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.

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Guest favorite

Home in Bloomingdale

4.96 out of 5 average rating, 23 reviews

Giant Swimming Pool with Whole House!

Welcome to our spacious 5-bedroom home! Enjoy lounging in the airy living area or cooking in the fully equipped kitchen. With a master bedroom featuring a king bed and en-suite, a second bedroom with a king bed, a third with a queen, and an office space for the fourth bedroom, so there's plenty of room. Plus, unwind with a game of pool on the basement's pool table. High-speed internet keeps you connected. Welcome to your home away from home! Book now for a swim! **HotTub coming September 2nd!!**

Home in Carol Stream

4.8 out of 5 average rating, 5 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 TVs through your personal apps.

Townhouse in Warrenville

5 out of 5 average rating, 3 reviews

Pet-Friendly Warrenville Townhome w/ Gas Grill!

Experience a delightful getaway in this stylish 2-bedroom, 2.5-bath vacation rental in Warrenville, Illinois! This townhome offers desirable amenities like a community pool for refreshing dips, a balcony for evening grill sessions, and a dedicated workspace for when you need to get some work done. Enjoy the Naperville Riverwalk for serene nature views, take the family to Sugar Grove Family Fun Center, or venture out to nearby Chicago for an urban adventure. Then, relax in the cozy living room!

Rental unit in Villa Park

4.77 out of 5 average rating, 13 reviews

Walkable area in Chicago suburb

The unit is in a family-friendly complex with an outdoor pool and gym. The complex directly connects to 2 walking/biking trails, the Illinois Prairie Path, and Great Western Trail. There are playgrounds along the trail and leads to the main street of neighboring towns. Your family will be close to everything when you stay at this centrally-located place. Walk score of 81, restaurants, bars, grocery stores, fast food, and Walmart are all <1 mile away. Close to Elmhurst Hospital and ORD.

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

Home in Glen Ellyn

4.74 out of 5 average rating, 19 reviews

Glen Ellyn Home

Come stay at this beautiful home located in a quiet neighborhood with everything you need for a relaxing getaway. Home has access to nearby restaurants and fast food just minutes away. Mins away from Downtown Glen Ellyn and 40 minutes from Downtown Chicago. Close to Schaumburg, Oakbrook and Yorktown Mall. 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

Guest favorite

Rental unit in Lombard

4.8 out of 5 average rating, 25 reviews

Balcony, Pond View, Washer Dryer, Smoke 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 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

Rental unit in Lombard

4.82 out of 5 average rating, 44 reviews

Balcony, Pond View, Washer Dryer, Non Smoking

Superhost

Condo in Lombard

4.95 out of 5 average rating, 39 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.

Rental unit in Naperville

4.61 out of 5 average rating, 23 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

Guest favorite

Home in Bensenville

5 out of 5 average rating, 9 reviews

New! Arcade+Sauna+Slots+Karaoke by O’Hare

Welcome to Bensenville Hidden Haven: Your Ideal Chicago Getaway! Conveniently near O'Hare Airport and minutes from River Forest and White Pines Golf Clubs, our retreat offers relaxation and fun. Enjoy the indoor heated pool, sauna, steam shower, arcade room, massage chairs, slot machines, and karaoke. Located in a peaceful neighborhood with a large park nearby, it's perfect for the whole family. We look forward to welcoming you!

Guest favorite

Home in West Chicago

5 out of 5 average rating, 6 reviews

Cozy & Specious 1 bedroom lower level Apt

It’s a completely separate space with its own entrance & electronic keypad. Nice and clean place to stay in West Chicago and call it your home during your personal or business trip. You'll enjoy the accessibility to all nearby restaurants, grocery stores and shopping mall. Close to major highways. It is our priority to create an experience for you that is cozy, comfortable, and relaxing! Hope to see you soon!