
Vacation rentals with a pool in Near North Side, Chicago
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Near North Side, Chicago
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 Near North Side, Chicago rentals with a pool
House rentals with a pool

Home in The Loop
5 out of 5 average rating, 6 reviewsLuxury Condo Downtown Chicago
Paras was an extremely friendly host. He provided a long list of recommendations and made sure we were aware he was only a message or call away.

Home in Lockport
4.67 out of 5 average rating, 3 reviewsHidden GEM OASIS in Chicagoland
There were a few small issues we noticed upon arrival. Nico jumped right on it and corrected them for us that day!

Home in Schaumburg
4.87 out of 5 average rating, 15 reviewsSchaumburg Oasis with a Pool and Hidden Garden
Marzena’s place was great…again. This is my second time renting from her. The place is spotless and she is awesome with her response time. So easy to deal with. I highly recommend and will stay there again Thanks Marzena!!!

Home in Glenwood
4.8 out of 5 average rating, 55 reviewsSpacious Family Glenwood Estates Home w/ Hot Tub!
It was a wonderful experience staying at evolves home. It was very clean, and spacious enough for all my siblings to be comfortable.

Home in Schaumburg
4.95 out of 5 average rating, 20 reviewsParadise 4BR w/ Pool & Games
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, 61 reviewsUpscale, 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.

Condo in Evanston
4.95 out of 5 average rating, 87 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
A place to just rest your head after a busy day. Nice bed and sheets. Washer and dryer, indoor heated parking helpful added bonuses. Parking felt tight but in truth fit my rental Chevy Equinox just right!

Condo in Evanston
4.96 out of 5 average rating, 98 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Our family fully enjoyed Michelle’s condo in ETOWN! We came back to visit friends over the holiday and the central location was ideal, dedicated garage parking gave us ease to come/go without searching for street level parking. The condo was spotless, amazing view from top floor, fully stocked kitchen and a great split layout with bedrooms allowing privacy (W/D also a bonus to pack light). Look forward to our return in summer! Highly recommend, very comfortable stay. Thanks again for the everything!

Condo in Elk Grove Village
4.95 out of 5 average rating, 78 reviewsJust remodeled apartment close to airport and mall
Great apartment. Super host. Everything was great.

Condo in Evanston
4.91 out of 5 average rating, 119 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Great place, very clean and accessible. Workout room was a plus! Enjoyed a memorable Thanksgiving dinner with my Northwestern clan!

Condo in Lombard
4.91 out of 5 average rating, 45 reviewsPond 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.

Condo in Evanston
4.96 out of 5 average rating, 93 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
This was a holiday trip to visit family, and this was a great option for my wife and I plus my kids and my parents. We had enough space, comfortable beds, and a well-equipped kitchen as well. Michelle was very communicative and everything was as expected. We appreciated the location - lots of things to walk to, and easy access to CTA and Metra train stations.

Condo in Downers Grove
4.87 out of 5 average rating, 54 reviewsUpscale, Smoke and Pet Free, Washer Dryer, Balcony
I have stayed at one of Briana’s places numerous times. They never disappoint. She is a great host and always responsive if I ever need anything. This condo is very clean quiet, and cozy. I highly recommend.
Quick stats about vacation rentals with a pool in Near North Side, Chicago
Total rentals
700 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
6.7K reviews
Family-friendly rentals
210 properties are a good fit for families
Pet-friendly rentals
510 properties allow pets
Rentals with dedicated workspaces
520 properties have a dedicated workspace
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