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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Home in Itasca

New place to stay

OceanFront Resort Studio at Garza Blanca Cancun MX

Welcome to Garza Blanca Resort, where Mexican hospitality meets classic Caribbean relaxation. We invite you to stay for a visit but your senses will beg you to stay forever Enjoy one of the region’s most exclusive and contemporary resorts for luxury lifestyle vacations. This is a resort that transports you entirely, and you’ll never feel like leaving Indulge in a range of world-class luxury amenities and services that ensure the ultimate getaway in paradise for you and your nearest and dearest

Home in Carol Stream

4.57 out of 5 average rating, 23 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.

Rental unit in Villa Park

4.83 out of 5 average rating, 18 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.

Guest favorite

Home in Glen Ellyn

4.94 out of 5 average rating, 18 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

Home in Bloomingdale

4.94 out of 5 average rating, 35 reviews

Whole House with a Hot Tub!

Welcome to our spacious 4-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. Book now for a spa session at our HotTub! Pool closing starting October 21st!

Rental unit in Lombard

4.83 out of 5 average rating, 46 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.

Guest favorite

Rental unit in Lombard

4.95 out of 5 average rating, 20 reviews

Smoke and Pet Free, Washer Dryer, Balcony, Cozy

Condo in Lombard

4.95 out of 5 average rating, 42 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 favorite

Home in West Chicago

5 out of 5 average rating, 11 reviews

Cozy & Specious Private Basement Apartment

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. You’ve your own private entrance & space. No SHARING!! Why Share if you can have your own private space for a reasonable rate. It is our priority to create an experience for you that is cozy, comfortable, and relaxing! Hope to see you soon!

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

Rental unit in Carol Stream

New place to stay

The oasis in Wheaton !

Forget your worries in this spacious, serene retreat. It’s cozy and my go-to spot for comfort and calm, whether I need a place to fully unwind or just a quick recharge before heading out again. This place is all about making life easier, with plenty of parking and a convenient location that keeps everything within reach—stores, highways, anything I need is close by. Day or night, I know I can rest here and feel ready to take on whatever’s next.