
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

Cute and Cozy House

The Cozy Corner Townhome - Shuttle to the Village

Large 4 Br - 4.5 Bathroom: 2 King beds/Sauna/games

King Bed, Pool, Gym, Ravine View, Your Getaway!

Our vacation home. Fully equipped. Pool. Fire Pit.

Blue Mountain Retreat In Historic Snowbridge

Serene mountainside home with View/Shuttle Bus

Beautiful Cottage w Indoor Pool, Sauna, Pool Table
Condo rentals with a pool

Blue Mountain Getaway at North Creek Resort

Mountainside Escape at Blue - Outdoor Pool

Blue Mountain Condo. The perfect staycation!

Cozy Studio Mountainside stay in Blue Mountains

Hidden Haven - Shuttle to Blue / Private Patio

Highlands Lodge & Loft - Shuttle to the Village

Ski in/out @ North Creek W King bed! New Hot Tub

Marina view at Friday Harbour 2bd/2bth Pool option
Other vacation rentals with a pool

Lake/Marina Front, Luxury 2 Storie 1500 Sqft At FH

Après Blue- 2bed2bath w/Pool 6 min walk to village

Luxurious Friday Harbour Condo

Perfect ~Huge Patio ~ 2BR ~ BBQ ~ Friday Harbour

Walkout to Courtyard w/ Pool, Hot Tub and Fire Pit

Trendy 1 Bdrm w/Pool & Hot Tub View

Wildwood HotTub+Indoor/Outdoor Pool+Sauna+GameRoom

Perfect 2 bedrm resort style unit Getaway-Top Host
Destinations to explore
- Rentals with beach access Simcoe County
- Bed and breakfasts Simcoe County
- Cottage rentals Simcoe County
- Cabin rentals Simcoe County
- Rentals with breakfast Simcoe County
- Guesthouse rentals Simcoe County
- Villa rentals Simcoe County
- Hotel rentals Simcoe County
- Family-friendly rentals Simcoe County
- Bungalow rentals Simcoe County
- Vacation home rentals Simcoe County
- Chalet rentals Simcoe County
- Waterfront rentals Simcoe County
- Farmstay rentals Simcoe County
- RV rentals Simcoe County
- Tiny house rentals Simcoe County
- Rentals with outdoor seating Simcoe County
- Pet-friendly rentals Simcoe County
- Rentals with a washer and dryer Simcoe County
- Rentals with a fireplace Simcoe County
- Dome rentals Simcoe County
- Rentals with a fire pit Simcoe County
- Private suite rentals Simcoe County
- Rentals with a sauna Simcoe County
- Rentals with a patio Simcoe County
- Fitness-friendly rentals Simcoe County
- Rentals with a kayak Simcoe County
- House rentals Simcoe County
- Rentals with a hot tub Simcoe County
- Condo rentals Simcoe County
- Rentals with lake access Simcoe County
- Ski-in/ski-out rentals Simcoe County
- Boutique hotel rentals Simcoe County
- Townhouse rentals Simcoe County
- Apartment rentals Simcoe County
- Smoking-friendly rentals Simcoe County
- Beachfront rentals Simcoe County
- Loft rentals Simcoe County
- Rentals with an EV charger Simcoe County
- Rentals with pools Ontario
- Rentals with pools Canada
- Blue Mountain Village
- Horseshoe Resort
- Snow Valley Ski Resort
- Beaver Valley Ski Club
- Osler Bluff Ski Club
- Craigleith Ski Club
- Devil's Glen Country Club
- Hockley Valley Resort - Golf, Spa and Ski
- Angus Glen Golf Club
- Port Carling Golf & Country Club
- The Georgian Peaks Club
- Lakeridge Ski Resort
- TPC Toronto at Osprey Valley
- Lake Joseph Golf Club
- Mount St. Louis Moonstone
- The Club At Bond Head
- Wooden Sticks Golf Club
- Muskoka Lakes Golf and Country Club
- Georgian Bay Islands National Park
- Caledon Country Club
- Muskoka Bay Resort
- Windermere Golf & Country Club
- Dagmar Ski Resort
- Barrie Country Club