
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
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 Evanston
4.89 out of 5 average rating, 44 reviewsBeautiful Historic Colonial

Home in Glen Ellyn
4.67 out of 5 average rating, 3 reviewsPardizes Suites

Home in Glen Ellyn
4.95 out of 5 average rating, 20 reviewsGlen Ellyn Home
Superhost

Home in Schaumburg
4.9 out of 5 average rating, 21 reviewsSchaumburg Oasis with a Pool and Hidden Garden
Superhost

Home in Lake Forest
4.9 out of 5 average rating, 63 reviewsBeautiful 137 Year Old Farm Home (3night min)
Condo rentals with a pool
Guest favorite

Condo in Downers Grove
4.92 out of 5 average rating, 61 reviewsUpscale, Washer Dryer, Smoke Free, Pet Free,
Guest favorite

Condo in Evanston
4.96 out of 5 average rating, 91 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Guest favorite

Condo in Evanston
4.96 out of 5 average rating, 102 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Condo in Chicago
4.2 out of 5 average rating, 5 reviewsvoco: Balcony & City View
Guest favorite

Condo in Elk Grove Village
4.94 out of 5 average rating, 83 reviewsJust remodeled apartment close to airport and mall
Guest favorite

Condo in Evanston
4.91 out of 5 average rating, 124 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba

Condo in Chicago
4.8 out of 5 average rating, 25 reviewsLovely condo studio
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- Millennium Park
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