Vacation rentals with a pool in DuPage County

Find and book unique homes with a pool on Airbnb

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Popular amenities for DuPage County rentals with a pool

House rentals with a pool

Guest favorite
Home in Highland Park
4.92 out of 5 average rating, 142 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

JeffRating, 5 stars4 months ago
We were in town for Thanksgiving visiting family with our dogs for 4 nights. Communication with host was great. The house was very clean, well furnished (we cooked the Thanksgiving meal there), recently renovated kitchen (huge kitchen island) with high end appliances, and yes there are 6 bedrooms (some small but nice). Rooms are split between three floors so everyone had room/privacy. Backyard with pool was great, lots of space for dogs, everything is fenced in but the front which was not a problem as the house is on a dead-end street with very little traffic. This is definitely a superhost home, all your condiments, lots of nice touches and snacks/gifts. We will definitely stay there again on our next visit to family in Chicago. House is locate between 41 and 94 making travel around Chicago easy.
A sparkling saltwater swimming pool is featured, surrounded by a textured concrete deck. The pool's clear blue water reflects light, and the edge is lined with a decorative coping. Shade from nearby trees creates playful patterns on the pool's surface.
Home in Olympia Fields
4.56 out of 5 average rating, 43 reviews

Luxurious South Suburban Villa

LanceRating, 5 stars2 months ago
My team thanks you for your comfortable home, it is what the crew needs after a day working outside on a large solar field array. Whenever on an extended out of town work trip we like to stay at an Airbnb, a much better value than several rooms at hotels. Your home was roomy & comfortable, we enjoyed our stay and thank you for being a great host.
A single-story house is set against a backdrop of trees, featuring a stone facade and a sloped roof. A winding driveway leads to a two-car garage on the right. Lush green grass surrounds the home, contributing to a serene environment.
Home in Lockport
4.63 out of 5 average rating, 8 reviews

Hidden GEM OASIS in Chicagoland

Raymond BrianRating, 5 stars3 weeks ago
Excellent host! Fantastic property!
The exterior of a three-story townhome is presented, featuring light-colored siding and a brick accent. A single-car garage is visible, along with a small front lawn. Large windows allow natural light to enter, while a tree branch extends above, casting gentle shadows.
Home in Schaumburg
4.71 out of 5 average rating, 7 reviews

Spacious 3 Floor Townhome

MelissaRating, 5 stars2 weeks ago
This spot is awesome. Close to the mall and lots of places to eat and things to do. Very spacious tri level. Free Parking on premises. Lots of room for people to sleep very spacious. Comfy couches. The bed I had was great. Our venue was very close for the event we attended we will be back!
The dining area features a rustic wooden table surrounded by dark chairs, complemented by a contemporary light fixture above. A decorative shelf displays various items, and a cozy seating area with a couch and chair can be seen in the background, illuminated by natural light.
Home in Plainfield
4.7 out of 5 average rating, 37 reviews

30 mins to CHI |3 Kings | Fireplace|W/D|Workspace

Demetrianna RRating, 5 stars7 months ago
The place was absolutely beautiful. Very clean and smelled so good. The house itself was gorgeous. The outdoors area was what made us book and it looked even better in person.
Guest favorite
Home in Schaumburg
4.91 out of 5 average rating, 22 reviews

Schaumburg Oasis with a Pool and Hidden Garden

GotimukulRating, 5 stars2 weeks ago
had such a wonderful stay! The place was exactly as described—clean, cozy, and beautifully maintained. The host was incredibly kind and responsive, making the whole experience smooth and stress-free. Would definitely stay here again and highly recommend it to anyone looking for a comfortable and welcoming place to stay!
Guest favorite
A modern hallway features arched openings along white walls, accented by warm lighting that highlights the dark wood flooring. Dark doors are positioned at either end, providing a clean and sophisticated look.
Home in Plainfield
4.93 out of 5 average rating, 75 reviews

Relaxing Spanish style Home (w/inground pool)

