
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 Glen Ellyn
4.78 out of 5 average rating, 18 reviewsPardizes Suites
Guest favourite

Home in Glen Ellyn
4.95 out of 5 average rating, 20 reviewsGlen Ellyn Home
Top guest favourite

Home in Des Plaines
5 out of 5 average rating, 6 reviewsRosemont 4BD2BA house with Pool
Superhost

Home in Schaumburg
4.8 out of 5 average rating, 20 reviewsSpacious 3 Floor Townhome

Home in Plainfield
4.76 out of 5 average rating, 46 reviews30 mins to CHI• 3 Kings• BBQ Grill• Spacious• Pool
Top guest favourite

Home in Bloomingdale
4.93 out of 5 average rating, 55 reviewsNow Open: Heated Pool with Entire House

Home in Lemont
4.5 out of 5 average rating, 6 reviewsHacienda

Home in Schaumburg
Paradise with Pool & Games
Condo rentals with a pool
Guest favourite

Condo in Evanston
4.96 out of 5 average rating, 98 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

Condo in Chicago
4.28 out of 5 average rating, 18 reviewsvoco: Balcony & City View
Superhost

Condo in Lombard
4.81 out of 5 average rating, 59 reviewsSmoke & Pet Free, Washer Dryer, Fireplace, Balcony
Guest favourite

Condo in Elk Grove Village
4.93 out of 5 average rating, 86 reviewsJust remodeled apartment close to airport and mall
Guest favourite

Condo in Evanston
4.91 out of 5 average rating, 128 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Superhost

Condo in Lombard
4.91 out of 5 average rating, 47 reviewsPond View, Washer Dryer, Non Smoking Community
Guest favourite

Condo in Evanston
4.96 out of 5 average rating, 104 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

Condo in Burbank
Iconic Style, Charming Lake View
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- Guaranteed Rate Field
- 875 North Michigan Avenue
- Lincoln Park
- The Field Museum
- Washington Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Garfield Park Conservatory
- Wicker Park
- Lincoln Park Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- Chicago Cultural Center
- Things to do North Side
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- Food and drink North Side
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