
Holiday rentals with a pool in Cook County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Cook County
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Cook County rentals with a pool
House rentals with a pool

Home
4.93 out of 5 average rating, 44 reviewsCozy house in Schererville
kates house was excellent and clean extremely comfortable for a work trip.

Home
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
4.55 out of 5 average rating, 42 reviewsLuxurious South Suburban Villa
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
4.81 out of 5 average rating, 36 reviews30 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.

Home
4.81 out of 5 average rating, 226 reviewsOasis , Near Beach, Hard Rock and Dunes
We enjoyed our weekend trip close to the beach!

Home
4.88 out of 5 average rating, 16 reviewsSchaumburg Oasis with a Pool and Hidden Garden
This property had exactly what I needed. It was a secluded place to get a great peace of mind. The pictures did not do justice. The host was very proactive with the snow storm that was going on. Some of the best communications and updates during my visit. I will definitely look to rent from this host again when I come back to Chicago.

Home
4.93 out of 5 average rating, 75 reviewsLarge Spanish style Home (w/inground pool)
House was lovely. I enjoyed the homes decor. Every day I woke up with something else I loved. The house had everything we needed. Only thing I wished the pool heater was working and the pillows were flat. I would definitely stay here again.
Apartment rentals with a pool

Apartment
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.

Apartment
4.95 out of 5 average rating, 88 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Very nice place, convenient location if you have students at NU. I was surprised by how firm the mattresses were, all are a really hard foam not a traditional spring mattress. A word of caution regarding parking, bring only compact cars! It was very tricky to navigate into and out of the garage and parking spot with a SUV. Other than that, great stay!

Apartment
4.96 out of 5 average rating, 100 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Mihyun was a terrific host and the place was extremely comfortable and inviting. We asked for a late check out when our plans changed and she was accommodating to the best she was able to be. The glass windows all around made it possible to watch the weather, it was very peaceful. Thank you!

Apartment
New place to stayvoco: Balcony & City View
Great stay and location. Immaculate views of the city. Close walk to the Chicago and Goodman theaters. Also great breakfast and brunch spots. And some good ole’ Chicago deep dish pizza at Giordano’s. The River Walk is about a 8 minute drive and a nice 22 minute walk. Which the walk is worth it even in the cold.

Apartment
4.95 out of 5 average rating, 78 reviewsJust remodeled apartment close to airport and mall
Great apartment. Super host. Everything was great.

Apartment
4.91 out of 5 average rating, 120 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
We loved our stay here! The apartment is clean, modern and well taken care of. The instructions for check in and check out were clear and easy. The building is nice and has an underground garage and fitness center. It is an easy walk into the center of evanston. Se would definitely return!

Apartment
4.8 out of 5 average rating, 25 reviewsLovely condo studio
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.

Apartment
4.96 out of 5 average rating, 94 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
Excellent choice for a 4-6 person group. Fantastic views. Michelle was both very responsive and accommodating to our family.
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