
Vacation rentals with a pool in Cook County
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Top-rated rentals with a pool in Cook County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Cook County rentals with a pool
House rentals with a pool

Cozy house in Schererville

Pool & Beach Haven-private pool, steps to beach!

Spacious 3 Floor Townhome

30 mins to CHI• 3 Kings• BBQ Grill• Spacious• Pool

Now Open: Heated Pool with Entire House

Entire House With Pool - Backyard Beach Getaway

Schaumburg Oasis:Private Pool & Enchanted Garden

Cloud 9: 4BR, Pool, Fully Fenced
Condo rentals with a pool

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

voco: Balcony & City View

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

Just remodeled apartment close to airport and mall

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

Pond View, Washer Dryer, Non Smoking Community

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

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
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