Holiday 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 favourite

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

4.83 out of 5 average rating, 12 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 inthrough your personal apps

Home in Elmhurst

4.5 out of 5 average rating, 14 reviews

Lucky #7 w/ Gym

Welcome to Lucky Number 7! Relax, unwind, and spread out in this beautifully renovated single -level ranch—perfectly designed for comfort, connection, and fun. This spacious home features an open-concept living room, dining area, and kitchen. All brand new and thoughtfully styled to make you feel right at home. The finished basement is equipped with a game room, bar and in-home gym. Have a great time in the sparkling above-ground pool. Let’s make some unforgettable memories in Lucky Number 7!

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 favourite

Home in Bartlett

5 out of 5 average rating, 11 reviews

Elegant Executive Residence, Hot Tub/Pool/Parties!

Escape to your own private retreat, modern charm meets cozy comfort in this beautifully designed space. Unwind with luxe bedding, a full kitchen, fast Wi-Fi, and a serene outdoor deck perfect for morning coffee or stargazing. Quick drive to local shops in Geneva or Elgins downtown, dining, and trails. Ideal for families, couples, or remote work getaways. Your peaceful, picture-perfect stay awaits! Leave your worries at the door, house for all to enjoy! 35 min to O’Hare and 45 to Chicago

Top Guest favourite

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, 18 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 w/ 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!

Guest favourite

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, 67 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.

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

4.79 out of 5 average rating, 24 reviews

Smoke and Pet Free, Washer Dryer, Wood Fireplace

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

4.92 out of 5 average rating, 51 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.

Guest favourite

A modern two-story home is set on a spacious lot with a well-maintained driveway. The exterior features blue siding and large windows, allowing natural light to fill the interior. A covered entrance leads to the front door, surrounded by green grass and shrubs.

Home in West Chicago

4.88 out of 5 average rating, 25 reviews

Cozy & Relax Escape

You are booking a Cozy, Modern, and SPACIOUS Basement Apartment with a Private Entrance, and a large open-concept Guest Suite! Located in one of West Chicago incorporated quiet neighborhoods. Host occupies the separate 1st floor. You’ve your own private entrance & space. No SHARING!! Why Share if you can have your own private space for a reasonable rate. Pool is available during pool season. Inground heated pool with deep & shallow end. Pool size 16x22.

A spacious living area presents a black sofa adorned with yellow cushions, accompanied by a large abstract rug. The open layout connects to a modern kitchen featuring light cabinetry and stainless-steel appliances, with a dining area visible in the background.

Apartment in Naperville

4.62 out of 5 average rating, 26 reviews

Lovely 2-Bdrm unit with pool. Home away from home.

Come relax, enjoy, and make yourself at home in this stylish 2 bedroom/2 bath in the heart of Naperville. Located near the Naperville Riverwalk, Fox Valley Mall, Top Golf, and a ton of restaurants. Just to name a few a fun things you can do. The space Entire unit Free Parking TV in each room Washer/ Dryer in unit Free Wi-Fi Balcony Central air Microwave Toaster Keurig Per Covid Regulations: Unit is cleaned and sanitized after each guest

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

4.9 out of 5 average rating, 50 reviews

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

Guest favourite

Home in Elmhurst

5 out of 5 average rating, 14 reviews

Elmhurst 4BR Home with Pool | Mid-Term Ready

✨ Beautiful & Spacious Home with Pool ✨ Perfect for families and groups, this home offers 3 bedrooms and 1 bath on the main floor, plus a luxurious master suite upstairs with a walk-in shower, huge closet, and laundry room. Enjoy the open-concept living room, fully equipped kitchen, and a stunning backyard with a pool the ideal spot for relaxation and fun during your stay!