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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Superhost

The resort is showcased against a backdrop of the Caribbean Sea and a clear sky. Lush palm trees frame the pool area, which features lounge chairs arranged around sparkling waters. The contemporary architecture of the building complements the tranquil beach setting.

Home in Itasca

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

Guest favorite

A spacious living area is featured, highlighted by a neutral palette and large windows with blinds allowing natural light. A stone fireplace serves as a focal point, complemented by white sofas and an ornate coffee table. A television is mounted above the fireplace for entertainment.

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 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.

Superhost

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.

Apartment in Warrenville

New place to stay

Naperville Escape 2BR - Pool, Gym & Pickleball!

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!

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.

Apartment in Lombard

4.75 out of 5 average rating, 16 reviews

Smoke and Pet Free, Washer Dryer, Wood Fireplace

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.

A cozy living area features a comfortable gray sectional sofa and a round coffee table with plants and decorative items. Behind, a dining space with a table for four is visible, along with framed artwork on the walls and a large round mirror. Light floods the space.

Apartment in Lombard

4.74 out of 5 average rating, 34 reviews

Balcony, Pond View, Washer Dryer, Smoke Free

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

4.86 out of 5 average rating, 21 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 favorite

The backyard features an above-ground pool surrounded by lush greenery. A sandy play area is visible, equipped with colorful toys and vehicles. Comfortable lounge chairs are positioned nearby, creating a relaxed outdoor space perfect for leisure and play.

Home in West Chicago

5 out of 5 average rating, 6 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!

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

Guest favorite

A spacious basement game area features a classic pool table with a vibrant green felt surface, complemented by cues and an arranged set of colored balls. Nearby, a seating area with leather couches and an arcade machine is visible along the wooden-paneled wall.

Home in Bloomingdale

4.92 out of 5 average rating, 51 reviews

Now Open: Heated Pool with Entire House

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, plenty of room. Plus, unwind with a game of pool on the basement's pool table. High-speed internet keeps you connected. Hot Tub open! Swimming Pool closed until May.