Holiday rentals with a pool in Cook County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Cook County rentals with a pool

House rentals with a pool

Guest favourite

Home

4.93 out of 5 average rating, 44 reviews

Cozy house in Schererville

DanielRating, 5 stars1 week ago
kates house was excellent and clean extremely comfortable for a work trip.
Guest favourite

Home

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

4.55 out of 5 average rating, 42 reviews

Luxurious South Suburban Villa

LanceRating, 5 stars2 weeks ago
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 reviews

30 mins to CHI* 3 Kings *Fireplace *W/D* Workspace

Demetrianna RRating, 5 stars5 months ago
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 reviews

Oasis , Near Beach, Hard Rock and Dunes

AlisonRating, 5 stars5 months ago
We enjoyed our weekend trip close to the beach!
Guest favourite

Home

4.88 out of 5 average rating, 16 reviews

Schaumburg Oasis with a Pool and Hidden Garden

BrianRating, 5 stars2 days ago
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.
Guest favourite

Home

4.93 out of 5 average rating, 75 reviews

Large Spanish style Home (w/inground pool)

DevonRating, 5 stars4 months ago
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

Guest favourite

Apartment

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 favourite

Apartment

4.95 out of 5 average rating, 88 reviews

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

MelanieRating, 5 stars2 weeks ago
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!
Guest favourite

Apartment

4.96 out of 5 average rating, 100 reviews

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

SarahRating, 5 stars1 week ago
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 stay

voco: Balcony & City View

TamonRating, 5 stars3 weeks ago
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.
Guest favourite

Apartment

4.95 out of 5 average rating, 78 reviews

Just remodeled apartment close to airport and mall

Ralf OliverRating, 5 stars2 months ago
Great apartment. Super host. Everything was great.
Guest favourite

Apartment

4.91 out of 5 average rating, 120 reviews

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

DominicRating, 5 stars2 weeks ago
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!
Superhost

Apartment

4.8 out of 5 average rating, 25 reviews

Lovely condo studio

EileenRating, 5 stars6 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

4.96 out of 5 average rating, 94 reviews

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

RichardRating, 5 stars1 week ago
Excellent choice for a 4-6 person group. Fantastic views. Michelle was both very responsive and accommodating to our family.

Destinations to explore