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Simcoe County Villas

Escape to paradise in Simcoe County! Discover luxurious villas with private pools, hot tubs, and stunning views. From relaxation to adventure, our expert guide reveals the best villas, activities, and experiences in Midland and Wasaga Beach. Read now and plan your dream getaway!

Villas in Simcoe County

Mountain House Escape
£136  night
6
4
2
Details View Offers
Luxury Europian Waterfront Villa in Lake Simco, considered Venice of the North
£424  night
8
5
6
Details View Offers
Relaxing Chalet Retreat at Sharon, ON
5.0/5
£297  night
8
4
2
Details View Offers
Luxury Lake Simcoe Waterfront Estate
£1215  night
14
5
5
Details View Offers
Luxurious 11-Bedroom Villa with Indoor Pool, Outdoor Sauna & Jacuzzi
5.0/5
£810  night
24
11
7
Details View Offers
Newly renovated luxury 3500 SF Home surrended by trees on a 5 acres land
4.9/5
£212  night
11
6
3
Details View Offers
Charming Cottage on Lake Simcoe
5.0/5
£335  night
6
3
2
Details View Offers
Villa in Aurora Near Couple Golf Course
£299  night
8
5
6
Details View Offers
Grand 10BR 9BA Waterfront Retreat Near Muskoka | Sleeps 30 | Perfect for Events
£898  night
30
10
9
Details View Offers
Breathtaking Rosemont Villa Near Earl Rowe Provincial Park
4.0/5
£157  night
12
3
4
Details View Offers
Luxury Estate Home getaway in Caledon, Pet Friendly
3.5/5
£125  night
10
5
4
Details View Offers
Real home feeling stay!
5.0/5
£295  night
8
3
4
Details View Offers
Tranquil Waterfront Villa
5.0/5
£299  night
10
4
4
Details View Offers
Black Water Golf Villa, Jackson's Point Harbour is 10 min drive
5.0/5
£543  night
16
5
3
Details View Offers
*NEW* Naturskön Cottage | Mountain Views | Hot Tub | Volleyball | 5 Acres
5.0/5
£477  night
12
3
2
Details View Offers
The Family Escape-5 min to the slopes & the shore!
4.5/5
£73  night
7
3
3
Details View Offers
Elegant & Cozy English Villa with beautiful fenced backyard
5.0/5
£258  night
9
3
3
Details View Offers
Sandals Of Tiny ~ Sleep16✔Hot tub✔Sauna✔3 Min Walk to Private Beach Georgian Bay
5.0/5
£1358  night
16
6
3
Details View Offers
Lakeview resort style suite (Twin or King)
5.0/5
£71  night
3
1
1
Details View Offers
Luxurious 5 BRLuxurious 5 BR/3.5 BA Waterfront Over 5000 SqFt/3.5 BA Waterfront Over 5000 SqFt
£602  night
10
5
4
Details View Offers

Why a holiday villa in Simcoe County

Located just north of Toronto, Simcoe County offers a tranquil escape from city life without sacrificing convenience. Our luxurious villas are nestled among picturesque towns and rolling countryside, providing the perfect setting for relaxation and rejuvenation.

Whether you're looking to unwind in a private hot tub under the stars or enjoy a family vacation with plenty of room to roam, our Simcoe County villas have something for everyone. With their spacious living areas, fully equipped kitchens, and stunning views of the surrounding landscape, these holiday homes are the perfect base for exploring all that this beautiful region has to offer.

When to rent a villa in Simcoe County

When it comes to planning your Simcoe County villa holiday, timing is everything. The region's four distinct seasons offer unique experiences, but the peak tourist season runs from June to September, with July and August being the warmest months. This is ideal for outdoor enthusiasts who want to enjoy swimming, kayaking, or hiking in the picturesque countryside. If you're looking for a more relaxed pace, consider visiting in the spring (May-June) or fall (September-October), when the temperatures are mild and the crowds are smaller.

