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 Plainfield
4.95 out of 5 average rating, 62 reviewsLarge Spanish style Home (w/heated pool)
Aug. 5 – 12
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
May 25 – Jun. 1
Home in Chicago
4.86 out of 5 average rating, 36 reviewsLuxury Cabin in Lakeview
Jul. 7 – 12
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
Jul. 23 – 30
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Jan. 12 – 19
Home in Schaumburg
New place to stayParadise 4BR w/ Pool & Games
Aug. 5 – 12
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Jul. 14 – 21
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Nov. 23 – 30
Condo rentals with a pool
Condo in Chicago
4.75 out of 5 average rating, 145 reviewsCentral Downtown Location-Modern 2BR Condo
Jul. 3 – 10
Condo in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
Sep. 27 – Oct. 4
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Jan. 29 – Feb. 5
Condo in Chicago
4.7 out of 5 average rating, 27 reviews1 bedroom in the heart of downtown Chicago.
Jul. 7 – 14
Condo in Evanston
4.96 out of 5 average rating, 78 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Dec. 10 – 17
Condo in Evanston
4.94 out of 5 average rating, 71 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Jul. 24 – 31
Condo in Evanston
4.97 out of 5 average rating, 72 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
Jan. 29 – Feb. 5
Condo in Downers Grove
4.9 out of 5 average rating, 52 reviewsUpscale, Washer Dryer, Smoke Free, Pet Free,
May 27 – Jun. 3
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
Destinations to explore
- Downtown Chicago Vacation rentals
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- Rentals with pools United States
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