Villa vacation rentals in Simcoe County

4.87 out of 5 average rating, 15 reviews

A modern two-story home features a blend of stone and stucco exterior. A covered front porch with elegant columns invites entry. Large windows allow natural light to illuminate the facade, and a driveway leads to a stylish garage door, surrounded by a landscaped front yard.

Villa in Newmarket

Fairy Lake Manor

Welcome to our luxurious home in the heart of downtown Newmarket! This spacious and stylish retreat offers the perfect blend of modern amenities and upscale comfort, making it the ideal spot for your next getaway. Features open-concept living area, multiple bedrooms with plenty of natural light, chic decor. The fully-equipped gourmet kitchen perfect for preparing meals during your stay. Relax in the outdoor living area, hike at fairy lake park or take a dip at the Gorman community outdoor pool .

An outdoor seating area is displayed with a glass-top coffee table surrounded by two chairs and a spacious sectional sofa. Lush greenery and trees are visible in the background, creating a serene view of the natural landscape.

4.83 out of 5 average rating, 6 reviews

Villa On The Green

Welcome to this spacious 3-bed, 2-bath villa located within the prestigious Muskoka Bay Resort. Nestled in a luxe enclave of select villas overlooking the pristine greens, this 5 * property offers an unparalleled experience for avid golfers and relaxation seekers alike. Enjoy access to top-tier amenities, including a stunning cliffside restaurant where you can indulge in exquisite int'l cuisine. Whether you're teeing off on the world-class golf course or unwinding, this is the perfect retreat.

4.82 out of 5 average rating, 17 reviews

A modern living room features a light-colored sectional sofa and a black armchair, creating a comfortable seating area. A sleek fireplace is centered on the wall, with a decorative mantle and artwork above. Large windows provide natural light, enhancing the welcoming atmosphere.

Villa in Aurora

6BR 6BA Luxe Aurora Retreat | Pool Table, Sun Room

**Sleeps 8 upstairs, 8 downstairs. Please let us know if you are more than 16 guests.** NEWLY RENOVATED! BBQ now available! Discover the perfect oasis at our spacious 6-bedroom haven in the scenic neighborhood of Aurora. Steps from a beautiful pond, this retreat is great for family, friends or colleagues. Unwind in the sunroom, challenge your group to a fun game of billards or ping pong. Your retreat, your way – welcome to your dream getaway. 10min from Madison Greenhouse & many Golf Clubs

The great room features a large leather sectional sofa arranged around a wooden coffee table. Natural light fills the space through multiple windows, and a stylish area rug complements the modern design. The open concept leads to a kitchen area visible in the background.

Villa in Bradford West Gwillimbury

4.71 out of 5 average rating, 124 reviews

Executive Villa - Year Round Swim Spa & Game Room

Mediterranean inspired country villa: Get away from the big city and unwind in this luxurious custom built bungaloft - total 6000 Sq Ft livable space . Situated in an exclusive estate community enclave and sits on a private 2 acre property. The residence boasts a high-end kitchens, year round swim spa (outside) and game room (basement). Enjoy great shopping at nearby Tanger Outlet Mall. A short drive to Cooks Bay Marina, & only 20 minutes from Canada’s Wonderland & Snow Valley Ski resort.

A circular arrangement of four dark blue Adirondack chairs features cozy white blankets draped over the arms. In the center, a fire pit sits on a stone patio, surrounded by a lush green lawn and trees displaying vibrant autumn foliage.

4.89 out of 5 average rating, 19 reviews

Luxury Modern Muskoka Retreat

Exquisite Scandinavian-style private villa surrounded by a lush forest landscape. Situated on the grounds of the Muskoka Bay Golf Resort, this 5 star property won’t disappoint. RARE special corner villa with walls of windows. Only two in the entire community. Enjoy the infinity pool (May-Oct), tennis, trails, golfing or just a lovely bonfire overlooking the hilly landscape. Don’t forget to visit the clubhouse and all its amenities including state of the art gym & 5 star dining experience!

A modern living area features a spacious gray sofa with decorative pillows, an upholstered chair, and a large ottoman placed on a soft area rug. Bright natural light fills the room through expansive sliding glass doors that open to a serene outdoor view.

