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Photograph: Courtesy Brian Di Bartolomeo

The best Airbnbs with pools near Chicago

Whether you prefer lakeside villas or tiki bar hideaways, these Airbnbs with pools will help you stay cool this summer

Written by
Emma Krupp
Rosemary Waugh
Alex Floyd-Douglass

When the Chicago summer kicks in, the mercury starts to rise and the humidity reaches its sticky heights, there’s one thing on every Chicagoan’s mind: to get in some water and cool down as soon as humanly possible. And sure, Chicago’s finest beaches are always worth a visit, but sometimes nothing quite beats a sumptuous dip in a beautiful private pool.

Enter Airbnb, which has positively bucketloads of rentals with swimming pools within a few hours of Chicago. From forested backyard oases to indoor spa pools, here are six of the best pool-equipped Airbnbs perfect for beating the summer heat.

RECOMMENDED: Lakefront Airbnbs to rent for a summer getaway from Chicago

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Airbnbs with pools near Chicago

The decked out home in Grand Beach, MI
Photograph: Courtesy Bluefish Vacation Rentals

The decked out home in Grand Beach, MI

A sandy backyard area thronged by tall beach grass means you’ll have no trouble envisioning you’re waterside at this stately Michigan home, which also features a putting green and a hot tub on its premises. Bonus: the house is only two blocks from Lake Michigan’s shore if you feel like switching up your swimming routine.

The Green Bay vacation home in Allouez, WI
Photograph: Courtesy the host/Fotosold Photography

The Green Bay vacation home in Allouez, WI

Even in the summer, you can’t bank on the weather is great all the time – so sometimes you need an indoor pool too. This swanky lodge in Green Bay has a heated indoor pool that comes with a volleyball net. If you’re not the sporty type, the rental also has a poker table, massage chairs, a videogame corner, and plenty of flat-screen TVs.

The Italian country estate in Kankakee
Courtesy: Airbnb

The Italian country estate in Kankakee

Fancy a stay in a country estate? Now's your chance. This Chicago Airbnb complete with a stunning outdoor pool has all of your luxury needs covered. From a fully equipped open-plan kitchen and dining area to the well-positioned bedrooms with epic views, it's an ideal getaway for the whole family. The property can sleep up to eight guests comfortably while the manicured garden offers peace and tranquillity – especially if you've brought the kids along.

The Lake Mary cottage in Twin Lakes, WI
Photograph: Courtesy the host/Chris Kaiser Photography

The Lake Mary cottage in Twin Lakes, WI

This beautiful lakeside house can sleep up to 20 guests. So assemble your nearest and dearest, and head off for a long weekend or summer vacation to remember. Along with the heated private pool, visitors can while away the hours on the fishing pier or try out a range of watersports on the lake. It’s also a pretty sweet spot to simply kick back and relax in.

The private paradise in South Haven, MI
Photograph: Courtesy the host/Justin Maconochie

The private paradise in South Haven, MI

It’s not often you can apply the word "tropical" to something in southern Michigan, but this place fits the bill: A saltwater pool, sandy backyard, hammocks, colorful blooming flowers, and even a tiki bar (complete with multi-flavored vodkas and IPA on tap) work to create an almost island-like feel.

The coastal dream in Three Oaks, MI
Photograph: Courtesy Yellow Bird Vacations/Moguel Photography

The coastal dream in Three Oaks, MI

You’ll definitely want to take your morning coffee on the back deck of this southern Michigan gem, which sits perched on a wooded dune high above Lake Michigan. There’s a private beach below, but the sun-dappled pool – complete with a new deck and a cabana – makes for an especially tranquil place to take a dip.


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