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

Home in Carol Stream

4.86 out of 5 average rating, 7 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

Superhost

Home in Carol Stream

4.42 out of 5 average rating, 24 reviews

Amazing Summer Pool Awaits You!

Vacation, Staycation or Business, you will love your stay at this beautiful paradise with heated pool and tri-level entertainment deck equipped with grill and outside seating and gazebo! Semi-secluded backyard, walking distance to bike path, playground, skate park, walking trails, restaurants and even the gym! Relax on the magnificent deck while watching the sunset This home is pet free and smoke free. Pool is available May-Sept. WiFi is available throughout and Smart TV in the family room.

Guest favourite

Home in Glen Ellyn

4.95 out of 5 average rating, 20 reviews

Glen Ellyn Home

Come stay at this beautiful home located in a quiet neighborhood with everything you need for a relaxing getaway. Nearby restraunts. Mins away from Downtown Glen Ellyn and 40 minutes from Downtown Chicago. Close to a major highway and focal point to travel anywhere. Beautiful home with everything you need from pool, firepit, indoor and outdoor kitchen, arcade system for kids and foosball. PARTY EVENT PACKAGE FOR 20 GUEST MAX, $1,000-2,000 WITH FEES FOR SELECT EVENTS ONLY MINIMUM 3 DAY STAY

Superhost

Flat in Warrenville

New place to stay

1BR Naperville | 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. 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 w/ firepits, a fitness center, pool table, pickleball court, and in-unit laundry - convenience is at your fingertips!

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.

Apartment in Lombard

4.84 out of 5 average rating, 56 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.

Flat in Lombard

4.75 out of 5 average rating, 16 reviews

Smoke and Pet Free, Washer Dryer, Wood Fireplace

Flat in Lombard

4.74 out of 5 average rating, 34 reviews

Balcony, Pond View, Washer Dryer, Smoke Free

Apartment in Lombard

4.93 out of 5 average rating, 46 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

Apartment in Downers Grove

4.92 out of 5 average rating, 63 reviews

Upscale, Washer Dryer, Smoke Free, Pet Free,

If you’re looking for the ideal place to feel at home that's affordable, close to Downtown Chicago, Wheaton, Oakbrook, shopping, dining, highways, there’s nothing better than this fully furnished unit. It's recently renovated, offers the modern conveniences you could want. It includes everything you need from free parking, linens to dishes, cookware, cable, wireless internet, king size bed, in-unit washer - dryer, 2 smart TV’s, Alexa, LED fireplace, basic cable, and Netflix.

Guest favourite

Home in West Chicago

4.86 out of 5 average rating, 22 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 for rent.. Max 15 people allowed! Inground heated pool with deep & shallow end. Pool size 16x22.

Guest favourite

Home in West Chicago

4.88 out of 5 average rating, 8 reviews

Cloud 9: 4BR, Pool, Fully Fenced

This inviting two-story home is designed for comfort, entertainment, and relaxation. The pool is officially open for the season! Kids love this place—there’s a sandbox, water table, and swings to keep them busy for hours. Enjoy the open-concept layout, a loft for work or reading, and a fun lower-level game room with a pool table. Outside, soak up the sun with outdoor dining, lounge chairs, and plenty of space to unwind. This 4 bedroom home is perfect for your stay!