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

Chic Fulton Market Oasis + Curated Comfort & Style

Luxury fenced in modern ranch

Elmhurst Luxury 4BR w/ Pool, Fenced Yard, Downtown

Rosemont 4BD2BA house with Pool

Lucky #7 w/ Gym

Luxury Loft with Private Pool and Movie Theater
Condo rentals with a pool

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

Harmony of Evanston 1 BDR Exec Suite w/pool & Gym

Best view and luxury style, Located in Downtown

Just remodeled apartment close to airport and mall

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

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

Iconic Style, Charming Lake View
Other vacation rentals with a pool

Enjoy our Des Plaines/Chicago 2-Bed Guest House!

Modern Mount Prospect 2 Bedroom

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

Stylish Corner 2 Bedroom in the Heart of Chicago |

50th Floor Mag Mile VIEWS, Balcony, Pool, Gym

The Millennium Manor

Stunning 3BR Penthouse in the Loop | Roof Deck

Spacious luxury studio apartment
Quick stats about vacation rentals with a pool in Near North Side
Total rentals
770 properties
Nightly prices starting at
R698 ZAR before taxes and fees
Total number of reviews
7.3K reviews
Family-friendly rentals
220 properties are a good fit for families
Pet-friendly rentals
520 properties allow pets
Rentals with dedicated workspaces
390 properties have a dedicated workspace
Destinations to explore
- Pet-friendly rentals Near North Side
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- Rentals with an EV charger Near North Side
- Rentals with a fire pit Near North Side
- Family-friendly rentals Near North Side
- Rentals with an accessible height bed Near North Side
- Rentals with beach access Near North Side
- Rentals with a sauna Near North Side
- House rentals Near North Side
- Condo rentals Near North Side
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- Fitness-friendly rentals Near North Side
- Rentals with a hot tub Near North Side
- Townhouse rentals Near North Side
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- Waterfront rentals Near North Side
- Rentals with a patio Near North Side
- Rentals with outdoor seating Near North Side
- Rentals with pools Chicago
- Rentals with pools Cook County
- Rentals with pools Illinois
- Rentals with pools United States
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- Humboldt Park
- 875 North Michigan Avenue
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
- Brookfield Zoo
- Museum of Science and Industry
- Washington Park Zoo
- Willis Tower
- The Beverly Country Club
- Raging Waves Waterpark
- The 606