Holiday 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.
Holiday 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, 37 reviewsLuxury Cabin in Lakeview
7–14 Jul
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
8–15 Dec
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
23–30 Jul
Home in Schaumburg
New place to stayParadise 4BR w/ Pool & Games
30 Nov – 7 Dec
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
19–26 Jan
Home in Carol Stream
4.55 out of 5 average rating, 20 reviewsAmazing Summer Pool Awaits You!
31 Dec – 7 Jan
Home in Bartlett
5.0 out of 5 average rating, 4 reviewsFully Furnished Executive Home, Lux Amenities
28 Mar – 4 Apr
Home in Plainfield
4.89 out of 5 average rating, 27 reviewsPool* King beds* Grill & Patio* 30mi to Chicago
21–28 Aug
Condo rentals with a pool
Condo in Chicago
4.75 out of 5 average rating, 145 reviewsCentral Downtown Location-Modern 2BR Condo
14–21 Jul
Condo in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
8–15 Sep
Condo in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
26 Oct – 2 Nov
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
13–20 Mar
Condo in Chicago
4.7 out of 5 average rating, 27 reviews1 bedroom in the heart of downtown Chicago.
21–28 Jul
Condo in Evanston
4.94 out of 5 average rating, 71 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
24–31 Jul
Condo in Evanston
4.97 out of 5 average rating, 73 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
29 Jan – 5 Feb
Condo in Downers Grove
4.91 out of 5 average rating, 53 reviewsUpscale, Washer Dryer, Smoke Free, Pet Free,
9–16 Jun
Destinations to explore
- Downtown Chicago Holiday rentals
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