Vacation rentals with a pool in Near North Side, Chicago

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Popular amenities for Near North Side, Chicago rentals with a pool

House rentals with a pool

Guest favorite

Home in The Loop

5 out of 5 average rating, 6 reviews

Luxury Condo Downtown Chicago

CarsonRating, 5 stars15 months ago
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 reviews

Hidden GEM OASIS in Chicagoland

RaymondRating, 5 stars2 months ago
There were a few small issues we noticed upon arrival. Nico jumped right on it and corrected them for us that day!
Guest favorite

Home in Schaumburg

4.87 out of 5 average rating, 15 reviews

Schaumburg Oasis with a Pool and Hidden Garden

LisaRating, 5 stars1 month ago
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 reviews

Spacious Family Glenwood Estates Home w/ Hot Tub!

JosiahRating, 5 stars2 months ago
It was a wonderful experience staying at evolves home. It was very clean, and spacious enough for all my siblings to be comfortable.
Guest favorite

Home in Schaumburg

4.95 out of 5 average rating, 20 reviews

Paradise 4BR w/ Pool & Games

JasonRating, 5 stars5 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

Guest favorite

Condo in Downers Grove

4.92 out of 5 average rating, 61 reviews

Upscale, Washer Dryer, Smoke Free, Pet Free,

NormaRating, 5 stars1 month 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 favorite

Condo in Evanston

4.95 out of 5 average rating, 87 reviews

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

AdrielleRating, 5 stars2 months ago
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!
Guest favorite

Condo in Evanston

4.96 out of 5 average rating, 98 reviews

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

MichelleRating, 5 stars1 month ago
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!
Guest favorite

Condo in Elk Grove Village

4.95 out of 5 average rating, 78 reviews

Just remodeled apartment close to airport and mall

Ralf OliverRating, 5 stars1 month ago
Great apartment. Super host. Everything was great.
Guest favorite

Condo in Evanston

4.91 out of 5 average rating, 119 reviews

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

JosephRating, 5 stars2 months ago
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 reviews

Pond View, Washer Dryer, Non Smoking Community

CalebRating, 5 stars3 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.
Guest favorite

Condo in Evanston

4.96 out of 5 average rating, 93 reviews

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

JoshRating, 5 stars1 month ago
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 reviews

Upscale, Smoke and Pet Free, Washer Dryer, Balcony

Lee AnnRating, 5 stars5 months ago
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

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. Near North Side
  7. Rentals with pools