
Holiday 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.
Holiday 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 The Loop
5 out of 5 average rating, 6 reviewsLuxury Condo Downtown Chicago

Home in Olympia Fields
4.54 out of 5 average rating, 41 reviewsLuxurious South Suburban Villa

Home in Lockport
4.67 out of 5 average rating, 3 reviewsHidden GEM OASIS in Chicagoland

Home in Schaumburg
4.87 out of 5 average rating, 15 reviewsSchaumburg Oasis with a Pool and Hidden Garden

Home in Austin
New place to stay4Bed GemW/Pool for8 Near ORD/MDW

Home in Glenwood
4.8 out of 5 average rating, 55 reviewsSpacious Family Glenwood Estates Home w/ Hot Tub!
Apartment rentals with a pool

Apartment in Downers Grove
4.92 out of 5 average rating, 61 reviewsUpscale, Washer Dryer, Smoke Free, Pet Free,

Apartment in Evanston
4.95 out of 5 average rating, 87 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

Apartment in Evanston
4.96 out of 5 average rating, 99 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Apartment in The Loop
New place to stayvoco: Balcony & City View

Apartment in Elk Grove Village
4.95 out of 5 average rating, 78 reviewsJust remodeled apartment close to airport and mall

Apartment in Evanston
4.91 out of 5 average rating, 120 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba

Apartment in Lombard
4.91 out of 5 average rating, 45 reviewsPond View, Washer Dryer, Non Smoking Community
Quick stats about holiday rentals with a pool in Chicago
Total rentals
1.1K properties
Nightly prices starting at
$13 SGD before taxes and fees
Total number of reviews
12K reviews
Family-friendly rentals
330 properties are a good fit for families
Pet-friendly rentals
740 properties allow pets
Rentals with dedicated workspaces
800 properties have a dedicated workspace
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