Vacation rentals with a pool in Chicago
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Chicago
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago rentals with a pool
House rentals with a pool
Home in Glen Ellyn
4.94 out of 5 average rating, 18 reviewsGlen Ellyn Home
Home in Munster
5 out of 5 average rating, 6 reviewsMunster hide away
Home in Plainfield
4.81 out of 5 average rating, 36 reviewsPool* 3 Kings* BBQ & Patio*Playground*Fire Table
Home in Near South Side
4.86 out of 5 average rating, 28 reviews2Bed+2Bath PentHouse in South Loop
Home in Bloomingdale
4.97 out of 5 average rating, 31 reviewsGiant Swimming Pool with Whole House!
Home in Schaumburg
4.88 out of 5 average rating, 8 reviewsParadise Garden Oasis with a Pool in Schaumburg.
Home in Glenwood
4.79 out of 5 average rating, 53 reviewsSpacious Family Glenwood Estates Home w/ Hot Tub!
Home in Itasca
New place to stayOceanFront Resort Studio at Garza Blanca Cancun MX
Condo rentals with a pool
Condo in Oak Lawn
5 out of 5 average rating, 3 reviews2flr Spacious-3bedrms 2bath with Garage Parking
Condo in Downers Grove
4.92 out of 5 average rating, 59 reviewsUpscale, Washer Dryer, Smoke Free, Pet Free,
Condo in Evanston
4.95 out of 5 average rating, 82 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Condo in Evanston
4.96 out of 5 average rating, 91 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Condo in Oak Lawn
5 out of 5 average rating, 5 reviews1Flr Spacious 3Bedrooms/2 Bath w Garage Parking
Condo in Lombard
4.83 out of 5 average rating, 52 reviewsSmoke & Pet Free, Washer Dryer, Fireplace, Balcony
Condo in Evanston
4.91 out of 5 average rating, 116 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Condo in Uptown
4.73 out of 5 average rating, 26 reviewsLovely condo studio
Quick stats about vacation rentals with a pool in Chicago
Total rentals
1.1K properties
Total number of reviews
9.2K reviews
Family-friendly rentals
320 properties are a good fit for families
Pet-friendly rentals
680 properties allow pets
Rentals with dedicated workspaces
740 properties have a dedicated workspace
Wifi availability
1.1K properties include access to wifi
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