Cook County rentals with pool

We found 841 rentals with pool — enter your dates for availability

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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

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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