
Holiday rentals with a pool in Oak Brook
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Oak Brook
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Oak Brook rentals with a pool
House rentals with a pool

Cozy house in Schererville

Munster hide away

Spacious 3 Floor Townhome

30 mins to CHI_3 Kings_BBQ Grill_Spacious_Pool

Luxury Loft with Private Pool and Movie Theater

Beautiful Spanish style Home (w/inground pool)

Beautiful 137 Year Old Farm Home (3night min)

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
Other holiday rentals with a pool

5 bdrm/2.5 bth/Fenced Yard/Quiet St /Pet friendly

Glen Ellyn Home

Lovely 2-Bdrm unit with pool. Home away from home.

Play in the Windy City and rest by the “606”

Cozy Family 3BR Oasis: Park, Private Yard, & BBQ!

Modern unit in Bridgeport-Chicago

Farm Themed Guesthouse!

Spacious Family Glenwood Estates Home w/ Hot Tub!
Destinations to explore
- Chicago Holiday rentals
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- 875 North Michigan Avenue
- The Field Museum
- Illinois Beach State Park
- Wicker Park
- Brookfield Zoo
- Museum of Science and Industry
- Garfield Park Conservatory
- Lincoln Park Zoo
- Raging Waves Waterpark
- Willis Tower
- The 606
- The Beverly Country Club
- Deep River Waterpark