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

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.

Top guest favourite

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.

Flat in Warrenville

5 out of 5 average rating, 14 reviews

Luxury 2BR - Pool, Pickleball, Gym, Sauna & More!

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, courtyard w/ firepits, a fitness center, pool table, sauna, and in-unit laundry - 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!

Home in Bartlett

5 out of 5 average rating, 4 reviews

Elegant Executive Residence, Hot Tub & Pool

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

Guest favourite

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.

Flat in Lombard

4.96 out of 5 average rating, 27 reviews

Balcony • In-Unit Laundry • Free Parking

Smoke free 1BR apartment in a quiet Lombard location. Perfect for business travel, medical visits, or long-term stays. Enjoy your own private balcony, in-unit washer/dryer, fast WiFi, Smart TV, and free parking. The bedroom features a comfortable queen bed, blackout curtains, and large closet. The kitchen is fully stocked for cooking, and the living room offers a cozy space to relax or work. Close to Yorktown Mall, Oakbrook, grocery stores, dining, coffee shops, and major highways.

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.

Apartment 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.

Flat in Lombard

4.83 out of 5 average rating, 23 reviews

Smoke and Pet Free, Washer Dryer, Wood Fireplace

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.

Flat in Lombard

4.82 out of 5 average rating, 50 reviews

Balcony, Pond View, Washer Dryer, Non Smoking

Superhost

A modern living area features a comfortable sectional sofa with decorative cushions, a central coffee table, and an area rug with a striped pattern. A large wall-mounted television and framed artwork adorn a dark accent wall, while the kitchen with stainless steel appliances is visible in the background.

Flat in Warrenville

5 out of 5 average rating, 3 reviews

1BR Naperville Gem | Pickleball, Pool, Gym & More!

A premium, resort-like experience in a professionally managed property, providing the perfect balance of luxury and comfort for business travelers and families. Enjoy the pool, pickleball court, courtyard w/ firepits, a fitness center, pool table, sauna, and in-unit laundry - 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 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, 24 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.

Flat 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

Flat in Naperville

4.83 out of 5 average rating, 6 reviews

7 Min From Downtown Naperville!

✨ Modern 1BR Business Retreat – 7 min to Downtown Naperville ✨ Fully furnished & freshly updated first floor unit, ideal for traveling nurses or long business stays. 🛋 In-unit washer/dryer, 💻 fast Wi-Fi and Ethernet line into router. Enjoy 🏋️ full gym, 🏊 two pools, 🔥 fire pits & a 🌊 pond view with fountain from your private patio. 🚗 Easy access to highways & Metra. Two night minimum, new management & stylish comfort throughout!