4.93 out of 5 average rating, 15 reviews

Nordic Elegance Villa in Muskoka

Welcome to Nordic Elegance Villa at Muskoka Bay Resort! This villa showcases Scandinavian design and offers a sophisticated ambiance. As a 5-star property, it is designed to exceed your expectations, with amenities tailored for families. Explore a wide array of Muskoka Bay Resort's amenities, including a swimming pool, sauna, trails, and golfing (ranked #1 golf course in Ontario). Minutes away from local parks and Muskoka Steamships/Discovery Centre. Bring the family and enjoy all the fun!

4.78 out of 5 average rating, 131 reviews

A modern living area features a leather sectional sofa placed around a circular coffee table. A mounted television is displayed over a stone fireplace. Natural light is filtered through large windows, enhancing the open feel of the space, which includes a stylish accent chair.

Villa in Collingwood

The Family Escape Townhome

Conveniently located in Collingwood, Ontario only 1.5 hours from the GTA, this home is a 5 minute drive to Blue Mountain Resort, a 7 minute drive to Northwinds Beach & 20 minute drive to Wasaga Beach (the largest fresh water beach in the world!). Enjoy hiking/biking trails, golf and so much more! Set your day’s agenda from hitting the slopes, to relaxing at the spa. This home will make you feel warm and welcomed to the four-season destination of Collingwood & our neighbour Blue Mountain!

4.86 out of 5 average rating, 7 reviews

Villa in Tiny

The Sandals Beach Villa & Spa

Escape to this serene, newly refreshed 5-bedroom all-seasons cottage nestled in Tiny Township on the beautiful shores of Georgian Bay. Whether you're seeking a peaceful retreat or an adventure-filled getaway, this cottage offers the perfect blend of relaxation and excitement. In the summer, soak up the sun on pristine beaches, and in winter, hit the nearby ski slopes for some snowy fun. Ideal for families and friends, this is your year-round sanctuary away from the hustle of city life.

An aerial view captures the resort’s clubhouse surrounded by vibrant autumn foliage and rolling landscapes. Two outdoor pools are visible, complemented by sun loungers and a rocky terrain. The expansive greenery suggests recreational opportunities nearby, inviting exploration of the diverse natural surroundings.

4.88 out of 5 average rating, 25 reviews

ScandinaVilla Retreat

ScandinaVilla, an Exquisite Scandinavian-Style Private Villa is surrounded by a lush forest landscape and nestled on the grounds of the sought after Muskoka Bay Golf Resort community. Enjoy golfing, hiking trails, cycling, and water activities in nearby nature & beaches in the summer; and snowshoeing, cross country skiing, ice fishing and ice skating in the winter months. Visit the clubhouse and benefit from all its amenities including state of the art gym & 5-star dining experience!

Villa in Whitchurch-Stouffville

A serene pool area is illuminated by soft lighting, highlighting the clear water and inviting atmosphere. Surrounding the pool, comfortable lounge chairs and seating areas are arranged for relaxation. The natural surroundings create a peaceful backdrop, enhanced by the warm glow of lights.

4.97 out of 5 average rating, 35 reviews

Cedar Escape • Sauna • 10-Acre Private Forest

Welcome and discover Your Forest Sanctuary. Nestled in a lush 10-acre private forest, find a haven where nature embraces you. Unwind along trails, feel the refreshing forest shower, and gather around the fire pit for magical moments. Indulge in sauna bliss and poolside serenity, immersed in nature's tranquility. Close to the city, yet far from hustle and bustle. Come, relax, and discover the magic of living in harmony with nature. Also enjoy the convenience by hi-speed internet.

4.97 out of 5 average rating, 71 reviews

An outdoor dining area is set with a dark table surrounded by comfortable chairs. Elegant tableware and floral arrangements decorate the table, while soft lighting creates a warm ambiance against a backdrop of lush greenery.

Villa in Kettleby

Entire Villa with beautiful fenced backyard

This cozy and elegant villa is situated on 0.5 acre with spacious first-floor master bedroom suite, lovely sunroom, beautiful fenced backyard, fire pit and long driveway. Awesome location with lots of greenery, fall colours and fairy tale snow scenes! Everything is close by but you are in the peaceful countryside. 3 mins from HWY 400 and 30 mins from airport. No any kind of party is allowed here and no any street parking. Thanks for your great understanding!