Vacation rentals with a pool in Chicago Loop
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Chicago Loop
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 Loop rentals with a pool
House rentals with a pool
Home in The Loop
5 out of 5 average rating, 6 reviewsLuxury Condo Downtown Chicago
Home in Forest Glen
New place to stayCity Close, Country Calm
Home in Near South Side
4.86 out of 5 average rating, 29 reviews2Bed+2Bath PentHouse in South Loop
Home in Itasca
New place to stayOceanFront Resort Studio at Garza Blanca Cancun MX
Home in Schaumburg
4.96 out of 5 average rating, 25 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Condo rentals with a pool
Condo in Downers Grove
4.92 out of 5 average rating, 59 reviewsUpscale, Washer Dryer, Smoke Free, Pet Free,
Condo in Evanston
4.95 out of 5 average rating, 84 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Condo in The Loop
4.69 out of 5 average rating, 39 reviews2BD Central Downtown Location! Spacious & Cozy
Condo in Evanston
4.96 out of 5 average rating, 94 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Condo in Elk Grove Village
4.94 out of 5 average rating, 71 reviewsJust remodeled apartment close to airport and mall
Condo in Evanston
4.91 out of 5 average rating, 117 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Condo in Uptown
4.8 out of 5 average rating, 25 reviewsLovely condo studio
Quick stats about vacation rentals with a pool in Chicago Loop
Total rentals
470 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
4.7K reviews
Family-friendly rentals
140 properties are a good fit for families
Pet-friendly rentals
290 properties allow pets
Rentals with dedicated workspaces
340 properties have a dedicated workspace
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