Vacation rentals with a pool in Chicago
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Chicago
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 Chicago rentals with a pool
House rentals with a pool
Home in New Lenox
4.75 out of 5 average rating, 55 reviewsCheerful home. Heated pool, Hot tub!
Home in Glen Ellyn
4.94 out of 5 average rating, 18 reviewsGlen Ellyn Home
Home in Olympia Fields
4.53 out of 5 average rating, 40 reviewsLuxurious South Suburban Villa
Home in Near South Side
4.86 out of 5 average rating, 29 reviews2Bed+2Bath PentHouse in South Loop
Home in Plainfield
4.81 out of 5 average rating, 36 reviews30 mins to CHI*3 Kings*Fireplace*2 Desks*BBQ Grill
Home in Schaumburg
4.82 out of 5 average rating, 11 reviewsSchaumburg Oasis with a Pool and Hidden Garden
Home in Glenwood
4.79 out of 5 average rating, 53 reviewsSpacious Family Glenwood Estates Home w/ Hot Tub!
Home in Itasca
New place to stayOceanFront Resort Studio at Garza Blanca Cancun MX
Condo rentals with a pool
Condo in Downers Grove
4.92 out of 5 average rating, 59 reviewsUpscale, Washer Dryer, Smoke Free, Pet Free,
Condo in Evanston
4.95 out of 5 average rating, 83 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Condo in Evanston
4.96 out of 5 average rating, 91 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Condo in Oak Lawn
5 out of 5 average rating, 7 reviews1flr Spacious-3Bedrooms/2 Bath w Garage Parking
Condo in Elk Grove Village
4.94 out of 5 average rating, 71 reviewsJust remodeled apartment close to airport and mall
Condo in Uptown
4.8 out of 5 average rating, 25 reviewsLovely condo studio
Condo in Evanston
4.91 out of 5 average rating, 117 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Condo in Evanston
4.96 out of 5 average rating, 89 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
Quick stats about vacation rentals with a pool in Chicago
Total rentals
1.1K properties
Total number of reviews
11K reviews
Family-friendly rentals
320 properties are a good fit for families
Pet-friendly rentals
670 properties allow pets
Rentals with dedicated workspaces
780 properties have a dedicated workspace
Wifi availability
1.1K properties include access to wifi
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Evanston Vacation rentals
- Saugatuck Vacation rentals
- Holland Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Bend Vacation rentals
- South Side Vacation rentals
- Schaumburg Vacation rentals
- Rentals with pools United States
- Lake house rentals Chicago
- Rentals with a washer and dryer Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Smoking-friendly rentals Chicago
- Beachfront rentals Chicago
- Townhouse rentals Chicago
- Condo rentals Chicago
- Rentals with a hot tub Chicago
- House rentals Chicago
- Bed and breakfasts Chicago
- Rentals with a fireplace Chicago
- Rentals with lake access Chicago
- Monthly Rentals Chicago
- Private suite rentals Chicago
- Rentals with an EV charger Chicago
- Family-friendly rentals Chicago
- Kid-friendly rentals Chicago
- Mansion rentals Chicago
- Fitness-friendly rentals Chicago
- Rentals with a home theater Chicago
- Rentals with outdoor seating Chicago
- Rentals with beach access Chicago
- Rentals with an accessible height bed Chicago
- Rentals with a patio Chicago
- Loft rentals Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Rentals with a sauna Chicago
- Rentals with a balcony Chicago
- Apartment rentals Chicago
- Waterfront rentals Chicago
- Rentals with pools Downtown Chicago
- Rentals with pools Milwaukee
- Rentals with pools Lake Geneva
- Rentals with pools Illinois
- Rentals with pools Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Things to do United States
- Sports activities United States
- Food and drink United States
- Art and culture United States
- Wellness United States
- Sightseeing United States
- Entertainment United States
- Nature and outdoors United States
- Things to do Illinois
- Art and culture Illinois
- Food and drink Illinois
- Sightseeing Illinois
- Things to do Cook County
- Food and drink Cook County
- Sightseeing Cook County
- Art and culture Cook County
- Nature and outdoors Cook County
- Things to do Chicago
- Sightseeing Chicago
- Art and culture Chicago
- Food and drink Chicago