Vacation rentals with a pool in Near North Side, Chicago
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Near North Side, Chicago
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 Near North Side, Chicago rentals with a pool
House rentals with a pool
Home in Chicago
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
Jul 7 – 14
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Jan 13 – 20
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
Jul 23 – 30
Home in Schaumburg
5.0 out of 5 average rating, 3 reviewsParadise 4BR w/ Pool & Games
Aug 13 – 20
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Nov 7 – 14
Home in Carol Stream
4.55 out of 5 average rating, 20 reviewsAmazing Summer Pool Awaits You!
Dec 7 – 14
Home in Glenwood
4.84 out of 5 average rating, 37 reviewsSpacious Family Glenwood Estates Home w/ Hot Tub!
Aug 6 – 13
Home in Tinley Park
4.8 out of 5 average rating, 5 reviewsPerfect safe stay
Jan 23 – 30
Condo rentals with a pool
Condo in Chicago
4.74 out of 5 average rating, 146 reviewsCentral Downtown Location-Modern 2BR Condo
Jul 10 – 17
Condo in Lisle
4.95 out of 5 average rating, 42 reviewsPeaceful Condo in Lisle, Illinois
Dec 1 – 8
Condo in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
Sep 16 – 23
Condo in Downers Grove
4.88 out of 5 average rating, 52 reviewsUpscale, Smoke and Pet Free, Washer Dryer, Balcony
Oct 20 – 27
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Sep 16 – 23
Condo in Chicago
4.7 out of 5 average rating, 27 reviews1 bedroom in the heart of downtown Chicago.
Jul 6 – 13
Condo in Evanston
4.94 out of 5 average rating, 71 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Nov 18 – 25
Condo in Evanston
4.97 out of 5 average rating, 73 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
Oct 21 – 28
Quick stats about vacation rentals with a pool in Near North Side, Chicago
Total rentals
720 properties
Wifi availability
720 properties include access to wifi
Rentals with dedicated workspaces
500 properties have a dedicated workspace
Pet-friendly rentals
470 properties allow pets
Family-friendly rentals
200 properties are a good fit for families
Total number of reviews
5.8K reviews
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