Vacation rentals with a pool in DuPage County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in DuPage County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

The exterior of a spacious two-story home is shown, featuring a mixture of brick and siding. Lush green landscaping surrounds the house, with trees casting shade across the front yard. A paved driveway leads to a garage, and a clear blue sky provides a bright backdrop.

Home in Carol Stream

Spacious 4 Bed/3.5 Bath Sleeps 8+

Just 30 minutes from downtown Chicago! You will love this gorgeous 4-bedroom home perfect for a vacation, staycation or business travel! Walking distance to the playground & walking trails, restaurants and even the local gym! Home has free parking, 3.5 baths, fully finished basement equipped with work-out room! May-Sept you can enjoy the deck, gazebo, outdoor gas grill & heated 27’ pool! Home is pet free and smoke free. Wi-Fi to enjoy your programs on the Smart TV ithrough your personal apps

4.89 out of 5 average rating, 19 reviews

Top guest favorite

The living area features a modern couch adorned with yellow and white pillows, accompanied by two accent chairs. A dining table with blue chairs is set on a cozy area rug. Natural light enters through sliding glass doors, leading to a small balcony.

Apartment in Warrenville

Spacious 2BR Hideaway | Pool, Gym & Pickleball!

A premium, resort-like experience in a professionally managed property, providing the perfect balance of luxury and comfort for business travelers and families. Explore nearby downtown Naperville (8 mins), classy Oakbrook Terrace, the beautiful Morton Arboretum, and downtown Chicago, a short drive or train ride away! Enjoy countless amenities, including the pool, courtyard with firepits, a fitness center, pool table, pickleball court, and in-unit laundry - convenience is at your fingertips!

5.0 out of 5 average rating, 33 reviews

A group of deer is observed grazing in a grassy area, surrounded by trees. The warm light of dusk casts a gentle glow over the scene, highlighting the soft contours of the landscape and the deer's slender forms.

Home in Bolingbrook

Peaceful backyard oasis. Unique!

Minutes from Naperville, 30 minutes to Chicago yet you feel like you are in the country in the backyard. The home backs up to wooded lands. Sipping coffee in the backyard you’ll have many choices of where to hang out. You’ll see Blue Jays, Cardinals, yellow finches, woodpeckers, hummingbirds among many other water birds and high flyers. You may even see a coyote or two roaming. In the evening you’ll see many deer and beautiful skies at sunset. Pool, pool table and fire pit. Large rooms.

Superhost

A modern living room is furnished with a spacious sectional sofa, light-colored coffee table, and accent chairs. A dining area is visible in the background, seating six at a large table. The kitchen features a bar with stools, enhancing the open layout.

Apartment in Lombard

Smoke and Pet Free, Washer Dryer, Wood Fireplace

Welcome to our cozy retreat! Fully furnished for affordability and convenience, our prime location near Downers Grove, Wheaton, Oakbrook, and Downtown Chicago ensures the perfect base for your stay. Enjoy free parking, washer-dryer, dishwasher, and amenities like linens, dishes, cookware, cable, wireless internet, queen-size beds, smart TV, and Hulu access. Little touches make guests feel truly at home, creating a delightful and memorable stay, whether for business or leisure.

4.71 out of 5 average rating, 28 reviews

Superhost

A cozy living area is highlighted by a wood-burning fireplace, where a warm fire flickers. A sleek coffee table sits in front of a comfortable sectional sofa, complemented by a textured area rug. Two glasses of wine rest atop the table, adding a touch of relaxation.

Condo in Lombard

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

4.82 out of 5 average rating, 71 reviews

Superhost

A cozy living room space features a comfortable sofa adorned with decorative pillows. A sleek coffee table sits atop a soft carpet, complemented by a green potted plant. Large sliding glass doors provide access to a private balcony, enhancing natural light in the area.

Apartment in Lombard

Balcony, Pond View, Washer Dryer, Non Smoking

4.83 out of 5 average rating, 58 reviews

Superhost

A cozy living area features a comfortable gray sectional sofa and a round coffee table with plants and decorative items. Behind, a dining space with a table for four is visible, along with framed artwork on the walls and a large round mirror. Light floods the space.

Apartment in Lombard

Balcony, Pond View, Washer Dryer, Smoke Free

4.78 out of 5 average rating, 46 reviews

Superhost

A comfortable living area features a dark sofa, coffee table, and a modern TV stand with a large television. A dedicated dining space with a round table for two is visible. Sliding glass doors lead to a private balcony, providing natural light and outdoor views.

Condo in Lombard

Pond View, Washer Dryer, Non Smoking, Pet Free

Welcome to our cozy retreat! Fully furnished for affordability and convenience, our prime location near Downers Grove, Wheaton, Oakbrook, and Downtown Chicago ensures the perfect base for your stay. Enjoy free parking, washer-dryer, dishwasher, and amenities like linens, dishes, cookware, cable, wireless internet, queen-size bed, smart TV, and Hulu access. Little touches make guests feel truly at home, creating a delightful and memorable stay, whether for business or leisure.

4.88 out of 5 average rating, 58 reviews

Top guest favorite

Villa in Wood Dale

Fun 5BR 4.5BA, Pool, Hot Tub, Game Rm, Near O’Hare

Welcome to this spacious and comfortable home in Wood Dale, ideally located near O’Hare Airport and Downtown Chicago. Perfect for families and groups, this home features multiple bedrooms, a fully equipped kitchen, free parking, and relaxing living spaces. Enjoy easy access to shopping, restaurants, parks, and nearby attractions. Whether you're visiting for business or leisure, this home offers comfort, convenience, and great value for your stay.

5.0 out of 5 average rating, 64 reviews

Superhost

A cozy living area features a sectional sofa adorned with pillows and a throw pillow inscribed with 'Enjoy.' A round coffee table holds decorative items, while framed art showcases serene designs on the wall. A small dining area is visible in the background.

Condo in Lombard

Pond View, Washer Dryer, Non Smoking Community

Our cozy condo is the ideal place to feel at home. Affordable, close to Downtown Chicago, Downers Grove, Wheaton, Oakbrook, shopping, dining, highways. there is nothing better than this fully furnished unit. Includes everything you need from free parking, linens to dishes, cookware, cable, wireless internet, queen size bed, sofa sleeper, LED fireplace, in-unit washer - dryer, smart TV’s, Hulu and Hulu Live

4.88 out of 5 average rating, 52 reviews

Guest favorite

Home in Elmhurst

The Gathering House & Cinema

This spacious 6-bedroom home is built for making memories: dive into the private pool, unwind in the jacuzzi, then gather everyone for movie night in our home theater. Perfect for family reunions, friend getaways, celebrations, or any group that wants a home base to relax and reconnect. Pool, jacuzzi, home theater, 6 bedrooms — everything you need under one roof. Come make it your home away from home.

4.83 out of 5 average rating, 6 reviews

Guest favorite

A spacious living area is characterized by a plush gray sofa and a round coffee table. Decorative wall elements and a vibrant red holiday tree enhance the modern decor. Soft lighting is provided by a statement chandelier hanging from the ceiling.

Home in Glendale Heights

Pardizes Suites

Pardizes Suites is truly a wonderful sanctuary! It's not just a place to live; it's a space that reflects comfort and warmth. Every corner of your home tells a story, from the inviting living room that beckons for cozy gatherings to the beautiful outdoor area that offers the perfect retreat for relaxation.

4.85 out of 5 average rating, 27 reviews