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 Niles
5.0 out of 5 average rating, 12 reviewsLuxury Modern House Epic Master Bath & Pool Table
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Home in Skokie
Skokie town home
Home in Chicago
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
Condo rentals with a pool
Condo in Evanston
4.91 out of 5 average rating, 102 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Condo in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
Condo in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
Condo in Chicago
4.7 out of 5 average rating, 27 reviews1 bedroom in the heart of downtown Chicago.
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Condo in Evanston
4.95 out of 5 average rating, 87 reviewsHarmony of Evanston 1 BDR Exec Suite w/pool & Gym
Condo in Evanston
4.97 out of 5 average rating, 73 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
Condo in Evanston
4.94 out of 5 average rating, 71 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Quick stats about vacation rentals with a pool in Chicago Loop
Total rentals
480 properties
Rentals with dedicated workspaces
330 properties have a dedicated workspace
Pet-friendly rentals
280 properties allow pets
Family-friendly rentals
150 properties are a good fit for families
Total number of reviews
3.9K reviews
Nightly prices starting at
$50 before taxes and fees
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