Holiday home rentals in Simcoe County

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Top-rated holiday home rentals in Simcoe County

Guests agree: these holiday home rentals are highly rated for location, cleanliness and more.

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A brick duplex house is displayed against a clear blue sky, surrounded by greenery. The structure features multiple windows, a front door, and a driveway leading towards an outbuilding in the background. Well-maintained grassy areas are present in the front yard.
Holiday home in Midland
4.82 out of 5 average rating, 33 reviews

Cheerful 3 bedroom fully equipped vacation home

Your family will be close to everything when you stay at this centrally located place. All you need is walking distance including Midland Harbour, downtown with great restaurants and boutique shopping and little lake park. 5 minute drive to malls and shopping, 20 minutes drive to many tourist attractions and beaches. This is the main unit in a duplex house. Basement unit occupied by one senior person that enjoys having visitors on the main unit, does not interfere with activities of guests.

Guest favourite
A serene beach scene captures the calm water reflecting the skyline of downtown Barrie. A wooden boardwalk stretches along the shore, with people strolling in the distance. The sky showcases a soft gradient of morning light, enhancing the peaceful ambiance of the location.
Holiday home in Barrie
4.87 out of 5 average rating, 54 reviews

Vacation Home in Barrie

International tranquil haven and excellent location in downtown Barrie, ON, Canada. I can provide 2 bedroom, 1 1/2 bathroom, a very comfortable living room and kitchen with everything in. The backyard is perfect to relax, bbq, lunch or dinner + fresh air. From the house it‘s walking 5 minutes to beach front of water. Inside the house no smoking. Free internet and 1-2 parking space. Stair lift up to 110kg. Your family will be close to everything when you stay at this centrally located place.

An aerial view showcases the Sunset Villa positioned near a sandy beach. The three-bedroom cottage with a peaked roof is surrounded by trees, with clear roads leading to it. The beach area is visible in the foreground, with gentle waves meeting the shore.
Holiday home in Wasaga Beach
4.59 out of 5 average rating, 32 reviews

Lovely & Charming 3 Bedroom vacay home

Ideal for families, This beautiful Cottage provides a quiet and relaxing atmosphere within the hustle and bustle of one of Ontario's most popular resort towns, Wasaga Beach. The area's many forms of entertainment for people of all ages, from swimming, golfing, go-carting, paint ball, hiking, biking, sea-doo rentals and fishing charters to dining, quiet walks and spectacular sunsets. blue mountain is only 15 minutes drive. Bring your snowmobile with you, you can drive it on the street.

Top guest favourite
A bright bedroom layout features two double beds adorned with white linens and green accents. A small seating area is visible, including a gray chair and decorative plants. Adjacent, a second room presents a king bed with navy walls, complemented by stylish wall art and plush cushions.
Holiday home in Barrie
5 out of 5 average rating, 56 reviews

Entire House, Luxury Cozy Family Retreat w/ 5 Beds

Welcome to our stunning modern house in the serene west end of Barrie. This beautifully decorated home boasts 4 spacious bedrooms, each equipped with 5 cozy, hotel-quality beds. Ideal for families, friends, or business travelers, our home offers a perfect blend of comfort and convenience. Each bedroom boasts unique decor, providing positive vibes and a calming atmosphere. Located close to the Waterfront, ski resorts, parks, and local dining. 📩 Message us for an exclusive discount!

Guest favourite
Holiday home in Port Severn
4.89 out of 5 average rating, 9 reviews

Picturesque Muskoka cottage with amazing shoreline

Discover the beauty of Muskoka's Honey Harbour at this privately owned waterfront property with road access. The cottage has a unique waterfront perfect for lounging around or playing activities. The cottage boasts a new kitchen and cozy living room with panoramic lake views, sunsets and a wood burning fireplace. Great fishing, canoe, kayak, deck, fire table and shoreline firepit make your stay extra special. Tons of parking, a boat launch and a dock to accommodate your boat.