DevonRating, 5 stars7 months ago
House was lovely. I enjoyed the homes decor. Every day I woke up with something else I loved. The house had everything we needed. Only thing I wished the pool heater was working and the pillows were flat. I would definitely stay here again.
Guest favorite
A backyard patio is softly lit by string lights, casting a warm glow across the outdoor space. Paved stones create a welcoming area, surrounded by greenery. Steps lead to a raised wooden deck, enhancing accessibility and inviting outdoor gatherings.
Home in Elgin
4.86 out of 5 average rating, 14 reviews

$10 Cleaning Fee Promo! - Home in Elgin

JordanRating, 5 stars3 weeks ago
The pictures are very accurate, with 3 bedrooms the house is roomy. Private fenced yard, perfect for evenings relaxing. Easy check-in and very responsive hosts. Good neighborhood location, good water pressure, and comfy bed.

Condo rentals with a pool

Guest favorite
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, 93 reviews

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

SeanRating, 5 stars1 week ago
Really great place with lots to do nearby!
Guest favorite
Condo in Evanston
4.96 out of 5 average rating, 104 reviews

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

JasonRating, 5 stars5 days ago
Our stay in Evanston was great! The apartment is close to all of downtown Evanston, the Metra, and the L. Also easy access to NU. Everything was just as it says and the free underground parking is a HUGE plus!
Guest favorite
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
4.94 out of 5 average rating, 85 reviews

Just remodeled apartment close to airport and mall

MeagRating, 5 stars1 month ago
I am incredibly particular with places I stay. This place was simple, very clean, had everything you would need to be comfortable. Bed was great! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️
Guest favorite
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, 124 reviews

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

NinaRating, 5 stars1 month ago
We had a great stay at Michelle’s “Heart of Evanston.” I loved the indoor garage parking option with easy in and out. If you have a large vehicle /SUV, maneuvering in and out of the spot may be challenging depending if the spot over is occupied. We have a mid-size SUV and had no issues. The room was easily accessed from the garage and we had no issues getting in. The place was clean and well organized. I loved that it smelled clean and also had a faint hint of bleach in the bathroom. It was a little warm in the bedrooms at night but we used the air conditioning to bring the temperature down. Town is very walkable and we enjoyed the local restaurants (Taco Diablo, Bat 17, Bennison’s bakery). We found the town to be very quiet - almost too quiet for what we expected but after our visit to Northwestern found out it was spring break for the students. Michelle was available for any questions and always replied promptly. We had a great stay and would stay again!
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, 45 reviews

Pond View, Washer Dryer, Non Smoking Community

CalebRating, 5 stars6 months ago
I stayed here while traveling for work. It was comfortable and cozy. This is a perfect place to choose for extended stays. Great location, I would recommend.
Guest favorite
Condo in Evanston
4.96 out of 5 average rating, 97 reviews

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

JohnRating, 5 stars4 weeks ago
We really enjoyed staying at Michelle's place. It was a perfect home away from home while visiting Northwestern University. The area had many cafes and restaurants. The place was spacious with three bedrooms and two bathrooms. The primary suite had a very firm mattress. But this did not bother us at all. The kitchen was well stocked with pots, pans, glasses, plates and utensils. There's a coffee maker and we were able to try some local coffees in the area. We enjoyed having family dinners on the bar style, raised table and stools. The view of the sunset from the balcony was amazing each night with purples, pinks and trees - fantastic views of Evanston. The place is great for watching movies with a long couch lounger, cozy seats and cup holders! The area is a perfect blend of city and nature with Lake Michigan nearby. We will definitely be back.
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
4.93 out of 5 average rating, 46 reviews

Pond View, Washer Dryer, Non Smoking, Pet Free

Moua ShouaRating, 5 stars2 months ago
Our stay was lovely. The unit was clean, and it had everything we needed. Instructions on how to get in were clear, and if I had any questions Briana promptly responded. If/when we visit Lombard again, we'll keep this airbnb in mind.
Guest favorite
Condo in Evanston
4.96 out of 5 average rating, 113 reviews

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

XavierRating, 5 stars1 week ago
Great place to stay if you visit your daughter or son at Northwestern. The apartment is modern, clean, comfortable, super quiet, walkable distance from commodities. The communication with Mihyun was flawlessly, proactive, helpful. She offered flexibility on check in/out time as well as responsive advice on the surroundings. Thank you, Michelle

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