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Holiday rentals with a pool in Downtown Chicago
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Downtown 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 Downtown Chicago rentals with a pool
House rentals with a pool
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Home in Schaumburg
4.92 out of 5 average rating, 13 reviewsParadise 4BR w/ Pool & Games
![](https://a0.muscache.com/im/pictures/hosting/Hosting-1152484478779189306/original/4a3b2311-84f1-4d00-b28a-a60b1182f5fe.jpeg?im_w=720)
Home in Bloomingdale
4.93 out of 5 average rating, 14 reviewsGiant Swimming Pool with Whole House!
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Home in Schaumburg
4.95 out of 5 average rating, 20 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
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Home in Chicago
4.85 out of 5 average rating, 46 reviewsLuxury Cabin in Lakeview
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Home in Chicago
4.82 out of 5 average rating, 22 reviews2Bed+2Bath PentHouse in South Loop
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Home in Bensenville
5 out of 5 average rating, 3 reviewsNew! Bensenville home by O’Hare-Arcade/Sauna/Slots
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Home in Riverwoods
Riverwoods Nature Retreat
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-1178418124094019812/original/c8d99f6f-b739-4b38-a938-d85b52c0d927.jpeg?im_w=720)
Home in Evanston
New place to stay1/2 mile to NU, 5min walk to Lake, Swim Spa pool
Apartment rentals with a pool
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Apartment in Chicago
4.74 out of 5 average rating, 23 reviewsLovely condo studio
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Apartment in Elk Grove Village
4.94 out of 5 average rating, 66 reviewsJust remodeled apartment close to airport and mall
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Apartment in Lombard
4.95 out of 5 average rating, 39 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
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Apartment in Chicago
4.72 out of 5 average rating, 32 reviews1 bedroom in the heart of downtown Chicago.
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Apartment in Evanston
4.91 out of 5 average rating, 110 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
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Apartment in Downers Grove
4.88 out of 5 average rating, 52 reviewsUpscale, Smoke and Pet Free, Washer Dryer, Balcony
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Apartment in Lombard
4.81 out of 5 average rating, 48 reviewsSmoke & Pet Free, Washer Dryer, Fireplace, Balcony
![](https://a0.muscache.com/im/pictures/miso/Hosting-557121615351527525/original/a1f25861-e370-46e3-8b57-4beeef1a0bf4.jpeg?im_w=720)
Apartment in Evanston
4.96 out of 5 average rating, 80 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
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