Vacation rentals with a pool in North Side
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in North Side
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 North Side rentals with a pool
House rentals with a pool
Home in Chicago
4.86 out of 5 average rating, 36 reviewsLuxury Cabin in Lakeview
Jul. 7 – 12
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
May 25 – Jun. 1
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
Jul. 23 – 30
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Jan. 12 – 19
Home in Schaumburg
New place to stayParadise 4BR w/ Pool & Games
Aug. 5 – 12
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Nov. 23 – 30
Home in Carol Stream
4.55 out of 5 average rating, 20 reviewsAmazing Summer Pool Awaits You!
Nov. 3 – 10
Home in Bartlett
5.0 out of 5 average rating, 4 reviewsFully Furnished Executive Home, Lux Amenities
Dec. 8 – 15
Condo rentals with a pool
Condo in Chicago
4.75 out of 5 average rating, 145 reviewsCentral Downtown Location-Modern 2BR Condo
Jul. 3 – 10
Condo in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
Nov. 21 – 28
Condo in Downers Grove
4.9 out of 5 average rating, 52 reviewsUpscale, Washer Dryer, Smoke Free, Pet Free,
May 28 – Jun. 4
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Jan. 29 – Feb. 5
Condo in Chicago
4.7 out of 5 average rating, 27 reviews1 bedroom in the heart of downtown Chicago.
Jul. 7 – 14
Condo in Evanston
4.96 out of 5 average rating, 78 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Dec. 10 – 17
Condo in Evanston
4.97 out of 5 average rating, 72 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
Jan. 29 – Feb. 5
Condo in Evanston
4.94 out of 5 average rating, 71 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Jul. 24 – 31
Destinations to explore
- Downtown Chicago Vacation rentals
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- Rentals with pools United States
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