
Vacation rentals with a pool in South Side
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in South Side
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 South Side rentals with a pool
House rentals with a pool

Pardizes Suites

Munster hide away

Rosemont 4BD2BA house with Pool

Family-Friendly Suburban Getaway Near Chicago

Luxury Loft with Private Pool and Movie Theater

Pool King Queen Bunk Bed Fun Munster MiniGolfHouse

Paradise with Pool & Games

Luxury fenced in modern ranch
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

Gold Coast Luxury: 2BR with Sweeping City Vistas

"Serenity of Evanston" 2 BDR/2Bath Modern Suite

Stylish Corner 2 Bedroom in the Heart of Chicago |

West Loop PH: Unmatched Views & Private Deck

Front Row to the Lake & Skyline: Epic 60th Flr 3BR

Spectacular 2BR Penthouse in the Loop | Roof Deck

Prime Lincoln Park Views + Modern Amenities Await

Beautiful Corner 2 Bedroom in the Loop | Roof Deck
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- Rentals with breakfast South Side
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- Rentals with lake access South Side
- Rentals with a fire pit South Side
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- Bed and breakfasts South Side
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- Rentals with a hot tub South Side
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- Smoking-friendly rentals South Side
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- Condo rentals South Side
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- Rentals with beach access South Side
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- Rentals with a washer and dryer South Side
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- Rentals with pools Chicago
- Rentals with pools Cook County
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- Rentals with pools United States
- Lincoln Park
- Wrigley Field
- Millennium Park
- 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
- Museum of Science and Industry
- Brookfield Zoo
- Illinois Beach State Park
- Washington Park Zoo
- Willis Tower
- The Beverly Country Club
- Raging Waves Waterpark
- The 606