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 Schaumburg
Schaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Lincoln Park
Luxury Cabin in Lakeview
Home in Glen Ellyn
Glen Ellyn Home
Home in Schaumburg
Paradise 4BR w/ Pool & Games
Home in Chicago
2Bed+2Bath PentHouse in South Loop
Home in Carol Stream
Amazing Summer Pool Awaits You!
Home in Bloomingdale
Whole House in Bloomingdale, IL
Home in Olympia Fields
Luxurious South Suburban Villa
Apartment rentals with a pool
Apartment in The Loop
Central Downtown Location-Modern 2BR Condo
Apartment in Lombard
Pond View, Washer Dryer, Non Smoking, Pet Free
Apartment in Uptown
Lovely condo studio
Apartment in Near North Side
1 bedroom in the heart of downtown Chicago.
Apartment in Evanston
"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Apartment in Evanston
"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Apartment in Lombard
Pond View, Washer Dryer, Non Smoking Community
Apartment in Lombard
Smoke Free Community, Pet Free Unit, Washer Dryer
Quick stats about holiday 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 Holiday rentals
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- Rentals with pools United States
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