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 Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Chicago
4.87 out of 5 average rating, 39 reviewsLuxury Cabin in Lakeview
Home in Schaumburg
4.43 out of 5 average rating, 7 reviewsParadise 4BR w/ Pool & Games
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Home in New Lenox
4.75 out of 5 average rating, 36 reviewsCheerful home. Heated pool, Hot tub!
Home in Plainfield
4.89 out of 5 average rating, 27 reviewsPool* 3 King beds* Grill & Patio* 30mi to Chicago
Home in Chicago
4.83 out of 5 average rating, 18 reviews2Bed+2Bath PentHouse in South Loop
Home in Carol Stream
4.55 out of 5 average rating, 20 reviewsAmazing Summer Pool Awaits You!
Condo rentals with a pool
Condo in Chicago
4.75 out of 5 average rating, 150 reviewsCentral Downtown Location-Modern 2BR Condo
Condo in Lombard
4.97 out of 5 average rating, 37 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
Condo in Chicago
4.79 out of 5 average rating, 19 reviewsLovely condo studio
Condo in Chicago
4.68 out of 5 average rating, 28 reviews1 bedroom in the heart of downtown Chicago.
Condo in Evanston
4.94 out of 5 average rating, 72 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Condo in Evanston
4.95 out of 5 average rating, 79 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Condo in Evanston
4.97 out of 5 average rating, 75 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
Condo in Lombard
4.71 out of 5 average rating, 24 reviewsSmoke Free Community, Pet Free Unit, Washer Dryer
Quick stats about vacation rentals with a pool in Chicago
Total rentals
1.1K properties
Wifi availability
1.1K properties include access to wifi
Rentals with dedicated workspaces
740 properties have a dedicated workspace
Pet-friendly rentals
700 properties allow pets
Family-friendly rentals
300 properties are a good fit for families
Total number of reviews
9.2K reviews
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