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 Glen Ellyn
4.74 out of 5 average rating, 19 reviewsGlen Ellyn Home
Home in Near South Side
4.85 out of 5 average rating, 26 reviews2Bed+2Bath PentHouse in South Loop
Home in Bloomingdale
4.96 out of 5 average rating, 27 reviewsGiant Swimming Pool with Whole House!
Home in Itasca
New place to stayOceanFront Resort Studio at Garza Blanca Cancun MX
Home in Skokie
Skokie town home
Home in Bensenville
5 out of 5 average rating, 10 reviewsNew! Arcade+Sauna+Slots+Karaoke+more by O’Hare
Home in Schaumburg
4.96 out of 5 average rating, 24 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Bridgeport
Sweet Home Chicago (house) - free parking, pool
Condo rentals with a pool
Condo in Oak Lawn
2flr 3bedrms 2bath w Garage Parking
Condo in Evanston
4.95 out of 5 average rating, 88 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Condo in Oak Lawn
5 out of 5 average rating, 4 reviews1Flr 3Bedrooms/2 Bath with Garage Parking
Condo in Lombard
4.82 out of 5 average rating, 50 reviewsSmoke & Pet Free, Washer Dryer, Fireplace, Balcony
Condo in Elk Grove Village
4.94 out of 5 average rating, 68 reviewsJust remodeled apartment close to airport and mall
Condo in Evanston
4.9 out of 5 average rating, 115 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Condo in Uptown
4.73 out of 5 average rating, 26 reviewsLovely condo studio
Condo in Lombard
4.93 out of 5 average rating, 42 reviewsPond View, Washer Dryer, Non Smoking Community
Quick stats about vacation rentals with a pool in Chicago Loop
Total rentals
470 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
4.1K reviews
Family-friendly rentals
150 properties are a good fit for families
Pet-friendly rentals
280 properties allow pets
Rentals with dedicated workspaces
320 properties have a dedicated workspace
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