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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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The exterior of a spacious two-story home is shown, featuring a mixture of brick and siding. Lush green landscaping surrounds the house, with trees casting shade across the front yard. A paved driveway leads to a garage, and a clear blue sky provides a bright backdrop.

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

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.

The living area features a modern design with a gray sofa adorned with yellow cushions, complemented by a round dining table with blue chairs. Bright natural light enters through sliding glass doors, leading to a small balcony, while artwork decorates the blue accent wall.

Apartment in Warrenville

New place to stay

Luxury 2BR - Pool, Gym, Mins to Naperville!

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 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

4.82 out of 5 average rating, 60 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.

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

4.76 out of 5 average rating, 17 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 room space features a comfortable sofa adorned with decorative pillows. A sleek coffee table sits atop a soft carpet, complemented by a green potted plant. Large sliding glass doors provide access to a private balcony, enhancing natural light in the area.

Apartment in Lombard

4.82 out of 5 average rating, 49 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.

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, 35 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.

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, 24 reviews

Smoke and Pet Free, Washer Dryer, Balcony, Cozy

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 comfortable living area features a dark sofa, coffee table, and a modern TV stand with a large television. A dedicated dining space with a round table for two is visible. Sliding glass doors lead to a private balcony, providing natural light and outdoor views.

Condo in Lombard

4.94 out of 5 average rating, 48 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.

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, 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.

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

4.89 out of 5 average rating, 9 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!

Vacation rentals for every style

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A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for DuPage County rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious living area is presented with a large, U-shaped sectional sofa and a matching armchair. A coffee table sits in the center, complemented by light hardwood floors and a patterned area rug. Natural light filters through a nearby dining space, featuring a table set for meals.

Home in Montgomery

5 out of 5 average rating, 7 reviews

5 bdrm/2.5 bth/Fenced Yard/Quiet St /Pet friendly

A living room is presented with light wooden flooring and a soothing grey wall. Two red sofas are arranged for seating, facing a wall-mounted television. Natural light filters through two textured window shades, and a lamp stands beside the furnishings, adding to the room's cozy layout.

Home in Schaumburg

4.8 out of 5 average rating, 20 reviews

Spacious 3 Floor Townhome

An expansive outdoor space showcases a landscaped backyard with an in-ground pool, surrounded by a protective fence. Loungers are positioned around the pool, and a covered seating area is visible, providing shaded relaxation options. Nearby, a well-maintained lawn extends into the background.

Home in Plainfield

4.76 out of 5 average rating, 46 reviews

30 mins to CHI• 3 Kings• BBQ Grill• Spacious• Pool

4.5 out of 5 average rating, 6 reviews

Hacjenda

A spacious backyard is illuminated by soft evening light, showcasing a lush green lawn framed by well-maintained gardens. Multiple seating areas are visible, including a hammock, lounge chairs, and patio furniture. A large tree offers shade, while a pool is partially seen beyond the greenery.

Home in Schaumburg

4.94 out of 5 average rating, 33 reviews

Schaumburg Oasis:Private Pool & Enchanted Garden

A modern kitchen is showcased with sleek white cabinetry and stainless steel appliances. An island with bar seating is positioned in the foreground, while a spacious archway leads to an elegantly designed hallway featuring artwork and natural light.

Home in Plainfield

4.94 out of 5 average rating, 80 reviews

Relaxing Spanish style Home (w/inground pool)

A fenced-in backyard features a landscaped yard with well-maintained grass surrounding a heated in-ground pool. The pool area includes a comfortable covered patio, providing shade with ample space for relaxation. Lush green trees and shrubs create a serene atmosphere.

Home in Crystal Lake

5 out of 5 average rating, 10 reviews

In Ground Pool, Full Ranch Home

The exterior of a mid-century modern ranch home is displayed, featuring a flat roof and a large, contemporary garage door. Lush greenery surrounds the entrance, complemented by a well-maintained lawn. The driveway provides ample space for parking, enhancing accessibility.

New place to stay

Luxury fenced in modern ranch

Condo rentals with a pool

An outdoor pool area is shown, featuring a clear blue pool surrounded by lounge chairs. Trees provide a touch of greenery, while a modern glass structure offers shaded seating. Sunshine reflects off the water, creating a bright and inviting atmosphere.

Condo in Evanston

4.96 out of 5 average rating, 98 reviews

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

Condo in Evanston

4.95 out of 5 average rating, 111 reviews

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

The living area features a comfortable gray sofa facing a modern TV stand. A light rug lies beneath a white coffee table adorned with a small plant. Natural light filters through a large window, complemented by soft curtains. A desk and chair are positioned in the corner.

Condo in Elk Grove Village

4.93 out of 5 average rating, 87 reviews

Just remodeled apartment close to airport and mall

An outdoor swimming pool is surrounded by lounge chairs, offering a relaxing space. Trees are strategically placed around the area, and large glass walls provide views to the inside. Sunlight reflects off the water, enhancing the serene setting.

Condo in Evanston

4.91 out of 5 average rating, 128 reviews

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

Condo in Evanston

4.96 out of 5 average rating, 104 reviews

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

A modern living area is revealed with large windows showcasing views of the lake and boats. A light-colored sofa and armchair are arranged around a glass coffee table, complemented by a floor lamp and a large TV mounted against a neutral wall.

Condo in Burbank

Iconic Style, Charming Lake View

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, 55 reviews

Upscale, Smoke and Pet Free, Washer Dryer, Balcony

Condo in Evanston

4.96 out of 5 average rating, 120 reviews

Harmony of Evanston 1 BDR Exec Suite w/pool & Gym

Other vacation rentals with a pool

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

4.82 out of 5 average rating, 60 reviews

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

Top 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

4.93 out of 5 average rating, 55 reviews

Now Open: Heated Pool with Entire House

A cozy living area features a sectional sofa adorned with pillows and a throw pillow inscribed with 'Enjoy.' A round coffee table holds decorative items, while framed art showcases serene designs on the wall. A small dining area is visible in the background.

Condo in Lombard

4.91 out of 5 average rating, 47 reviews

Pond View, Washer Dryer, Non Smoking Community

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

4.76 out of 5 average rating, 17 reviews

Smoke and Pet Free, Washer Dryer, Wood Fireplace

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, 55 reviews

Upscale, Smoke and Pet Free, Washer Dryer, Balcony

A cozy living room space features a comfortable sofa adorned with decorative pillows. A sleek coffee table sits atop a soft carpet, complemented by a green potted plant. Large sliding glass doors provide access to a private balcony, enhancing natural light in the area.

Apartment in Lombard

4.82 out of 5 average rating, 49 reviews

Balcony, Pond View, Washer Dryer, Non Smoking

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, 35 reviews

Balcony, Pond View, Washer Dryer, Smoke Free

A comfortable living area features a dark sofa, coffee table, and a modern TV stand with a large television. A dedicated dining space with a round table for two is visible. Sliding glass doors lead to a private balcony, providing natural light and outdoor views.

Condo in Lombard

4.94 out of 5 average rating, 48 reviews

Pond View, Washer Dryer, Non Smoking, Pet Free

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