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Brian Di Bartolomeo, Airbnb
Photograph: Courtesy Brian Di Bartolomeo

8 best Airbnbs with pools near Chicago well worth a dip

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

Written by
Emma Krupp
Contributors
Rosemary Waugh
,
Alex Floyd-Douglass
,
Camila Karalyte
&
Jennifer Banful
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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. Pass the lotion, will ya?

Enter Airbnb: with positively bucketloads of rentals with swimming pools within a few hours of Chicago. From forested backyard oases to indoor spa pools, here are the best pool-equipped Airbnbs perfect for beating the heat. Where's our invite?

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Who makes the cut? While we might not stay in every Airbnb featured, we've based our list on top reviews, hosts and amenities to find you the best stays. This article includes affiliate links. These links have no influence on our editorial content. For more information, see our affiliate guidelines.

Airbnbs with pools near Chicago

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

1. 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.

Rooms? Five bedrooms. Sleeps 14 guests. 
The mood? An old charmer. 
Location perks? The heated in-ground pool is accompanied by a hot tub, gas grill and a large outdoor dining area. 
Budget range? A moderately-priced group trip. 

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

2. 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.

Rooms? Six bedrooms. Sleeps 14 guests. 
The mood? Contemporary glam. 
Location perks? Perched on a hillside, this vacation home not only has gorgeous views, but a backyard, movie theatre and best of all, the pool stays warm all year round. 
Budget range? Top dollar quality time with the fam. 

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The luxury home in Highland Park, IL
Courtesy: Airbnb

3. The luxury home in Highland Park, IL

Big enough for an enormous group of friends or family (up to 15 guests, in fact), this luxury home Airbnb is perfect for your trip away from Chicago. With a huge backyard pool and BBQ area, you can soak up the rays in this Airbnb and you'll never want to leave. Luxurious, modern, and comfortable. 

Rooms? Six bedrooms. Sleeps 15 guests. 
The mood? Mini paradise. 
Location perks? Set on two private acres of lush greenery–that's more than enough room for hide and seek or a cute picnic. 
Budget range? Hefty, but decent when you split the cost.

The country getaway in Lakeville, IN
Courtesy: Airbnb

4. The country getaway in Lakeville, IN

Okay, we know it's giving Flintstones, but this rustic Airbnb has – in our opinion – the coolest swimming pool/pond combination within easy distance from Chicago. What's more, this is the ideal home for a large family looking for adventure. This epic home has seven bedrooms with a total of 15 beds – yes, 15 – and 2.5 bathrooms. Aside from the uber-cool rock-pool-style pond, there's a full basketball court, volleyball, pickleball, a trampoline, an outdoor kitchen, and a grill – oh, and there's a hot tub if that's more your vibe. Dive in.

Rooms? Seven bedrooms. Sleeps 16 or more.
The mood? A nostalgic family adventure.  
Location perks? Looking for a homely vibe? This one is situated at the end of a cul de sac so it feels safe and secluded.
Budget range? Surprisingly affordable when you spread the cost.

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The Italian country estate in Kankakee, IL
Courtesy: Airbnb

5. The Italian country estate in Kankakee, IL

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.

Rooms? Three bedrooms. Sleeps eight guests. 
The mood? Dreamy and antique. 
Location perks? Manicured landscapes, walking trails and biking paths. Bellisimo. 
Budget range? Not too shabby for a friend's trip or a family vacay.

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

6. The lakeside 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.

Rooms? Seven bedrooms. Sleeps 16 guests or more. 
The mood? Country chic. 
Location perks? Walking distance to Twin Lakes – kayaks, canoes and paddle boards are available for rental. 
Budget range? An exceptional location at affordable rates. 

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The lodge oasis in Saugatuck, MI
Photograph: Courtesy Brian Di Bartolomeo

7. The lodge oasis in Saugatuck, MI

On the edge of a forest and about a mile from the scenic beach town of Saugatuck, this ridiculously pretty hideaway boasts not just a magnificent, chaise longue-lined pool and an outdoor shower but its own private basketball court. The pool isn’t open year-round (it closes in October), but the hot tub certainly is.

Rooms? Three bedrooms. Sleeps 10 guests.
The mood? Cozy lodge house vibes. 
Location perks? A peaceful oasis with the coziest well-appointed rooms and private beach access on Silver Lake. 
Budget range? A luxury getaway. 

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

8. 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.

Rooms? Four bedrooms. Sleeps eight guests. 
The mood? A slice of Malibu.
Location perks? A stone's throw from downtown and Lake Michigan where you can enjoy bike tours, hiking, and of course, getting out on the water.
Budget range? Moderately priced for four-nights. 

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