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Villa vacation rentals in Simcoe County

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Top-rated villa rentals in Simcoe County

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Villa in Tiny

4.89 out of 5 average rating, 46 reviews

Chic & luxurious villa with outdoor sauna

Welcome to the Fontaine Bleu! A chic & luxurious getaway with the comforts of home and the amenities of a 5-star resort. Entertain friends & family in our show-stopping Chef’s kitchen. Indulge in the beauty & serenity of each bedroom. Relax your senses in our cedar sauna or tell stories & gather around the firepit. Challenge friends & family to a curated variety of board & recreational games. Take in Canada’s most beautiful sunsets on Tiny’s sandy beaches just steps away! Licence #STRTT2022218

Villa in Aurora

4.97 out of 5 average rating, 30 reviews

6BR 6BA Luxe Aurora Oasis | 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

Villa in Bradford West Gwillimbury

4.71 out of 5 average rating, 96 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.

Villa in Gravenhurst

4.86 out of 5 average rating, 14 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!

Villa in Tiny

4.98 out of 5 average rating, 91 reviews

Spacious villa in pines

Spacious house with sauna and play room in Tiny, Lafontane, 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.

Villa in Georgina

4.93 out of 5 average rating, 27 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

Villa in Gravenhurst

4.89 out of 5 average rating, 9 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

4.95 out of 5 average rating, 21 reviews

Cedar Escape in 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.

Villa in Kettleby

4.96 out of 5 average rating, 52 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, 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!

Villa in Gravenhurst

5 out of 5 average rating, 20 reviews

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.

Villa in Oro Station

5 out of 5 average rating, 20 reviews

Oro Estate - A Secluded Private Villa on 100 acres

Welcome to The Oro Estate! Situated on the top of a hill in the middle of a dense forest. You’ll have access to the full house and 107 acres of forest with kilometers of trails. The country house is close to the New Vetta Nordic Spa, Horseshoe, Hardwood, and Blue Mountain ski resorts, provincial parks, Simcoe County trails (biking, hiking, atv, snowmobile). The spacious country house offers 6000+ sq.ft of space with a large kitchen and plenty of entertainment and activities.

Villa in Tiny

4.9 out of 5 average rating, 143 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-2024-174

Vacation rentals for every style

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Kick off your hiking boots at these rustic lodgings

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Intimate homes. inviting architecture

Popular amenities for Simcoe County villa rentals

Free parking on premises

Air conditioning

Private villa rentals

Villa in Aurora

New place to stay

Entire Single House 5300ft² Self Check-in/out

Villa in Innisfil

4.67 out of 5 average rating, 9 reviews

4Bedroom Elegant LakeViewCottage

Villa in Collingwood

4.79 out of 5 average rating, 84 reviews

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

Luxury villa rentals

Villa in The Blue Mountains

4.96 out of 5 average rating, 25 reviews

The Blue Mountains New Villa

Villa in Wasaga Beach

4.09 out of 5 average rating, 22 reviews

Beach1*com - Riverfront Resort - Villa #32

Villa in Whitchurch-Stouffville

4.65 out of 5 average rating, 23 reviews

Luxury countryside/Forest Villa (close to lake)

Villa in Oro Station

5 out of 5 average rating, 20 reviews

Oro Estate - A Secluded Private Villa on 100 acres

Villa rentals with a pool

Villa in The Blue Mountains

4.96 out of 5 average rating, 25 reviews

The Blue Mountains New Villa

Villa in Gravenhurst

4.86 out of 5 average rating, 14 reviews

Luxury Modern Muskoka Retreat

Villa in Gravenhurst

4.83 out of 5 average rating, 6 reviews

Nordic Elegance Villa in Muskoka

Villa in Gravenhurst

New place to stay

Villa On The Green

Villa in Gravenhurst

4.89 out of 5 average rating, 9 reviews

ScandinaVilla Retreat

Villa in Gravenhurst

5 out of 5 average rating, 6 reviews

GavenScape a Luxury 3 Bedroom Villa

Villa in Whitchurch-Stouffville

4.95 out of 5 average rating, 21 reviews

Cedar Escape in 10-Acre Private Forest

Destinations to explore