Picturesque buildings, award-winning museums, and lively entertainment scene are some of the best things you’ll see on your trip to Chicago. But that’s not all—this city is also a great place for art enthusiasts and foodies to explore. Here, you’ll get to visit a number of art galleries showcasing traditional and modern local art, such as The Art Institute of Chicago and the Museum of Contemporary Art. Do not leave the city without tasting Chicago-style pizza pies and hotdogs. After exploring this urban destination, you would need to stay in a place where you can relax and unwind. Check out the best vacation rentals with private pool in Chicago, Illinois.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to private pool. The image galleries get refreshed with the latest updates regularly. They were last updated on December 18, 2024.
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1. Stylish guest house in the heart of Chicago
This vacation rental for eight is ideal for a family getaway. If you’re visiting Chicago between May and September, feel free to take a plunge in the property’s private pool. This is ideal for cooling off and beating the summer heat.
This rental also offers everything you’ll need for a comfortable stay, including a full bathroom, a well-stocked kitchen, air conditioning, and a heating system. Dining, shopping, and outdoor activities are all within walking distance of the property.
20.82 km (13.0 mi) from Henry A. Proesel Park PavilionAccommodates: 6
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 30 days before check-in.
Top guest reviews
Host:
the owner be was very friendly and helpfulbe was an amazing host and we can’t wait to come backhouse was clean and be/host was great to work withRead more reviewsAmenities & Room:
the pool was great the fire tables allowed us to stay outside in the evening make s'mores etcthe yard is large and really nice with the pool several seating areas and nice gardens
2. Well-kept home close to downtown (from USD 667)
This wonderful residential property is an ideal holiday home for you and your family or group of friends. It is near downtown, where you can find the finest shops and restaurants in Chicago. The rental can sleep up to ten people, offering two bedrooms and two bathrooms.
An outdoor dining area, free WiFi, a television, and more are all part of your booking rate. There is a private pool area for you to indulge in a late-night swim. Note that the pool is only open from June to mid-September.
Top guest reviews
Read more reviewsLocation:
uber is accessible and you can find easily where to park your car and close to the housewe definitely recommend this as a great place to stay
3. Wrigleyville Mansion
This exquisite and beautifully appointed property has a lot to offer, including a convenient location. Venues for dining and shopping experiences are easily accessible from the property because it is only 15 minutes of driving to the downtown area. The exterior appears like an old-fashioned Chicago house, while the inside is arranged in a typical urban and chic home. It offers six bedrooms to fit sixteen guests.
For relaxation, there’s a fenced-in back garden with beautiful plants where you can stretch in the morning. You can also swim or play water volleyball in the property’s private pool.
Chicago, Illinois, United States
8.5 km (5.3 mi) from Henry A. Proesel Park PavilionSuperhost
Accommodates: 16
Top guest reviews
Host:
amazing place and outstanding host highly recommendjoe was very helpful and accommodating to our needsjoe was a model host and his house is beautiful and modernjoe is helpful with recommendations for catering and any other services we neededjoe was an excellent host that was very communicative and got the house in perfect shape for usLocation:
good location in wrigelyvillegreat location (easy walk to wrigley)everything we needed was in the house and location is perfectthe house is fantastic and in a great locationCleanliness:
the bathrooms were clean and they provided towels for us allRead more reviewsAmenities & Room:
additionally the outdoor heated pool was perfect for the group to both relax and hangout inthe place is huge with plenty of space/beds for our group of 14house has lots of fun features for the group too: pool game room roof deckwe especially loved the kitchen pool and outdoor space joe was so very responsive and helpful
Nearby vacation rentals with private pool
4. Remodeled vacation home with bay views (from USD 2280)
The Pistakee Bay is visible from the back of this house, offering guests a peaceful stay. The property is ideal for groups of up to sixteen members, and it comes with four spacious bedrooms with a total of ten beds.
You may relish your meals in the outdoor sitting areas while taking in the lush surroundings. If you’re staying with kids, they can have fun playing some board games while you cool down in the outdoor private pool. Note that the heated pool is only available between mid-May and September.
Top guest reviews
Host:
was an amazing host who responded quicklyjj is an excellent hostgreat space and amazing host will definitely look to book again during the summerLocation:
perfect city getaway for a family looking for something close but feels far awayi would definitely reccomend the location for parties of 10 or moredefinitely a place to come back place very nice and is perfect for big families or large groupsCleanliness:
the house was very clean and tidythe house was fantastic very clean and everything we needed was on sitewe had a fantastic weekend getaway the house was clean and the perfect space for usbrand new beds in every room and everything was very cleangreat view clean and host responds quicklyRead more reviewsAmenities & Room:
there were many amenities and the kitchen was better stocked than i anticipatedthe bedroom/bathroom set up is perfecttop amenities: comfy beds amazing pool prime lakefront location views from main living room
5. Casa Dra’eh (from USD 399)
Casa Dra'eh features an expansive backyard where you can access a private pool, perfect for a soothing afternoon or nighttime plunge. The property has three bedrooms and can comfortably accommodate eight guests. You may prepare your favorite meals in the well-stocked chef’s kitchen.
To keep yourself entertained while staying indoors, you can use the free WiFi, watch television, or play video games.
