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.
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Holiday 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
Home in Plainfield
4.81 out of 5 average rating, 36 reviews30 mins to CHI*3 Kings*Fireplace*2 Desks*BBQ Grill
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, 36 reviewsWhole House with a Hot Tub!
Superhost
Home in Schaumburg
4.85 out of 5 average rating, 13 reviewsSchaumburg Oasis with a Pool and Hidden Garden
Home in Chicago
New place to stayCity Close, Country Calm
Guest favourite
Home in Carol Stream
4.86 out of 5 average rating, 7 reviewsSpacious 4 Bed/3.5 Bath Sleeps 8+
Apartment rentals with a pool
Guest favourite
Apartment in Evanston
4.95 out of 5 average rating, 84 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Apartment in Chicago
4.69 out of 5 average rating, 39 reviews2BD Central Downtown Location! Spacious & Cozy
Guest favourite
Apartment in Evanston
4.96 out of 5 average rating, 94 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Guest favourite
Apartment in Oak Lawn
5 out of 5 average rating, 7 reviews1flr Big! 3Bedrooms/2 Bath w Garage Parking
Guest favourite
Apartment in Evanston
4.91 out of 5 average rating, 117 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Apartment in Chicago
4.8 out of 5 average rating, 25 reviewsLovely condo studio
Guest favourite
Apartment in Evanston
4.96 out of 5 average rating, 90 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
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