
Holiday rentals with a pool in Simcoe County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Simcoe County
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Simcoe County rentals with a pool
House rentals with a pool

Country Family Getaway with Pool and Trails

Cute and Cozy House

Spacious Chalet close to Ski resort. Pet friendly!

King Bed, Pool, Ravine View, Near Ski Hills

Spacious 4BR Snowbridge Home with Shuttle Access

Serene mountainside home View/Shuttle Bus/Pool

Custom home that feels like the Spa

10 Acre Farmhouse with Pool + 5 Bedrooms/3 Baths
Apartment rentals with a pool

Large, luxury, upper floor condo, steps to Village

The Fairway Chalet

Stylish & Spacious 2 Bdrm/2 bths/2 balc Condo Loft

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

Beautiful Condo, 2 Bedrooms and a Den in a Resort!

2 Bedroom, 2 Level Condo on Blue Mountain!

Exceptional 2+1 ground floor condo @Friday Harbour

Friday Harbour Luxury Condo, Sleeps 4
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- Blue Mountain Village
- Horseshoe Resort
- Mount St. Louis Moonstone
- Snow Valley Ski Resort
- Port Carling Golf & Country Club
- Lakeridge Ski Resort
- Beaver Valley Ski Club
- Hockley Valley Resort - Golf, Spa and Ski
- Georgian Bay Islands National Park
- Muskoka Lakes Golf and Country Club
- South Muskoka Curling and Golf Club
- Osler Bluff Ski Club
- Devil's Glen Country Club
- Caledon Country Club
- Jungle Land
- LEGOLAND Discovery Centre Toronto
- Uplands Golf & Ski Club
- The Thornhill Club
- Ladies' Golf Club of Toronto
- The National Golf Club of Canada
- The Pulpit Club
- The Club At Bond Head
- Eagles Nest Golf Club
- Barrie Country Club
- Things to do Simcoe County
- Things to do Ontario
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- Food and drink Ontario
- Things to do Canada
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