Dufferin County rentals with pool

We found 49 rentals with pool — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

October 2025

November 2025

Explore Dufferin County rentals with pools

Peaceful evening swims

Premier Host

“The Hockley Hideaway”, sharing our unique property for your unique experiences❤️

Sleeps 10 · 5 bedrooms · 2 bathrooms

Exterior

Historic Farmhouse with Pool, Hot Tub, Outdoor Shower, Stream,Barn, on 100 Acres

Sleeps 16 · 8 bedrooms · 2+ bathrooms

Miscellaneous

Heaven on 5th, Luxury in the Canadian Countryside, 9 bedrooms, hot tub, and pool

Sleeps 24 · 9 bedrooms · 3+ bathrooms

Find spaces that suit your style

House

Condo/Apartment

Rentals with Pool in Dufferin County

Rentals with Pool in Amaranth

Rentals with Pool in Melancthon

Rentals with Pool in Shelburne

Rentals with Pool in Mulmur

Rentals with Pool in Orangeville

Rentals with Pool in East Garafraxa

Rentals with Pool in Grand Valley

Rentals with Pool in Mono

Holiday Rental options in Dufferin County

Holiday rentals with spa pool in Dufferin County

Family-friendly holiday rentals in Dufferin County

Mountain holiday rentals in Dufferin County

Monthly rentals in Dufferin County

Oceanfront holiday rentals in Dufferin County

Lake holiday rentals in Dufferin County

Pet-friendly holiday rentals in Dufferin County

Beach holiday rentals in Dufferin County

Ski holiday rentals in Dufferin County

a4b5b619-400d-a5af-5d5d-b43752bd254aa0a5e6cd-4b10-4347-a7c9-0f9824e75457