Smoking friendly holiday rentals in Simcoe County

Incredible retro on beach with incredible views

This is a original retro 1940’s cottage on the most beautiful private Beach with huge new deck and new windows and patio sliding doors and has the best views on the Beach in wasaga beach.while staying at this retro gem you will smell the real pine vault ceilings ..inside the cottage or out side will have the sense that you are kings and queens of this amazing Beach front location. 5 minute walk to new casino and casino restaurant and close to pickle ball courts…This could be your dream vacation

Lakefront family cottage on Sparrow Lake

Enjoy unforgettable sunsets at our four-season Sparrow Lake cottage, just 90 minutes from Toronto, between Orillia and Gravenhurst. This retreat offers water fun, peaceful moments by the fire, and great fishing. Relax with your family or two families in this serene setting, featuring a wrap-around deck, lake views, private dock for swimming and fishing, and plenty of space for activities. In peak season (July–August), rentals are 7 days or longer. Shorter stays are welcome the rest of the year.

Serenity, Simplicity and Stone

This is a tiny cottage in a sleepy little hollow that opens onto the Georgian Bay. Inside, each stone was carefully chosen and the woodwork was built, piece by piece, by two craftsmen who are highly skilled and passionate about repurposing. It's an art that will leave you in awe; especially if you're worried about climate crisis. The coat hangers are upcycled 100-year-old railway spikes! If you're looking for luxury you will be disappointed but if you're a minimalist you're going to love it.

JJ’s small town country retreat

Take a step back in time to this old farm house. Located on the corner of our little town called Badjeros. This house was built in the 1930s and it’s been in our family for over 80 years. Since then there has been numerous upgrades to the house as well as a large 1200 square foot open concept addition built onto the existing house. While out in the country, this house is central to many attractions in the area 1.5 hours south of Toronto/GTA. Blue Mountain/ Collingwood is 30 minutes north.

Luxurious Muskoka Home | Serene Spacious Comfort

Welcome to your dream Muskoka escape! Nestled in the heart of Gravenhurst, this stunning modern home offers the perfect blend of luxury, comfort, and natural beauty. Ideal for families, couples, and groups seeking a serene getaway, our property provides an unforgettable experience in Ontario's renowned cottage country. *** PLEASE NOTE: If you are requesting fewer nights than our minimum stay, please message us directly and we will do our best to accommodate. ***

Farm House Resort Stay Pool Hot Tub

Make some wonderful memories at this unique family & pet friendly modern Farmhouse! Backyard oasis to spend a lazy day relaxing in the salt water pool and hot tub. Master suite has jacuzzi tub and private balcony. Wrap around porch for a glass of wine or morning coffee. Catch the breeze under the barn beam pergola. Toast a few marshmallows over a warm campfire and check out the stars in the clear night sky. Games exercise room. Great location ample parking

Friday Harbour Ground Floor w/ Large Terrance

Welcome to FriYAY Getaways at The Friday Harbour Resort! Create unforgettable memories in our unique family-friendly condo. Beautifully designed, Two sets of cozy bunk beds, along w/a Queen bed & trundle.Accommodates 5-6 Adults 2-3 children. Each room is equipped w/a smart TV, offering access to Disney,Amazon Prime,& Netflix. Our backyard patio is perfect for entertaining, featuring a BBQ w/a pizza oven & griddle

Private Log Cabin with 7 beds, 2 futons + hot tub

Forget your worries and enjoy the beautiful nature and the variety of wildlife in this spacious and serene space. Enjoy the outdoor shower on hot summer days. taking in the amazing night skies, perfect for star gazing in or out of the hot tub. Creemore and its brewery are close by, we're not far from Wasaga Beach or Blue Mountain and Collingwood so there's something for everyone and all seasons.

Lake Simco penthouse at Friday Harbour resort

Modern penthouse at Friday Harbour Resort offering a luxurious and relaxing escape. Enjoy stunning sunsets from the spacious balcony with BBQ, fireplace, and comfortable lounge area. Beautifully furnished with access to premium resort amenities. Perfect for couples or solo travelers seeking comfort, style, and a peaceful getaway surrounded by nature, water, and upscale dining.