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 The Loop
5 out of 5 average rating, 6 reviewsLuxury Condo Downtown Chicago
Home in Glen Ellyn
4.94 out of 5 average rating, 18 reviewsGlen Ellyn Home
Home in Munster
5 out of 5 average rating, 8 reviewsMunster hide away
Home in Near South Side
4.86 out of 5 average rating, 29 reviews2Bed+2Bath PentHouse in South Loop
Home in Bloomingdale
4.94 out of 5 average rating, 35 reviewsWhole House with a Hot Tub!
Home in Schaumburg
4.82 out of 5 average rating, 11 reviewsSchaumburg Oasis with a Pool and Hidden Garden
Home in Glenwood
4.79 out of 5 average rating, 53 reviewsSpacious Family Glenwood Estates Home w/ Hot Tub!
Home in Carol Stream
4.86 out of 5 average rating, 7 reviewsSpacious 4 Bed/3.5 Bath Sleeps 8+
Condo rentals with a pool
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, 84 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Condo in The Loop
4.69 out of 5 average rating, 39 reviews2BD Central Downtown Location! Spacious & Cozy
Condo in Evanston
4.96 out of 5 average rating, 94 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Condo in Lombard
4.83 out of 5 average rating, 53 reviewsSmoke & Pet Free, Washer Dryer, Fireplace, Balcony
Condo in Evanston
4.91 out of 5 average rating, 117 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Condo in Uptown
4.8 out of 5 average rating, 25 reviewsLovely condo studio
Condo in Lombard
4.91 out of 5 average rating, 44 reviewsPond View, Washer Dryer, Non Smoking Community
Quick stats about vacation rentals with a pool in Chicago
Total rentals
1.1K properties
Total number of reviews
11K reviews
Family-friendly rentals
320 properties are a good fit for families
Pet-friendly rentals
670 properties allow pets
Rentals with dedicated workspaces
780 properties have a dedicated workspace
Wifi availability
1.1K properties include access to wifi
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