Holiday home rentals in Simcoe County

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.

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.

1(B) Bedroom Apt in 3 unit Bldg Right on the Beach

(2Adults+2kids max) Take a break and unwind at this peaceful oasis. This beautiful Cottage/unit 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. 1 car parking spot.

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!

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.

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.

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!

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.

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!

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.

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.

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.