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
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
9–16 Jan
Home in Chicago
4.86 out of 5 average rating, 36 reviewsLuxury Cabin in Lakeview
7–12 Jul
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
5–12 May
Home in Schaumburg
New place to stayParadise 4BR w/ Pool & Games
25 Jun – 2 Jul
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
5–12 Jul
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
6–13 Nov
Home in New Lenox
4.74 out of 5 average rating, 34 reviewsCheerful home. Heated pool, Hot tub!
21–28 Jun
Home in Olympia Fields
4.58 out of 5 average rating, 31 reviewsLuxurious South Suburban Villa
16–23 Sep
Apartment rentals with a pool
Apartment in Chicago
4.75 out of 5 average rating, 144 reviewsCentral Downtown Location-Modern 2BR Condo
9–16 Jul
Apartment in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
3–10 Jan
Apartment in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
8–15 Sep
Apartment in Chicago
4.7 out of 5 average rating, 27 reviews1 bedroom in the heart of downtown Chicago.
10–17 Jul
Apartment in Evanston
4.96 out of 5 average rating, 78 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
10–17 Dec
Apartment in Evanston
4.94 out of 5 average rating, 69 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
24–31 Jul
Apartment in Evanston
4.97 out of 5 average rating, 71 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
29 Jan – 5 Feb
Apartment in Downers Grove
4.9 out of 5 average rating, 52 reviewsUpscale, Washer Dryer, Smoke Free, Pet Free,
25 May – 1 Jun
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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