Holiday rentals with a pool in North Side

Find and book unique homes with a pool on Airbnb

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Popular amenities for North Side rentals with a pool

House rentals with a pool

Home in Evanston
4.89 out of 5 average rating, 44 reviews

Beautiful Historic Colonial

AlexisRating, 5 stars4 months ago
Great weekend for our 25th reunion. We were 8 adults. Enjoyed the spacious dining room. Kitchen was well stocked. We hope to spend our next reunion weekend back at the house!
Home in Glen Ellyn
4.67 out of 5 average rating, 3 reviews

Pardizes Suites

AlineRating, 5 stars2 weeks ago
Loved everything about the place; spacious enough (big rooms for all of us, we were 5) so cozy and pretty, quiet neighborhood, Lisa is responsive and the amenities!!!🥰 I definitely recommend and I’ll stay here every time my friends and I come to Chicago :)
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.
Superhost
Home in Schaumburg
4.9 out of 5 average rating, 21 reviews

Schaumburg Oasis with a Pool and Hidden Garden

AlyssaRating, 5 stars4 days ago
This home is absolutely amazing! It has tons of space and so many cool things that weren’t even listed in the description. Marzena is an amazing host and we will definitely be back. The backyard is beautiful as well!
Superhost
Home in Lake Forest
4.9 out of 5 average rating, 63 reviews

Beautiful 137 Year Old Farm Home (3night min)

MaribethRating, 5 stars7 months ago
Beautiful and eclectic home. It was perfect for our group of girls visiting from all over the U.S to attend our HS Reunion. Plenty of lovely spaces to gather or a private, quiet nook to read or rest. The pool was wonderful. Beds were super comfortable. Kitchen was large enough and well stocked to prepare meals. Andy was very responsive with any issues or questions. Highly recommend!
Superhost
Home in Schaumburg
4.95 out of 5 average rating, 20 reviews

Paradise 4BR w/ Pool & Games

JasonRating, 5 stars7 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.
Superhost
Home in West Chicago
4.93 out of 5 average rating, 14 reviews

Cozy & Relax Escape

SamRating, 5 stars4 months ago
I had a great stay at Kisha’s cozy basement apartment. It was nice to have my own space and have a kitchenette to prepare some easy meals. Kisha was friendly and communicative. I met her sweet cat Giggles as well!

Apartment rentals with a pool

Guest favourite
Apartment in Downers Grove
4.92 out of 5 average rating, 61 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.
Guest favourite
Apartment in Evanston
4.96 out of 5 average rating, 91 reviews

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

TimRating, 5 stars1 month ago
Competitive rates compared to hotel choices with well stocked kitchen which included coffee and tea, above average water pressure for your shower, and an indoor parking spot just steps from the elevator (no extra charge). Comfortable clean and surprisingly quiet with responsive hosts. Highly recommended!
Guest favourite
Apartment in Evanston
4.96 out of 5 average rating, 102 reviews

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

SergeRating, 5 stars3 weeks ago
Gorgeous apartment with stunning views, stay here if you can!
Apartment in Chicago
4.2 out of 5 average rating, 5 reviews

voco: Balcony & City View

GavynRating, 5 stars3 weeks ago
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.
Guest favourite
Apartment in Elk Grove Village
4.94 out of 5 average rating, 83 reviews

Just remodeled apartment close to airport and mall

MarcyRating, 5 stars2 weeks ago
I stayed here because I was going to a concert nearby in the Allstate Arena. The place was just as pictured and was very clean! Instructions on how to get into the building were very clear and easy to follow. The host was also very responsive and kind! I would book here again if I am in the area!
Guest favourite
Apartment in Evanston
4.91 out of 5 average rating, 124 reviews

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

NinaRating, 5 stars1 week 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!
Apartment in Chicago
4.8 out of 5 average rating, 25 reviews

Lovely condo studio

EileenRating, 5 stars8 months ago
Great studio apartment with very friendly neighbors in a great neighborhood with amazing restaurants. Walking distance to Andersonville, a neighborhood with antique book stores, oddity shops, enough to keep you busy all day. Perfect location. I will stay there again.
Guest favourite
Apartment in Evanston
4.96 out of 5 average rating, 95 reviews

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

JulieRating, 5 stars2 weeks ago
Perfectly clean and easy to fit 7 adults for a weekend. Towels, toiletries, etc all adequate. Mihyun was great communicator. Kitchen could use MORE WINE GLASSES and more water glasses. There were only 7 glasses total so every time I used a glass I had to wash it for the next person. Not a deal breaker but was a bummer since we are all wine drinkers and had to, god forbid, drink red wine out of a "cheap" champagne glass! No other complaints, though, so would totally book again for a visit to Northwestern.

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