
Vacation 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.
Vacation 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

Comfy 3BR 2BA, Liv+Fam Rm, Prime, 3-Car Parking

Chic Fulton Market Oasis + Curated Comfort & Style

Munster hide away

Spacious 3 Floor Townhome

Family-Friendly Suburban Getaway Near Chicago

Friends-Inspired Vintage Vibes House near Chicago

Beautiful Spanish style Home (w/inground pool)

In Ground Pool, Full Ranch Home
Condo rentals with a pool

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

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

Upscale, Smoke and Pet Free, Washer Dryer, Balcony
Other vacation rentals with a pool

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

Pardizes Suites

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

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

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

Your favorite vacation spot

Modern unit in Bridgeport-Chicago

Farm Themed Guesthouse!
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- Lincoln Park
- Wrigley Field
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- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- 875 North Michigan Avenue
- Humboldt Park
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Lincoln Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Willis Tower
- The Beverly Country Club
- Raging Waves Waterpark
- The 606
- Wilmot Mountain Ski Resort