Winter brings its own charm to Simcoe County, with snow-covered landscapes, frozen lakes, and cozy villas perfect for snuggling up by the fireplace. If you're a fan of winter sports like skiing, ice fishing, or snowshoeing, December to March is your best bet. And if you're looking for a romantic getaway or a family vacation during the holiday season, our Simcoe County villas are decked out in festive cheer from late November to early January. Whatever your style, there's always a perfect time to visit and make unforgettable memories in this beautiful Ontario region.

Where to go in Simcoe County

For a villa holiday in Simcoe County, consider setting your sights on the charming town of Midland. Located at the southern tip of Georgian Bay, Midland offers a unique blend of small-town charm and big-city amenities. Stroll along the waterfront, visit the iconic Huronia Museum, or take a romantic dinner cruise around the bay. And when you're ready to unwind, retreat to your villa's private hot tub or pool for a relaxing soak under the stars.

Alternatively, head to the scenic town of Wasaga Beach, where the longest freshwater beach in the world beckons with its sugar-white sand and gentle waves. After a day of soaking up the sun, indulge in fresh seafood at one of the many local eateries or take a sunset stroll along the shoreline. Whether you're looking for adventure or relaxation, our villas in Simcoe County's Midland and Wasaga Beach areas offer the perfect blend of tranquility and excitement.

Picture of two young girls swimming in a pool with their floatation rings
Family friendly villas
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Picture of a Titleist golf ball on the edge of the hole on a golfing green
Villas near golf course
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Villas in Simcoe County

Mountain House Escape
£136  night
6
4
2
Details View Offers
Luxury Europian Waterfront Villa in Lake Simco, considered Venice of the North
£424  night
8
5
6
Details View Offers
Relaxing Chalet Retreat at Sharon, ON
5.0/5
£297  night
8
4
2
Details View Offers
Luxury Lake Simcoe Waterfront Estate
£1215  night
14
5
5
Details View Offers
Luxurious 11-Bedroom Villa with Indoor Pool, Outdoor Sauna & Jacuzzi
5.0/5
£810  night
24
11
7
Details View Offers
Newly renovated luxury 3500 SF Home surrended by trees on a 5 acres land
4.9/5
£212  night
11
6
3
Details View Offers
Charming Cottage on Lake Simcoe
5.0/5
£335  night
6
3
2
Details View Offers
Villa in Aurora Near Couple Golf Course
£299  night
8
5
6
Details View Offers
Grand 10BR 9BA Waterfront Retreat Near Muskoka | Sleeps 30 | Perfect for Events
£898  night
30
10
9
Details View Offers
Breathtaking Rosemont Villa Near Earl Rowe Provincial Park
4.0/5
£157  night
12
3
4
Details View Offers
Luxury Estate Home getaway in Caledon, Pet Friendly
3.5/5
£125  night
10
5
4
Details View Offers
Real home feeling stay!
5.0/5
£295  night
8
3
4
Details View Offers
Tranquil Waterfront Villa
5.0/5
£299  night
10
4
4
Details View Offers
Black Water Golf Villa, Jackson's Point Harbour is 10 min drive
5.0/5
£543  night
16
5
3
Details View Offers
*NEW* Naturskön Cottage | Mountain Views | Hot Tub | Volleyball | 5 Acres
5.0/5
£477  night
12
3
2
Details View Offers
The Family Escape-5 min to the slopes & the shore!
4.5/5
£73  night
7
3
3
Details View Offers
Elegant & Cozy English Villa with beautiful fenced backyard
5.0/5
£258  night
9
3
3
Details View Offers
Sandals Of Tiny ~ Sleep16✔Hot tub✔Sauna✔3 Min Walk to Private Beach Georgian Bay
5.0/5
£1358  night
16
6
3
Details View Offers
Lakeview resort style suite (Twin or King)
5.0/5
£71  night
3
1
1
Details View Offers
Luxurious 5 BRLuxurious 5 BR/3.5 BA Waterfront Over 5000 SqFt/3.5 BA Waterfront Over 5000 SqFt
£602  night
10
5
4
Details View Offers