
Holiday rentals with a pool in West Side
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in West Side
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Popular amenities for West Side rentals with a pool
House rentals with a pool

Pardizes Suites
Lisa was the best host I've ever had. The house was amazing. Definitely #1 against every other AIR BNB I've ever stayed at before. This house was comfortable, up to date (if not ahead of its time). The atmosphere was great. The beds were comfortable. There was so much to do in that home. I honestly will do my best to stay in this home again in the future. Outstanding job Lisa. See you soon!!! Rated 10 stars.......

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.

Fully Furnished Executive Home, Lux Amenities
From the time of booking until we checked in, our host Kevin was amazing!!! He was very responsive and very accommodating. Being at this location was so peaceful and felt like a home away from home. I look forward to booking with Kevin again in the future. Highly recommended

Spacious 3 Floor Townhome
good place to stay. kid frendly. close to all activities y had planned

30 mins to CHI •3 Kings •Fireplace•W/D•Workspace
The place was absolutely beautiful. Very clean and smelled so good. The house itself was gorgeous. The outdoors area was what made us book and it looked even better in person.

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!

Relaxing Spanish style Home (w/inground pool)
Stayed here the night before my wedding with my siblings who stayed the night of the wedding. We hosted our getting ready portion here for the morning of the wedding and Olinka and Daniel were gracious enough to allow us to stay in their beautiful home. Made for gorgeous pictures and a comfortable stay both nights. Thank you!!
Apartment 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
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.

"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!

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.

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
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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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- Six Flags Great America
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park Zoo
- Wilmot Mountain Ski Resort
- Flossmoor Golf Club
- Museum of Science and Industry
- Wicker Park
- Willis Tower
- Lincoln Park
- Chicago History Museum
- Skokie Country Club
- Illinois Beach State Park
- Washington Park Zoo
- Promontory Point
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