Villa holiday rentals in Simcoe County

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Top-rated villa rentals in Simcoe County

Guests agree: These villas are highly rated for location, cleanliness and more.

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Top Guest favourite

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.

Villa in Whitchurch-Stouffville

4.98 out of 5 average rating, 46 reviews

Cedar Escape • Sauna • 10-Acre Private Forest

License: PRSTR2026-0229 Welcome to your private 10-acre forest estate, an exclusive sanctuary where refined luxury meets pristine nature. Wander serene woodland trails, refresh beneath the open-air forest shower, and gather fireside under a canopy of stars. Indulge in the soothing sauna, unwind poolside in complete privacy, and embrace the rare stillness surrounding you. Just minutes from the city, yet utterly secluded—offering elevated comfort, tranquility, and seamless high-speed connectivity.

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Villa in Creemore

4.96 out of 5 average rating, 27 reviews

Creemore Mulmur Estate Heated Pool/Tennis

Spacious Country Estate overlooking the Niagara Escarpment in Mulmur near,Avening, Creemore, Mansfield Favourite location of groups, weddings,acres of spacious landscape, pool, tennis, hot tub, fire pit. Mosquito free spray is used seasonally on property Weddings/Reunions welcome - party fee based on event size. Pets in LOFT ONLY Massive Great Room PoolTable/Dining/Kitchen/Balcony/BBQ/PowderRoom Lower Level 3 bedrooms/2 full bath /Lounge/Gym/walk out to patio/hot tub. Loft- King bed/futon

LocationFamilyComfort

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

4.68 out of 5 average rating, 137 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.

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Top Guest favourite

A multi-purpose room is characterized by large windows that allow natural light to fill the space. Various seating options, including soft chairs and cushions, are arranged around a central area with a decorative rug. Plants add a touch of nature to the serene environment.

Villa in Georgina

4.94 out of 5 average rating, 35 reviews

Charming Mid-Century Villa on 10 Acres Forest Land

We call it House of Wonders! book with us to relax and unwind in peace & tranquillity. Enjoy full privacy on 10 acres w/scenic forest trails, garden, patio with gazebo lit at night, 4 different outdoor fire pits, various outdoor sitting and dinning areas. Read your favourite book on the hammock, get busy with bird watching or take advantage of the equipped indoor gym. This 2 storey villa with brick interiors has lots of characters with a fully equipped kitchen, freestanding bathtub & more

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Guest favourite

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.

Villa in Gravenhurst

4.88 out of 5 average rating, 33 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!

LocationFamilyHospitality

Villa in Collingwood

4.76 out of 5 average rating, 160 reviews

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!

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Guest favourite

Villa in Tiny

4.98 out of 5 average rating, 120 reviews

In Pines •Family-Friendly • Screened Porch • Beach

Escape to In Pines — a bright and spacious retreat nestled in Tiny, LaFontaine, just a 3–4 minute walk to the beautiful sandy beaches of Georgian Bay. Wake up to sunlight streaming through large windows, enjoy peaceful mornings surrounded by nature, and unwind by the fire pit or on the cozy screened porch after a day at the beach. Designed for comfort and connection, this home is perfect for families and groups looking to relax, recharge, and create lasting memories in every season.

LocationFamilyNearby

A rustic villa is set beneath a canopy of green trees, featuring brick walls and a spacious yard. A playset with a slide and swings occupies the foreground, while the structure's multiple windows offer views of the surrounding forest.

Villa in Whitchurch-Stouffville

4.54 out of 5 average rating, 37 reviews

Luxury countryside/Forest Villa (close to lake)

Enjoy your peaceful country life but close to city. Close to highway 404 and Walmart. Walk to forest and hiking trail. A cottage style villa on a 2 Acres land. Each room has fantastic window view. Spacious main floor with cozy 4 bedrooms on second floor. Spacious basement has home theater, office and bedroom. This stylish place to stay is perfect for family or group trips. Only 15 mins drive to public lake with beach. Short term license number is PRTRS20250769.

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Guest favourite

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

4.98 out of 5 average rating, 90 reviews

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!

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Guest favourite

A contemporary two-story villa is shown with distinct gable roofing. The facade features a combination of dark and natural wood panels. Large windows allow natural light to illuminate the interiors. The villa is surrounded by well-maintained greenery and an open parking area is visible in front.

Villa in Gravenhurst

4.96 out of 5 average rating, 48 reviews

Luxury Resort Villa in Muskoka

Escape to our brand-new 3-bedroom villa at Muskoka Bay Resort! This serene, two-level end-unit comfortably accommodates families and groups, featuring modern comforts, a fully equipped kitchen, and stunning golf course views. Resort amenities, including the pool, sauna, lake access, fitness center, restaurant, EV charging station, and parking, are available for an additional daily fee. A perfect year-round retreat near Lake Muskoka and Gravenhurst Wharf.

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Guest favourite

A spacious living room features contemporary furnishings, including two sleek sofas arranged around a central coffee table. Tall ceilings and soft lighting highlight a large artistic photograph of trees. Neutral colors enhance the room's airy ambience, complemented by warm wood flooring.

Villa in Collingwood

5.0 out of 5 average rating, 16 reviews

Luxury Collingwood Getaway

Exquisite Custom Built Bungalow with luxurious finishes throughout. Main floor has 1 master king, 1 queen, 1 office Basement has 2 queen rooms and 1 room with a bunk bed and a twin bed. Unwind in the inviting hot tub, perfect for starlit evenings & soothing relaxation. This property offers a convenient proximity to Collingwood's finest amenities, hiking trails, & ski resorts are just a short drive away, ensuring year-round enjoyment.

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Guest favourite

A sandy beach stretches out under a clear blue sky, with gentle waves lapping at the shore. A wooden pathway leads to the water, while a few people are seen walking along the beach, enjoying the serene coastal atmosphere.

Villa in Tiny

4.9 out of 5 average rating, 166 reviews

Beautiful Getaway Location - Cuddles Cove

Enjoy a all year round getaway either personal or corporate retreat at this spacious, well equipped Bungalow located short minutes walk from beautiful sand beach access. This newly built cottage is approx 5,000 Sqft with an additional 1,000 Sqft covered balcony offering accommodations of 6 queen beds, 1 Luxury full kitchen, 1 BBQ and lots of entertainment! Enjoy a nice Quiet getaway in the lovely community of Tiny! STRTT-2026-135

LocationFamilyHeating