Villa holiday rentals in Simcoe County

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.

Spacious villa in pines

Spacious house with a Play Room on Georgian Bay, LaFontaine, 3-4 min walk to the beautiful beaches. It's a great families retreat in a quiet neighborhood near the lake. Have a barbeque or glass of wine on a spacious wrap around deck with screen mosquito/flies protection or take a walk to the lake to watch amazing Georgian Bay sunset. In summer you may enjoy a boat trip to thousand islands, swimming, biking, canoeing. In winter this area is popular for snowmobiling, skiing and skating.

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!

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

The Family Escape-5 min to the slopes & the shore!

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!

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!

Entire Villa with beautiful fenced backyard

This cozy and elegant villa is situated on 0.5 acre with spacious first-floor master bedroom suite, indoor outdoor office spaces, 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. For any event or mid-term stay, please confirm with the Host prior to booking. Thanks!

Luxury Resort Villa in Muskoka

Explore the charm of Muskoka Bay Resort with this Brand New, fully furnished 3-bedroom villa! Nestled within the resort, just moments away from Lake Muskoka and Gravenhurst Wharf, this accommodation offers a serene retreat. Overlooking the Golf Course, you'll relish in breathtaking views. Unwind with loved ones in this inviting haven, boasting all the comforts of home. From golfing and fishing to skiing and outdoor saunas, there's a plethora of activities to enjoy in the area.

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-2025-152