Superhost
A wooden dock is positioned beside calm waters, featuring a small boat tied up at the edge. Two red chairs are placed on the dock, framed by lush greenery and trees that reflect in the water, creating a serene atmosphere.
Holiday home in Bracebridge
4.82 out of 5 average rating, 50 reviews

Newly Renovated Cottage in the Heart of Muskoka

This 4 seasons waterfront cottage is under 2 hours away from the GTA. Come unwind in our cozy two story cabin completely surrounded by nature. Enjoy complete privacy with no visible neighbors on either side without sacrificing any modern amenities, as our retreat has been recently updated for your comfort. Though nestled in the great outdoors, this cottage is just 10mins away from the vibrant town of Bracebridge; where there is no shortage of great restaurants & coffee shops.

Guest favourite
Holiday home in Midland
4.82 out of 5 average rating, 62 reviews

Georgian Bay retreat - apartment in Midland

Enjoy a fantastic Gateway in my lovely, raised basement apartment with tons of natural light and only a few minutes away from Georgian Bay and the best sandy beaches in Ontario. Great location to access Midland Waterfront, park beside the Little Lake, various beautiful trails. Walk to downtown to quiet coffee shops, restaurants, Sunday farmers market, ice cream shop. This is an Ideal place for outdoor enthusiasts, skiers, cyclists, hikers, and shop goers!

A vibrant garden features a variety of flowers and greenery, artfully arranged around natural stone elements. A few small trees and shrubs add to the lush landscape, with distant views of rolling hills visible under a partly cloudy sky.
Holiday home in Creemore
4.2 out of 5 average rating, 15 reviews

The Creemore Retreat, A Private Wonderland

This is the unique getaway you've been looking for! This special home is nestled in 6 acres of property that contains two ponds suitable for swimming or small boats, llandscaped lawns and gardens, and distant views of the rolling farmland and forests of Simcoe County. Close to all the pleasures of Georgian Bay in the Wasaga, Collingwood and Blue Mountain area, you can enjoy swimming, hiking, biking, boating, fine dining and exploring, all just minutes away.

Guest favourite
A two-story cottage structure features expansive glass walls and a spacious deck adorned with soft ambient lighting. The natural wood exterior is complemented by strategically placed outdoor lighting, enhancing the home's inviting presence amidst surrounding trees.
Holiday home in Gravenhurst
4.93 out of 5 average rating, 30 reviews

Muskoka Charm-Beautiful four bedroom cottage

Amazing opportunity to create lifelong memories in a year round cottage on Lake Muskoka in the heart of the Muskoka's. Situated on 125 feet of Lake Muskoka shoreline, Muskoka Charm offers sought after privacy and picturesque scenery. This newly renovated 4 bedroom cottage, 2 bathroom home is less than 8 km to the Wharf and downtown of Gravenhurst. Highlights include a brand new post and beam Muskoka room, brand new Hydropool self cleaning hot tub!

Holiday home in Gravenhurst
4.88 out of 5 average rating, 8 reviews

A charming 3 bedroom getaway in Muskoka

Located just a two minute drive (15 minutes walk) from a private sandy, shallow beach, this fully renovated three-bedroom vacation home (first floor only) is ready for your perfect family retreat. All creature comforts are available as you surround yourself with trees at the forest's edge while enjoying views of large Muskoka rock croppings. Watch deer and Ontario barred owl make guest appearances on the property.

Superhost
Holiday home in Ravenna
4.49 out of 5 average rating, 136 reviews

The Beehive w/ Hot Tub, Sauna & Fireplace

The Beehive is a Blue Mountain landmark. This dome-shaped chalet is adorable & Instaworthy! Compact and cozy inside, the chalet has 6 bedrooms + a sofa bed accommodating groups of up to 14 guests. The circular living room in the loft is a unique space to gather and connect. Conveniently located at the top of the North Chair & just minutes away from Scenic Caves & Blue Mountain Village.

Superhost
The exterior of a well-structured building is shown, featuring a combination of stone and wood materials. Two white doors are positioned centrally, framed by large windows on either side. A triangular roof with a distinctive logo is visible, and the surrounding area is landscaped with trees.
Holiday home in Wasaga Beach
4.67 out of 5 average rating, 9 reviews

Whole Building Beach 1 Suites of Wasaga

Beach Area 1 - Walk about 3-5 minutes to main strip at Beach Area 1. Whole building provides privacy for all your guests at one location. Accommodates up to 16 people max. Enjoy easy access to everything from this perfectly located home base.

Popular amenities for holiday home rentals in Simcoe County

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