
Vacation rentals with a pool in South Side
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in South Side
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for South Side rentals with a pool
House rentals with a pool

Pardizes Suites
Really nice and spacious place. Everything was clean and comfy.

Cozy house in Schererville
Kate’s place was exactly what I expected. Pristine condition and spotless. Kate accommodated my early arrival which was greatly appreciated. I would 100% book this place again. Highly recommend her place to anyone in the area for a weekend or just to get away from the city. Thank you again for your attention on such a short notice on my booking.

Glen Ellyn Home
The property was very nice. It was well maintained and our family with our grandson were very comfortable. If we were to have a negative comment is that the heat distribution was not even throughout the home. The upstairs where the three bedrooms were located was very warm and the kitchen, living room and family were quite chilly. However, this did not impede us having a comfortable stay.

Luxurious South Suburban Villa
My team thanks you for your comfortable home, it is what the crew needs after a day working outside on a large solar field array. Whenever on an extended out of town work trip we like to stay at an Airbnb, a much better value than several rooms at hotels. Your home was roomy & comfortable, we enjoyed our stay and thank you for being a great host.

Spacious 3 Floor Townhome
This spot is awesome. Close to the mall and lots of places to eat and things to do. Very spacious tri level. Free Parking on premises. Lots of room for people to sleep very spacious. Comfy couches. The bed I had was great. Our venue was very close for the event we attended we will be back!

Oasis , Near Beach, Hard Rock and Dunes
We enjoyed our weekend trip close to the beach!

Schaumburg Oasis with a Pool and Hidden Garden
had such a wonderful stay! The place was exactly as described—clean, cozy, and beautifully maintained. The host was incredibly kind and responsive, making the whole experience smooth and stress-free. Would definitely stay here again and highly recommend it to anyone looking for a comfortable and welcoming place to stay!

Little Pink House Downtown
The Little Pink House greatly exceeded our expectations. Suzanna was a wonderful host who went above and beyond to make sure our stay went smoothly. We were in town for a wedding and had an infant with us and the provided amenities made it feel like home. We would absolutely love to stay again if we get the chance.
Condo rentals with a pool

Upscale, Washer Dryer, Smoke Free, Pet Free,
My husband and I stayed here over the holidays. The apartment was pretty well appointed, clean and is in a good location- centrally located for our purposes of being near family and close enough to the expressway to get to the city.

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Really great place with lots to do nearby!

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Our stay in Evanston was great! The apartment is close to all of downtown Evanston, the Metra, and the L. Also easy access to NU. Everything was just as it says and the free underground parking is a HUGE plus!

voco: Balcony & City View
Overall very nice place for the price. Only disappointment was I got to the location listed on the air bnb listing and the actual location was 3 to 4 blocks away which I was a bit upset with. It is closer to the Chicago station on the redline than it is to the river where the listing states. Host was very responsive and allowed me to check out late to avoid waiting around at the airport for a long time.

30 E. Huron #2603 Private Residence
Incredible experience. Kevin was very nice and helped us with everything. I would go back again to this amazing apartment and great location.

Just remodeled apartment close to airport and mall
I am incredibly particular with places I stay. This place was simple, very clean, had everything you would need to be comfortable. Bed was great! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba
We had a great stay at Michelle’s “Heart of Evanston.” I loved the indoor garage parking option with easy in and out. If you have a large vehicle /SUV, maneuvering in and out of the spot may be challenging depending if the spot over is occupied. We have a mid-size SUV and had no issues. The room was easily accessed from the garage and we had no issues getting in. The place was clean and well organized. I loved that it smelled clean and also had a faint hint of bleach in the bathroom. It was a little warm in the bedrooms at night but we used the air conditioning to bring the temperature down. Town is very walkable and we enjoyed the local restaurants (Taco Diablo, Bat 17, Bennison’s bakery). We found the town to be very quiet - almost too quiet for what we expected but after our visit to Northwestern found out it was spring break for the students. Michelle was available for any questions and always replied promptly. We had a great stay and would stay again!

Pond View, Washer Dryer, Non Smoking Community
I stayed here while traveling for work. It was comfortable and cozy. This is a perfect place to choose for extended stays. Great location, I would recommend.
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Humboldt Park
- Six Flags Great America
- Museum of Science and Industry
- Chicago History Museum
- Lincoln Park Zoo
- The Field Museum
- 875 North Michigan Avenue
- Wicker Park
- Willis Tower
- Skokie Country Club
- Garfield Park Conservatory
- Lincoln Park
- Chicago Cultural Center
- Promontory Point
- Odyssey Fun World
- Flossmoor Golf Club
- Moraine Hills State Park