeks ago
We had a wonderful stay at this property, it truly felt like a home away from home. The entire place was exceptionally clean, and the kitchen and dining area were spacious and easy to move around in. Both bedrooms were spotless, and the mattresses were incredibly comfortable. If you’re looking for a quiet, private place to stay, this is the perfect choice. I would definitely stay here again! 😊
Superhost
Home in Chicago
4.69 out of 5 average rating, 128 reviews

6-Bed Family Mini-Mansion for 12 Parking & Hot Tub

AnastasiaRating, 5 stars1 month ago
I truly fell in love with this home. Spot on with the photos and descriptions. Very easy to communicate with Pam, and she offered as much assistance a needed, if needed. If you have a larger group needing accommodations this is a great space. The location was very close to the expressway and is 30 minutes from Navy Pier and downtown Chicago.

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