Cook County rentals with pool

We found 849 rentals with pool — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

September 2025

October 2025

Explore Cook County rentals with pools

"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg "

Sleeps 4 · 25 bedrooms · 1 bathroom

Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking

Sleeps 5 · 2 bedrooms · 2 bathrooms

Premier Host

Luxury 5BR Family Getaway – Heated Pool, Hot Tub, Fire pit, Game Room,

Sleeps 12 · 5 bedrooms · 4 bathrooms

Premier Host

Pet/Family Friendly Farmhouse: Sleeps 10, Firepit, 1 Hour from CHI

Sleeps 10 · 4 bedrooms · 2+ bathrooms

Full experience: bathtub, patio with grill/firepit, smart TVs, ping pong.

Premier Host

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

Sleeps 10 · 4 bedrooms · 2+ bathrooms

Find spaces that suit your style

Rentals with Pool in Cook County

Rentals with Pool in Hickory Hills

Rentals with Pool in Park Ridge

Rentals with Pool in Wilmette

Rentals with Pool in Des Plaines

Rentals with Pool in Evanston

Rentals with Pool in Orland Park

Rentals with Pool in Skokie

Rentals with Pool in Elk Grove Village

Rentals with Pool in Robbins

Rentals with Pool in Oak Park

Rentals with Pool in Tinley Park

Rentals with Pool in Chicago

Rentals with Pool in Forest Park

Rentals with Pool in Oak Lawn

Rentals with Pool in Arlington Heights

Rentals with Pool in Palatine

Rentals with Pool in Schaumburg

Rentals with Pool in Mount Prospect

Rentals with Pool in Glenview

Holiday Rental options in Cook County

Ski holiday rentals in Cook County

Lake holiday rentals in Cook County

Beach holiday rentals in Cook County

Pet-friendly holiday rentals in Cook County

Monthly rentals in Cook County

Mountain holiday rentals in Cook County

Family-friendly holiday rentals in Cook County

Oceanfront holiday rentals in Cook County

Holiday rentals with spa pool in Cook County

It's easy to contact hosts and keep track of all your messages when you have a Bookabach account

Explore Cook County rentals with pools

"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg "

Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking

Luxury 5BR Family Getaway – Heated Pool, Hot Tub, Fire pit, Game Room,

Pet/Family Friendly Farmhouse: Sleeps 10, Firepit, 1 Hour from CHI

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

Casa 22 • Luxury Modern House for 6 • 3 Bed, 2 Bath

Find spaces that suit your style

Rentals with Pool in Cook County

Holiday Rental options in Cook County