10 Best Vacation Rentals With Private Pool In Chicago, Illinois - Updated 2024

Plarlene Juliane
Plarlene Juliane 
Updated
| 4 min read

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 March 02, 2024.

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.

Stayed at this property?

20.82 km (13.0 mi) from Henry A. Proesel Park Pavilion
11 reviews   Wifi Available
House 6 Guests 3 Bedrooms 1 Bathroom

Accommodates: 6
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
the pool was great the fire tables allowed us to stay outside in the evening make s'mores etc
the yard is large and really nice with the pool several seating areas and nice gardens
Host:
the owner be was very friendly and helpful
be was an amazing host and we can’t wait to come back
house was clean and be/host was great to work with
Read more reviews
Oops, this listing is currently inactive. Check out these alternative properties in the same location.
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

2. Well-kept home close to downtown

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.

Stayed at this property?

19.75 km (12.3 mi) from Henry A. Proesel Park Pavilion
1 review   Superhost Wifi Available
ENTIRE HOME 3 Beds 10 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 10

Top guest reviews
Location:
uber is accessible and you can find easily where to park your car and close to the house
we definitely recommend this as a great place to stay
Read more reviews

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.

Stayed at this property?
Chicago, Illinois, United States
8.5 km (5.3 mi) from Henry A. Proesel Park Pavilion
16 reviews   Superhost Wifi Available
Entire residential home 12 Beds 16 Guests 6 Bedrooms 5 Bathrooms

Accommodates: 16

Top guest reviews
Amenities & Room:
additionally the outdoor heated pool was perfect for the group to both relax and hangout in
the place is huge with plenty of space/beds for our group of 14
house has lots of fun features for the group too: pool game room roof deck
we especially loved the kitchen pool and outdoor space joe was so very responsive and helpful
Cleanliness:
the bathrooms were clean and they provided towels for us all
Host:
amazing place and outstanding host highly recommend
joe was very helpful and accommodating to our needs
joe was a model host and his house is beautiful and modern
joe is helpful with recommendations for catering and any other services we needed
joe was an excellent host that was very communicative and got the house in perfect shape for us
Location:
good location in wrigelyville
great location (easy walk to wrigley)
everything we needed was in the house and location is perfect
the house is fantastic and in a great location
Read more reviews

Nearby vacation rentals with private pool

4. Remodeled vacation home with bay views (from USD 828)

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.

Stayed at this property?
Johnsburg, Illinois, United States
56.22 km (35.0 mi) from Henry A. Proesel Park Pavilion
49 reviews   Wifi Available
ENTIRE HOME 10 Beds 16 Guests 4 Bedrooms 4 Bathrooms

Accommodates: 16

Top guest reviews
Amenities & Room:
there were many amenities and the kitchen was better stocked than i anticipated
the bedroom/bathroom set up is perfect
top amenities: comfy beds amazing pool prime lakefront location views from main living room
Cleanliness:
the house was very clean and tidy
the house was fantastic very clean and everything we needed was on site
we had a fantastic weekend getaway the house was clean and the perfect space for us
brand new beds in every room and everything was very clean
great view clean and host responds quickly
Host:
was an amazing host who responded quickly
jj is an excellent host
great space and amazing host will definitely look to book again during the summer
Location:
perfect city getaway for a family looking for something close but feels far away
i would definitely reccomend the location for parties of 10 or more
definitely a place to come back place very nice and is perfect for big families or large groups
Read more reviews

5. Casa Dra’eh (from USD 470)

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.

Stayed at this property?
Plainfield, Illinois, United States
63.43 km (39.5 mi) from Henry A. Proesel Park Pavilion
61 reviews   Superhost Wifi Available
ENTIRE HOME 3 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
a great view a cozy space and a wonderful time
huge backyard and in ground pool
the house had aa amazing kitchen and the couches were plus and comfortable
Host:
the house is lovely and the hosts are excellent
i highly recommend this property and hosts
such a beautiful glamorous home’ the owner’s were very kind’ responsive’ and helpful
our airbnb stay here was fantastic daniel was extremely responsive and attentive
would highly recommend hosts were extremely helpful throughout entire stay and the house is beautiful
Location:
awesome home great location great communication
Read more reviews

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.

