8 Airbnb Rentals for Chicago Families with Epic Pools

Book a splash-worthy vacation without getting on a plane or leaving our time zone.

By Maria Chambers July 11, 2022

Airbnb

No need to book family vacations to far-away destinations this summer, because this is the time of year we live for as Chicagoans. The temps are perfection, the activities are aplenty and the landscape is gorgeous. If you’d like an escape from your own four walls, turn to Airbnb. From high-rises in Chicago to mini road trips to farmhouses with chickens, you can snag an Airbnb rental that features a pool and fun family-focused amenities.

137-Year-Old Farmhouse | Lake Forest

This updated 5-bedroom farm home in Lake Forest is a great option for extended families looking to spend quality time together. It's a stone's throw from a public golf course, downtown Lake Forest is just a mile down the road and a romp in the sand at the beach is just two miles away.

Sleeps: 9
Cost: $700/night
Online: airbnb.com

Farmesque with a Splash of Modern | New Buffalo

This 5-bedroom stunner built in 2019 will have you feeling like you rolled back time with trough sinks, a claw foot tub, distressed floors and cedar beams, but has modern touches and amenities throughout. Galien River Marsh is across the street and there are several bikes on property to take a cruise. This is great because the downtown area is just 3 blocks away and you're 6 blocks from the beach. The cottages have a pool within the community for renters to take a plunge and there's a fully-stocked firepit in the backyard.

Sleeps: 14
Cost: $632/night
Online: airbnb.com

1 Pond Place | Union Pier

Cozy in with the family in this 2-bedroom cottage located on a quiet cul-de-sac next to a charming pond. Stargaze pond-side with fire blazing or head to the clubhouse for ping pong, foosball and a heated pool.

Sleeps: 6
Cost: $335/night
Online: airbnb.com

A Fisherman's Dream Retreat | Milwaukee

Step right outside your back door and fish the day away, chill on the sand beach at the fishing pond or hop on a paddleboard. If you prefer pool to pond, there's also an in-ground pool and hot tub. End the night as a family relaxing in the game room.

Sleeps: 16
Cost: $550/night
Online: airbnb.com

Pool with a View | River North

Plan a staycation in River North at this 2 bedroom condo with breathtaking views and amenities. The pool features a hot tub, cabanas, chaise lounges and access to grill stations and fire pits. Bond with the family on the bocce court or show the kids your skills in the arcade that includes pinball machines and skeeball.

Sleeps: 4
Cost: $814/night
Online: airbnb.com

Modern Spanish Abode | Plainfield

Warning: You'll never want to leave this modern, luxurious escape. Swan dive into the backyard pool, chill on the rooftop balcony equipped with heat lamps and take advantage of the chef's kitchen to whip up a home-cooked meal. Retire to the theater room for a memorable family movie night!

Sleeps: 8
Cost: $570/night
Online: airbnb.com

Stately Manor | Wayne

This one is a bit of a splurge, but with 7 bedrooms, there's enough space to bring along multiple families! This modern farmhouse sits on an acre of land and the pool ranges in depth from 3' to 12' and includes a slide and diving board. Also. . . there are chickens, which will absolutely delight the kids who like a bit of the farm life.

Sleeps: 16
Cost: $1,999/night
Online: airbnb.com

Sweet Ranch | Glenview

This 4-bedroom ranch in Glen Oak Acres puts you within minutes of Wagner Farm, bike trails, walking paths and downtown Northfield, Glenview and The Glen. The outdoor living space includes an in-ground heated pool, grill, pergola and firepit.

Sleeps: 7
Cost: $371/night
Online: airbnb.com