10 Family-Friendly Chicago Airbnb Rentals With Epic Pools

No need to book a family vacation to faraway destinations this summer, because that’s the time of year we live in as Chicagoans. The temperatures are perfect, the activities are plentiful and the scenery is magnificent. If you want to get away from your own four walls, turn to Airbnb. From skyscrapers in Chicago to mini-trips to farms with chickens, you can pick up an Airbnb rental that has a pool and fun, family-friendly amenities. Scroll through our list to start planning!

photo: Airbnb

This renovated 5-bedroom farmhouse in Lake Forest is a great option for extended families who want to spend quality time together. It is a stone’s throw from a public golf course, downtown Lake Forest is only a mile and a half, and a beach sand boardwalk is just two miles away.

Accommodation capacity : 9
Cost: $ 500 / night
In line: airbnb.com

photo: Airbnb

This 2019 built 5-bedroom stunner will make you feel like stepping back in time with sunken sinks, a claw-foot tub, distressed floors, and cedar beams, but it features modern touches and amenities throughout. The Galien River swamp is across the street and there are several bikes on site for cruising. Which is great because downtown is only 3 blocks away and you are 6 blocks from the beach. The cabins have a pool within the community for renters to dive in and there is a fully stocked fire pit in the back yard.

Accommodation capacity : 14
Cost: $ 378 / night
In line: airbnb.com

photo: Airbnb

Comfortable with your family in this 2 bedroom cottage located in a quiet cul-de-sac next to a charming pond. Gaze at the stars by the pond with a lit fire or head to the clubhouse to play ping pong, foosball and the heated swimming pool.

Sleeps: 6
Cost: $ 255 / night
In line: airbnb.com

photo: Airbnb

If golf is your sport, this rental will give you the feeling of hitting a hole in one, as it is located close to three championship golf courses. You also have access to three swimming pools, tennis courts, two playgrounds, on-site restaurants, and miles of scenic hikes. You are also just minutes from Lake Geneva, Delavan, Williams Bay and Fontana.

Accommodation capacity : 6
Cost: $ 343 / night
In line: airbnb.com

photo: Airbnb

Kids will literally panic when they see the massive 1,600 square foot indoor pool room with a hot tub. Add to that the seclusion of the woods, the cul-de-sac location and a large yard with a fireplace and a covered gazebo and you have everything you need for a relaxing vacation.

Accommodation capacity : 8
Cost: $ 450 / night
In line: airbnb.com

photo: Airbnb

Walk out right outside your back door and fish all day, relax on the sandy beach of the fishing pond or get on a paddleboard. If you prefer the pool to the pond, there is also an inground pool and hot tub. End the night with the family by relaxing in the games room.

Accommodation capacity : 16
Cost: $ 550 / night
In line: airbnb.com

photo: Airbnb

Plan a stay in River North at this 2 bedroom condo with breathtaking views and amenities. The pool has a hot tub, cabanas, lounge chairs, and access to grilling stations and fire pits. Bond with the family on the pétanque court or show the kids your skills in the arcade room which features pinball machines and skeeball.

Accommodation capacity : 4
Cost: $ 250 / night
In line: airbnb.com

photo: Airbnb

Please note: you will never want to leave this modern and luxurious getaway again. Swan takes a dip in the backyard pool, relax on the rooftop balcony equipped with heat lamps, and use the chef’s kitchen to whip up a home-cooked meal. Retreat to the movie theater for a memorable family movie night!

Accommodation capacity : 8
Cost: $ 570 / night
In line: airbnb.com

photo: Airbnb

This one is a bit of a splurge, but with 7 bedrooms, there is enough space to bring multiple families! This modern farmhouse sits on an acre of land and the pool is 3 ‘to 12’ deep and includes a slide and diving board. Also. . . there are chickens, which will absolutely delight children who like life on the farm a little.

Accommodation capacity : 16
Cost: $ 1,999 / night
In line: airbnb.com

photo: Airbnb

This 4 bedroom ranch in Glen Oak Acres places you minutes away from Wagner Farm, bike paths, walking trails and downtown Northfield, Glenview and The Glen. The outdoor living space includes a heated inground pool, barbecue, pergola and fireplace.

Accommodation capacity : 7
Cost: $ 371 / night
In line: airbnb.com

—Maria Chambers

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