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 Schaumburg
5.0 out of 5 average rating, 3 reviewsParadise 4BR w/ Pool & Games
Home in Chicago
4.87 out of 5 average rating, 38 reviewsLuxury Cabin in Lakeview
Home in Glen Ellyn
4.94 out of 5 average rating, 17 reviewsGlen Ellyn Home
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Home in Gary
4.82 out of 5 average rating, 214 reviewsOasis , Near Beach, Hard Rock and Dunes
Home in New Lenox
4.74 out of 5 average rating, 35 reviewsCheerful home. Heated pool, Hot tub!
Condo rentals with a pool
Condo in Chicago
4.74 out of 5 average rating, 148 reviewsCentral Downtown Location-Modern 2BR Condo
Condo in Downers Grove
4.88 out of 5 average rating, 52 reviewsUpscale, Smoke and Pet Free, Washer Dryer, Balcony
Condo in Chicago
4.78 out of 5 average rating, 18 reviewsLovely condo studio
Condo in Chicago
4.68 out of 5 average rating, 28 reviews1 bedroom in the heart of downtown Chicago.
Condo in Chicago
4.0 out of 5 average rating, 9 reviews30 E. Huron #2305 Private Residence
Condo in Evanston
4.94 out of 5 average rating, 71 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
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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