Vacation 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.
Vacation 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
Home in The Blue Mountains
4.91 out of 5 average rating, 173 reviewsPool Open/Sauna/Shuttle Bus/Pool table/2 King bed
Home in The Blue Mountains
4.95 out of 5 average rating, 151 reviewsSerene mountainside home View/Shuttle Bus/Pool
Home in Shanty Bay
5 out of 5 average rating, 40 reviewsBeautiful Town For 5, Ravine View, Resort Pool
Home in Elmvale
4.9 out of 5 average rating, 10 reviewsCozy Lakefront Cottage with Hot tub and Pool.
Home in Midland
4.76 out of 5 average rating, 33 reviewsOur vacation home. Fully equipped. Pool. Fire Pit.
Home in Collingwood
4.84 out of 5 average rating, 37 reviewsBatteaux Chalet - Pool + Blue Mountain Skiing
Home in Newmarket
5 out of 5 average rating, 12 reviewsBeautiful Pond View stay!
Home in Honeywood
4.98 out of 5 average rating, 51 reviewsSunnylea Acres
Condo rentals with a pool
Condo in The Blue Mountains
4.97 out of 5 average rating, 118 reviewsRustic Chic Renovated 2Bd Condo by Village
Condo in The Blue Mountains
4.93 out of 5 average rating, 165 reviewsLe Petite Chalet - Shuttle to Blue / Outdoor Pool
Condo in The Blue Mountains
4.88 out of 5 average rating, 362 reviewsBase of Blue Mountain, Modern Updated Studio
Condo in The Blue Mountains
4.95 out of 5 average rating, 213 reviewsCozy & Charming Retreat at Blue Mountain
Condo in The Blue Mountains
4.89 out of 5 average rating, 194 reviewsHidden Haven - Shuttle to Blue / Outdoor Pool
Condo in The Blue Mountains
4.92 out of 5 average rating, 251 reviewsCozy Studio Mountainside stay in Blue Mountains
Condo in The Blue Mountains
4.9 out of 5 average rating, 381 reviewsSpring Getaway | Blue Mountain
Condo in Oro
4.89 out of 5 average rating, 133 reviews4-Bed Country Club Haven with Pool, BBQs, and More
Destinations to explore
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