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.

1 of 1 pages1 / 1

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

4.89 out of 5 average rating, 18 reviews

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

LocationFamilyOutdoor spaces

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

5 out of 5 average rating, 33 reviews

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!

ValueLocationView

Top guest favorite

A stylish living area features a beige sofa adorned with yellow and blue cushions. A small table with four chairs is positioned near a large window that opens to a balcony. Artwork with abstract designs is displayed on the blue accent wall.

Apartment in Warrenville

5 out of 5 average rating, 30 reviews

Naperville Family Fun! Pool, Pickleball, Kids Room

A premium, resort-like experience in a professionally managed 2-bedroom / 2-bathroom property, providing the perfect balance of luxury and comfort for business travelers and families. Enjoy the pool, pickleball court, kids' play room, courtyard with firepits, fitness center, pool table, and sauna - convenience is at your fingertips! Explore nearby downtown Naperville (8 mins), classy Oakbrook Terrace, the beautiful Morton Arboretum, and downtown Chicago, a short drive or train ride away!

FamilyLocationLaundry

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.

Guest favorite

Apartment in Warrenville

4.96 out of 5 average rating, 25 reviews

River Views 2BR Haven | Pool, Gym, Pickleball

ValueLocationComfort

Guest favorite

Apartment in Warrenville

4.83 out of 5 average rating, 6 reviews

Resort-Style 2BR Gateway | Sauna, Pool, BBQ, Gym

A premium, resort-like experience in a professionally managed 2-bedroom / 2-bathroom property, providing the perfect balance of luxury and comfort for business travelers and families. Enjoy the pool, pickleball court, kids' playroom, courtyard with firepits, fitness center, pool table, and sauna - convenience is at your fingertips! Explore nearby downtown Naperville (8 mins), classy Oakbrook Terrace, the beautiful Morton Arboretum, and downtown Chicago, a short drive or train ride away!

FamilyIndoor spacesComfort

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

4.82 out of 5 average rating, 71 reviews

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

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.

LocationFamilyTV

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

4.74 out of 5 average rating, 27 reviews

Smoke and Pet Free, Washer Dryer, Wood Fireplace

LocationFamilyLayout

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

4.83 out of 5 average rating, 58 reviews

Balcony, Pond View, Washer Dryer, Non Smoking

ValueLocationCheckout

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

4.78 out of 5 average rating, 46 reviews

Balcony, Pond View, Washer Dryer, Smoke Free

LocationFamilyLong stay

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

4.87 out of 5 average rating, 55 reviews

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.

LocationValueAmenities

Superhost

A cozy living area features a dark sectional sofa facing a wall-mounted smart TV. A round coffee table sits in front, accompanied by greenery and decorative items. Natural light streams in through large windows adorned with sheer curtains, creating a warm and inviting ambiance.

Apartment in Lombard

4.9 out of 5 average rating, 29 reviews

Quiet Balcony Retreat • Parking • In-Unit Laundry

Quiet, comfortable 1BR apartment in Lombard. Perfect for business travel, medical visits, or extended stays. Includes private balcony, fast Wi-Fi, Smart TV, free parking, and in-unit washer & dryer. Queen bedroom with blackout curtains and spacious closet. Fully stocked kitchen and cozy living area for relaxing or working. Conveniently located near Yorktown Mall, Oakbrook, dining, grocery stores, coffee shops, and major highways. Smooth, reliable stay exactly as pictured.

ValueLocationNearby