Vacation rentals with a pool in Cook County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Cook County
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 Cook County rentals with a pool
House rentals with a pool
Home in Plainfield
4.95 out of 5 average rating, 62 reviewsSpanish style Home (w/heated pool)
Sep 17 – 24
Home in Schaumburg
5.0 out of 5 average rating, 3 reviewsParadise 4BR w/ Pool & Games
Nov 21 – 28
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Nov 19 – 26
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
Jul 23 – 30
Home in Chicago
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
Jul 7 – 14
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Jul 22 – 29
Home in Gary
4.82 out of 5 average rating, 213 reviewsOasis , Near Beach, Hard Rock and Dunes
Nov 20 – 27
Home in Schererville
5.0 out of 5 average rating, 4 reviewsCozy house in Schererville
Sep 5 – 12
Condo rentals with a pool
Condo in Chicago
4.74 out of 5 average rating, 147 reviewsCentral Downtown Location-Modern 2BR Condo
Jul 4 – 11
Condo in Portage
5.0 out of 5 average rating, 53 reviewsLuxury Waterfront 2 Bedroom Condo by Lake Michigan
Sep 4 – 11
Condo in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
Dec 31 – Jan 7
Condo in Portage
4.91 out of 5 average rating, 23 reviewsSerenity on the Shores
Mar 18 – 25
Condo in Portage
5.0 out of 5 average rating, 6 reviewsHarbor Haven Hideaway
Jan 5 – 12
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Oct 15 – 22
Condo in Chicago
4.7 out of 5 average rating, 27 reviews1 bedroom in the heart of downtown Chicago.
Jul 21 – 28
Condo in Portage
New place to stayDuneside Haven
Sep 3 – 10
Destinations to explore
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