Vacation rentals with a pool in DuPage County

4.89 out of 5 average rating, 19 reviews

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

ValueFamilyGetting around

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

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!

ValueLocationIndoor spaces

5.0 out of 5 average rating, 32 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.

5.0 out of 5 average rating, 6 reviews

Apartment in Elmhurst

Chicago Burbs Gem | Garage, King Beds, Gym, Pool!

Indulge in elevated comfort at this luxury, professionally-managed 2BR/2BA apartment in lively downtown Elmhurst. Steps from cafés, boutiques, and the Metra for quick trips to Chicago, with Oakbrook and O’Hare minutes away. Relax with a resort-style pool, a full fitness center, secure garage parking, fire pits in the courtyard, a pool table, and a movie theater. Spacious king bedrooms, a modern kitchen, in-unit laundry, fast Wi-Fi, and smart TVs make every stay effortless and memorable.

LocationValueBathroom

5.0 out of 5 average rating, 9 reviews

Home in Oak Brook

Gym, Steam Room, Sauna Jacuzzi & Pickleball Court

Oak Brook Secluded Architectural masterpiece on corner of York and Canterberry Heated circular driveway. Foyer elevator to easily maneuver between all 4 levels. Outdoor pool, spa, sports court, and putting green as well as a guest house with full kitchen and bedroom/bath. 1st fl gym, spa, office w/ fireplace & patio. 2nd floor: library, master w/sitting room, fireplace and spa-like bath. Lower level: bar, rec room, wine cellar, game room, golf simulator, and 2 bedroom suites w/bath.

FamilyLocationCleanliness

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.

4.83 out of 5 average rating, 60 reviews

Balcony, Pond View, Washer Dryer, Non Smoking

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.

ValueLocationQuiet

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.

4.71 out of 5 average rating, 28 reviews

Smoke and Pet Free, Washer Dryer, Wood Fireplace

ValueLocationHospitality

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.

4.78 out of 5 average rating, 46 reviews

Balcony, Pond View, Washer Dryer, Smoke Free

FamilyValueCheckout

4.76 out of 5 average rating, 72 reviews

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

ValueFamilyAccuracy

4.88 out of 5 average rating, 58 reviews

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.

ValueLocationCleanliness

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.

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.

LocationValueKitchen