Stayed at this property?

10.25 km (6.4 mi) from Henry A. Proesel Park Pavilion
9 reviews   Wifi Available
House 7 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 7
Minimum Nights: 25
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Cleanliness:
the house was absolutely beautiful and immaculately clean
Host:
the owners were incredibly responsive
the notes left by the owners were open and inviting with only respectful common sense requests
our rental was very nice and the manager was helpful with any needs that arose during our stay
we had everything we needed and communication with the owner was quick and easy
Location:
my son loved playing in the pool and my family loved the location
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

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.

Stayed at this property?

893 meters (0.6 ft) from Henry A. Proesel Park Pavilion
10 reviews   Wifi Available
ENTIRE HOME 4 Beds 12 Guests 4 Bedrooms 4 Bathrooms

Accommodates: 12

Top guest reviews
Cleanliness:
nice clean n breath taken house it was the most amazing stay i’ve ever had
extremely happy with the cleanliness of the house and amenities
Host:
the hosts were very friendly and great people and so easy to work with
our stay was fantastic the hosts were very accommodating and responsive
they were very responsive and addressed any concerns that we had promptly with absolute professionalism
Location:
highly recommend for the location close to expressway and easy to navigate to downtown
Read more reviews

8. Charming mansion with an excellent location (from USD 1299)

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.

Stayed at this property?
Naperville, Illinois, United States
53.49 km (33.3 mi) from Henry A. Proesel Park Pavilion
9 reviews   Wifi Available
ENTIRE HOME 6 Beds 12 Guests 6 Bedrooms 3 Bathrooms

Accommodates: 12

Top guest reviews
Location:
this is the best place to book will definitely be booking again soon
Read more reviews

9. Well-furnished home in a quiet location (from USD 770)

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.

Stayed at this property?
Grayslake, Illinois, United States
45.38 km (28.2 mi) from Henry A. Proesel Park Pavilion
109 reviews   Superhost Wifi Available
ENTIRE HOME 11 Beds 16 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 16

Top guest reviews
Amenities & Room:
the pool and theater were everyone's favorites
thank you namestay we had a blast in the pool and loved the property
there was room to spread out and we had plenty of fun things to do
we had a wonderful stay at this beautiful pool house
Cleanliness:
very clean and maintained
the pool was very clean and the temperature was perfect
everything was as described and very clean
the rooms were comfortable and clean
the house was very clean and welcoming even our name on the board in the front foyer
Host:
they were also super responsive throughout the weekend with any questions we had
the host laid this home out to feel very cozy and we definitely enjoyed it
lauren and zeke was very responsive and friendly
Location:
my family enjoyed every minute at this location
convenient location near local forest preserves for some great hikes
very nice quiet neighborhood for a relaxing time
Read more reviews

10. Opulent villa for eight (from USD 125)

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.

Stayed at this property?
Olympia Fields, Illinois, United States
54.52 km (33.9 mi) from Henry A. Proesel Park Pavilion
29 reviews   Wifi Available
ENTIRE HOME 4 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
the pool and outside areas were very enjoyable though
Cleanliness:
place was clean and comfortable
it was clean and he was very courteous
Host:
the hosts were very helpful and had a quick response time to everything
this house was great the host was friendly and his response was quick whenever he received our text
Location:
i recommend this place
Read more reviews

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.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

History


Get Trip101 in your inbox

Unsubscribe in one click. See our Privacy Policy for more information on how we use your data

Plarlene manages a personal blog at www.plarlenejulianev.tumblr.com. She has also committed to traveling to various Asian countries, specifically Malaysia, Singapore, Thailand, Hong Kong, and...Read more

 Want to contribute as a Local Expert?
Explore Chicago
x
Good things are meant to be shared!
Back to top
Visited any of these places? Click this button to activate our "Add a Tip" feature to share your experience.