Vacation home rentals in Simcoe County

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Top-rated vacation home rentals in Simcoe County

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Top guest favorite
A modern living space is presented, featuring a large kitchen island with bar seating. A comfortable couch, accented with decorative pillows, is positioned near a wall showcasing circular wall art. Natural light floods the area through expansive windows, creating a bright atmosphere.
Vacation home in Innisfil
5 out of 5 average rating, 50 reviews

Innisfil Resort - 3 Bed Condo Amazing Views

Make some memories at this unique marina/boardwalk neighbourhood. It is a family-friendly place 4 season getaway, with lots of activities, walking trails, bike rentals, water sport rentals, entertainment and fabulous restaurants. 3 bedrooms, 2 bathrooms, modern kitchen with large island, big comfy couch! Enjoy the extra large South East Balcony over looking the Marina and the Boardwalk. Comes complete with a fully stocked kitchen, bbq and parking. You will feel right at home on your getaway.

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.
Vacation 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.

Top guest favorite
A modern kitchen and dining area features sleek cabinetry and stainless steel appliances. A cozy electric fireplace is positioned beneath a wall-mounted TV. The dining table is set for four, with tableware arranged neatly. Soft lighting illuminates the space, highlighting a blend of textures and materials.
Vacation home in Orillia
4.99 out of 5 average rating, 183 reviews

Days Away! free parking - no cleaning fee

Welcome to Days Away! Hosted by Lisa and Brad Day. Our city and surrounding areas have so many events, attractions and seasonal activities. We love to explore so we know all the wonderful hidden gems. It is a central/convenient location. We entered hosting because we love to entertain and participate in local events/activities. Whether you are here for sports, attractions, festivals... We want to share this amazing area with you. Come stay with us and let us exceed your expectations!

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.
Vacation home in Wasaga Beach
4.58 out of 5 average rating, 31 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 favorite
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.
Vacation home in Barrie
5 out of 5 average rating, 44 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 favorite
Vacation 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.
Vacation 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.

Superhost
The exterior of a multi-level apartment building features a blue color scheme with white trim. Balconies adorn the upper levels, while stone accents complement the entrance. A pathway leads to a set of wooden stairs, connecting the building's three levels.
Vacation home in Oro
4.8 out of 5 average rating, 25 reviews

Spacious Fully Furnished 1-Bedroom Apartment

A four season apartment located in the heart of Horseshoe Valley Ski Hills, just 15 minutes from Barrie - A perfect destination for any getaways with your friends and family! The surrounding area offers an amazing variety of activities for the whole family: mountain biking, hiking trails, picturesque golf courses, alpine and country cross skiing. You will also have a chance exploring nearby shops, dining or outing to the beach, waterpark or Elmvale Jungle Zoo.

Guest favorite
Vacation home in Gravenhurst
4.96 out of 5 average rating, 55 reviews

Spacious Muskoka 6 Bedroom Forest Getaway

Unwind on 50 acres of private Muskoka forest, complete with a scenic pond, backyard fire pit, and plenty of space to roam. This spacious 6-bedroom, 3.5-bath retreat is perfect for families and groups. Enjoy a fully loaded game room with billiards, fooseball, ping pong, plus TV in every room. Outdoors, relax by the fire, let the kids enjoy the play area, shoot hoops, or take in the fall colors. Fast Wi-Fi included — perfect mix of comfort, fun, and nature.

Superhost
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.
Vacation home in Gravenhurst
4.93 out of 5 average rating, 27 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!

Vacation 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
An expansive chalet is set against a clear blue sky, featuring a large patio area paved with stones. The structure showcases multiple windows and a second-floor balcony. Surrounding greenery contributes to the tranquil outdoor environment, enhancing the overall spacious feel of the property.
Vacation home in Ravenna
4.66 out of 5 average rating, 113 reviews

Paradise Manor: Hot Tub + Sauna + Games

This spacious 6 bedroom chalet is located just under a 5 minute walk to the top of the north chair lift. The chalet is located in a community of Blue Mountain know as Swiss Meadows. The community borders the tops of the chair lifts, no need to fight for parking, you can either walk to the north chair or park in one of 2 low traffic lots.

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