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 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

An outdoor space features a gazebo and comfortable seating, framed by vibrant flowers. The heated above-ground pool is visible, surrounded by a wooden deck. Lush greenery serves as a backdrop, creating a serene setting enhanced by soft evening light.

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 favorite

A swimming pool is seen surrounded by a white fence, with colorful pool floats inviting fun. Sunlight reflects off the clear blue water, and lush green trees provide a natural backdrop. A patterned mat lies at the edge, enhancing the relaxing atmosphere.

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

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

4.84 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.

Guest favorite

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.

Apartment in Lombard

4.96 out of 5 average rating, 23 reviews

Smoke and Pet Free, Washer Dryer, Balcony, Cozy

Guest favorite

A modern living area features a blue sofa accented by colorful pillows. A flat-screen TV is positioned on a white media console. A round coffee table sits on a textured area rug, with plants adding a touch of greenery. The open kitchen is visible, showcasing light wood cabinetry.

Condo in Downers Grove

4.92 out of 5 average rating, 62 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.

A light-filled living area features a comfortable beige sofa adorned with decorative pillows. A coffee table sits in front, holding a plant and tray. In the background, a kitchen with wooden cabinets and bar stools is visible, complementing the modern aesthetic.

Condo in Downers Grove

4.87 out of 5 average rating, 54 reviews

Upscale, Smoke and Pet Free, Washer Dryer, Balcony

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 Penthouse 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, LED fireplace, and Netflix.

Guest favorite

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

4.94 out of 5 average rating, 16 reviews

Cozy & Relax Escape

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!

An aerial view of a large, two-story house showcases a well-maintained exterior with a symmetrical facade and a spacious driveway. Surrounding greenery enhances the property's appeal, while a glimpse of an above-ground pool is visible in the backyard.

Home in Bartlett

4.64 out of 5 average rating, 25 reviews

Fully Furnished Executive Home, Lux Amenities

MASTER BATHROOM IS UNDER RENOVATION AS OF 2/1/25- UNTIL 5/15/25!!! The Bartlett house was just updated and is a place that families and friends will truly enjoy. The kitchen is a chefs dream while the living room is huge with a great view of the park. The basement will entertain your group for hours with a movie theatre wall(4K TV’s) gym and massive fish tank! Bring the whole family to this great place with lots of room for fun! This is a pet friendly house!

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

4.61 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