Vacation rentals with a pool in South Side

Find and book unique homes with a pool on Airbnb

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Popular amenities for South Side rentals with a pool

House rentals with a pool

Home in Glen Ellyn
4.8 out of 5 average rating, 5 reviews

Pardizes Suites

FernandaRating, 5 stars1 week ago
Really nice and spacious place. Everything was clean and comfy.
Guest favourite
Home in Glen Ellyn
4.95 out of 5 average rating, 20 reviews

Glen Ellyn Home

TimothyRating, 5 stars4 months ago
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.
Home in Olympia Fields
4.56 out of 5 average rating, 43 reviews

Luxurious South Suburban Villa

LanceRating, 5 stars2 months ago
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.
Home in Lockport
4.63 out of 5 average rating, 8 reviews

Hidden GEM OASIS in Chicagoland

Raymond BrianRating, 5 stars3 weeks ago
Excellent host! Fantastic property!
Home in Schaumburg
4.75 out of 5 average rating, 8 reviews

Spacious 3 Floor Townhome

AndresRating, 5 stars1 day ago
My spouse and I couldn't of had a better weekend without Alex's listing! Everything was as Alex had described it in the post. It was close to restaurants, grocery stores and entertainment needs. Alex made it easy check in and check out. We would definitely recommend this place to any couple or small family.
Guest favourite
Home in Schaumburg
4.91 out of 5 average rating, 22 reviews

Schaumburg Oasis with a Pool and Hidden Garden

GotimukulRating, 5 stars3 weeks ago
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!
Home in Glenwood
4.8 out of 5 average rating, 56 reviews

Spacious Family Glenwood Estates Home w/ Hot Tub!

Nicole And ArnoRating, 5 stars1 month ago
Loved this Airbnb! Didn’t want to leave.
Guest favourite
Home in Schaumburg
4.95 out of 5 average rating, 20 reviews

Paradise 4BR w/ Pool & Games

JasonRating, 5 stars8 months ago
We really enjoyed our stay at this beautiful home. It is close to everything. The place is clean and very organized. Lily and Nathan has been wonderful and very responsive and communicated well with us. I definitely recommend this place when you visit Schaumburg. Thank you guys for everything.

Condo rentals with a pool

Condo in Downers Grove
4.92 out of 5 average rating, 62 reviews

Upscale, Washer Dryer, Smoke Free, Pet Free,

NormaRating, 5 stars3 months ago
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.
Superhost
Condo in Evanston
4.96 out of 5 average rating, 94 reviews

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

PeteRating, 5 stars2 days ago
This condo is well appointed and stocked with coffee, creamer and seasonings. The building has a nice common area with fancy coffees and a decent work out room. We love the location near downtown Evanston and the public transportation to Chicago. We’ve stayed here many times and plan to stay here for all our Chicago visits.
Superhost
Condo in Evanston
4.96 out of 5 average rating, 104 reviews

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

JasonRating, 5 stars1 week ago
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!
Condo in Chicago
4.33 out of 5 average rating, 9 reviews

30 E. Huron #2603 Private Residence

Diego HernanRating, 5 stars23 months ago
Incredible experience. Kevin was very nice and helped us with everything. I would go back again to this amazing apartment and great location.
Condo in Elk Grove Village
4.94 out of 5 average rating, 85 reviews

Just remodeled apartment close to airport and mall

MeagRating, 5 stars1 month ago
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! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️
Superhost
Condo in Evanston
4.91 out of 5 average rating, 124 reviews

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

NinaRating, 5 stars1 month ago
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!
Condo in Lombard
4.91 out of 5 average rating, 45 reviews

Pond View, Washer Dryer, Non Smoking Community

CalebRating, 5 stars6 months ago
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.
Superhost
Condo in Evanston
4.96 out of 5 average rating, 97 reviews

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

JohnRating, 5 stars1 month ago
We really enjoyed staying at Michelle's place. It was a perfect home away from home while visiting Northwestern University. The area had many cafes and restaurants. The place was spacious with three bedrooms and two bathrooms. The primary suite had a very firm mattress. But this did not bother us at all. The kitchen was well stocked with pots, pans, glasses, plates and utensils. There's a coffee maker and we were able to try some local coffees in the area. We enjoyed having family dinners on the bar style, raised table and stools. The view of the sunset from the balcony was amazing each night with purples, pinks and trees - fantastic views of Evanston. The place is great for watching movies with a long couch lounger, cozy seats and cup holders! The area is a perfect blend of city and nature with Lake Michigan nearby. We will definitely be back.

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