Top guest reviews
Host:
the house is lovely and the hosts are excellenti highly recommend this property and hostssuch a beautiful glamorous home’ the owner’s were very kind’ responsive’ and helpfulour airbnb stay here was fantastic daniel was extremely responsive and attentivewould highly recommend hosts were extremely helpful throughout entire stay and the house is beautifulLocation:
awesome home great location great communicationRead more reviewsAmenities & Room:
a great view a cozy space and a wonderful timehuge backyard and in ground poolthe house had aa amazing kitchen and the couches were plus and comfortable
6. Stylish vacation rental with in-ground pool (from USD 375)
Located in Glenview and only a 20-minute drive to downtown Chicago, this house offers spacious rooms, a well-equipped kitchen, and common indoor and outdoor spaces. It can accommodate seven guests in four bedrooms.
Feel free to swim laps in the in-ground heated pool or curl up with a nice book on the sun loungers. The pool features a shallow end and a diving board on the other side. You may also explore the nearby walking and biking trails.
Top guest reviews
Host:
the owners were incredibly responsivethe notes left by the owners were open and inviting with only respectful common sense requestsour rental was very nice and the manager was helpful with any needs that arose during our staywe had everything we needed and communication with the owner was quick and easyLocation:
my son loved playing in the pool and my family loved the locationRead more reviewsCleanliness:
the house was absolutely beautiful and immaculately clean
7. Vintage but elegant home with an indoor pool
Once you enter this vintage vacation home, you’ll feel like you’ve stepped back in time to the 1950s. This rental is ideal for those who love luxury because it has plenty to offer, starting with an indoor heated pool. An airy patio with barbecue facilities is accessible from the pool area.
Up to twelve guests can fit in this four-bedroom property. Other amenities include laundry equipment, WiFi, and a private hot tub. If you’re staying longer and you need to work remotely, there’s a dedicated workspace with a comfy chair that you can use.
893 meters (0.6 ft) from Henry A. Proesel Park PavilionAccommodates: 12
Top guest reviews
Host:
the hosts were very friendly and great people and so easy to work withour stay was fantastic the hosts were very accommodating and responsivethey were very responsive and addressed any concerns that we had promptly with absolute professionalismLocation:
highly recommend for the location close to expressway and easy to navigate to downtownRead more reviewsCleanliness:
nice clean n breath taken house it was the most amazing stay i’ve ever hadextremely happy with the cleanliness of the house and amenities
8. Charming mansion with an excellent location
When you stay at this mansion near downtown Chicago, you’re giving yourself a chance to enjoy a restful and memorable vacation. With six bedrooms, up to twelve guests can comfortably sleep here. There are three-and-a-half baths, a large living room with a flat-screen television and sectional sofa, and a full kitchen at your disposal.
An outdoor pool in the fenced yard is available to guests for a relaxing swim throughout their stay. Near the pool are a large barbecue grill and outdoor seating.
Naperville, Illinois, United States
53.49 km (33.3 mi) from Henry A. Proesel Park PavilionAccommodates: 12
Top guest reviews
Read more reviewsLocation:
this is the best place to book will definitely be booking again soon
9. Well-furnished home in a quiet location
This vacation rental is perfect for a memorable family getaway because it comes with a private theater and a huge indoor pool. The pool depth starts at 3.5 ft (1 m), and the deep end measures 10 ft (3 m). The property also has a living room next to a dining area and a kitchen with top-of-the-line equipment, great for whipping up sumptuous dishes for your loved ones.
The property comes with four bedrooms and ten beds, accommodating sixteen guests. Restful nights are guaranteed because this house is nestled in a quiet and private property. Located in Grayslake, this property is just an hour’s drive from Chicago.
Grayslake, Illinois, United States
45.38 km (28.2 mi) from Henry A. Proesel Park PavilionAccommodates: 16
Top guest reviews
Host:
they were also super responsive throughout the weekend with any questions we hadthe host laid this home out to feel very cozy and we definitely enjoyed itlauren and zeke was very responsive and friendlyLocation:
my family enjoyed every minute at this locationconvenient location near local forest preserves for some great hikesvery nice quiet neighborhood for a relaxing timeCleanliness:
very clean and maintainedthe pool was very clean and the temperature was perfecteverything was as described and very cleanthe rooms were comfortable and cleanthe house was very clean and welcoming even our name on the board in the front foyerRead more reviewsAmenities & Room:
the pool and theater were everyone's favoritesthank you namestay we had a blast in the pool and loved the propertythere was room to spread out and we had plenty of fun things to dowe had a wonderful stay at this beautiful pool house
10. Opulent villa for eight (from USD 215)
This villa is elegantly furnished with modern furniture and hardwood flooring. The property’s neat interior mirrors the beauty of the outside space surrounded by trees. It also features an outdoor heated pool. Use the poolside furniture to unwind between laps and appreciate the warmth of the sun.
Other amenities include WiFi access, television, bathroom essentials, and laundry equipment. The property is good for eight guests, offering three bedrooms and two-and-a-half baths.
Top guest reviews
Host:
the hosts were very helpful and had a quick response time to everythingthis house was great the host was friendly and his response was quick whenever he received our textLocation:
i recommend this placeRead more reviewsAmenities & Room:
the pool and outside areas were very enjoyable though
Relax when in Chicago
Whether it’s summertime or not, nothing beats a cool swim to re-energize yourself. When you take a trip to Chicago, opt for accommodation with a swimming pool. Find the perfect place to stay with our list of the best vacation rentals with private pool in Chicago, Illinois.
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