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.
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Vacation rentals for every style
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Popular amenities for North Side rentals with a pool
House rentals with a pool
Guest favourite
Home in Glen Ellyn
4.94 out of 5 average rating, 18 reviewsGlen Ellyn Home
Guest favourite
Home in Chicago
4.86 out of 5 average rating, 29 reviews2Bed+2Bath PentHouse in South Loop
Guest favourite
Home in Bloomingdale
4.94 out of 5 average rating, 35 reviewsWhole House with a Hot Tub!
Superhost
Home in Schaumburg
4.82 out of 5 average rating, 11 reviewsSchaumburg Oasis with a Pool and Hidden Garden
Home in Chicago
New place to stayCity Close, Country Calm
Guest favourite
Home in Schaumburg
4.95 out of 5 average rating, 20 reviewsParadise 4BR w/ Pool & Games
Guest favourite
Home in Schaumburg
4.96 out of 5 average rating, 25 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Condo rentals with a pool
Condo in Downers Grove
4.92 out of 5 average rating, 59 reviewsUpscale, Washer Dryer, Smoke Free, Pet Free,
Guest favourite
Condo in Evanston
4.95 out of 5 average rating, 84 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Condo in Chicago
4.69 out of 5 average rating, 39 reviews2BD Central Downtown Location! Spacious & Cozy
Guest favourite
Condo in Evanston
4.96 out of 5 average rating, 94 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Guest favourite
Condo in Evanston
4.91 out of 5 average rating, 117 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Condo in Chicago
4.8 out of 5 average rating, 25 reviewsLovely condo studio
Guest favourite
Condo in Evanston
4.96 out of 5 average rating, 90 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
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