Vacation rentals with a pool in DuPage County

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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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Townhouse in Warrenville

New place to stay

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!

Jan 5 – 12

R4,783 ZAR per night

Apartment in Villa Park

5.0 out of 5 average rating, 3 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.

Sep 15 – 22

R2,466 ZAR per night

Home in Lisle

Welcoming, cozy, and a fur baby paradise.

Relax with the whole family at this peaceful place to stay, including your fur babies! 3 bedroom, one bath. Bedrooms are currently getting furnished, bedroom photos will be on site once furniture is set. We offer a pet heaven, fully fenced back yard with nearly 3/4 acre of running room. House is simply lovely but the chance to bring your fur babies is the place to be! Above ground pool for the warmer months is so much fun! We will help make your stay a great one. Near Naperville and Aurora.

Nov 10 – 17

R6,331 ZAR per night

Guest favorite

Condo in Lisle

4.95 out of 5 average rating, 42 reviews

Peaceful Condo in Lisle, Illinois

Quiet condo with balcony overlocking the forest located in Lisle. Minutes from I-88, I-355, Commuter train goes directly to Chicago, Benedictine University , North Central College , Wheaton College. Shopping, movie, restaurant are walking distance. Access to pool , Lake , fishing, disc golf, canoes, tennis court, volleyball, walking paths, ski and snowboard hill, Restaurant/ pub with live music and entertainment, Convenience store. Discounts for weekly bookings longer stays over 28 days.

Mar 25 – Apr 1

R1,490 ZAR per night

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.

Jul 18 – 25

R13,632 ZAR per night

Superhost

Apartment in Lisle

4.65 out of 5 average rating, 78 reviews

Tranquility and comfort in private condo

This unique condo has a private entrance and backs to a stunning lake! Come relax in this stylish Boho decor place with 2 large bedrooms with high-end mattresses and 2 full bathrooms. Wake up to your comforting hot coffee from the Nespresso machine. Then sit and enjoy the lake view from your patio on the rocking chair next to a cozy warm fire. Four lakes features walking paths, ski hills, and sledding. Located close to grocery store, restaurants, and a close 30 min to downtown or airport.

Aug 11 – 18

R3,911 ZAR per night

Guest favorite

Home in Glen Ellyn

4.94 out of 5 average rating, 16 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

Jul 23 – 30

R9,648 ZAR per night

Guest favorite

Condo in Lombard

4.97 out of 5 average rating, 36 reviews

Pond View, Washer Dryer, Non Smoking, Pet Free

Our cozy condo is the ideal place to feel at home. Affordable, close to Downtown Chicago, Downers Grove, Wheaton, Oakbrook, shopping, dining, highways. there’s nothing better than this fully furnished unit. Recently renovated, includes everything you need from free parking, linens to dishes, cookware, cable, wireless internet, queen size bed, in-unit washer - dryer, smart TV’s, Alexa, basic cable, Netflix, Hulu . Relax on the balcony view of the pond and waterfall.

Dec 31 – Jan 7

R3,194 ZAR per night

Apartment in Naperville

4.6 out of 5 average rating, 20 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

Sep 27 – Oct 4

R3,321 ZAR per night

Superhost

Apartment in Lombard

4.86 out of 5 average rating, 37 reviews

Balcony, Pond View, Washer Dryer, Non Smoking

Welcome to our cozy retreat with pond and waterfall views! Fully furnished for comfort, our prime location near Downers Grove, Wheaton, Oakbrook, and Downtown Chicago offers free parking, washer-dryer, dishwasher, and amenities like linens, dishes, cookware, cable, Wi-Fi, queen-size beds, smart TV, and Hulu. Experience a delightful stay, perfect for business or leisure, with little touches that make you feel at home. Long-term stays welcome!

Jul 29 – Aug 5

R3,415 ZAR per night

Home in Carol Stream

4.55 out of 5 average rating, 20 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.

Nov 11 – 18

R5,869 ZAR per night

Home in West Chicago

Cozy & Specious 1 bedroom lower level Apt

Lower Level private entrance apartment has w 1 bedroom/bathroom, living room, kitchenette. Access to the patio & seasonal pool. Keyless entry. 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.

Jul 17 – 24

R2,527 ZAR per night