Pet-friendly holiday rentals in Simcoe County

Whispering Pines Cabin in Woodland Acres

Experience this nature retreat just 60 km from Toronto and feel like you’re thousands of miles away. The perfect glamping experience for any nature lover looking for a relaxing getaway. There is power in the bunkie which offers the convenience of lighting, cell phone charging, an electric fireplace, a kuerig coffee maker and mini fridge with freezer. Pursue your favourite outdoor activities during the day and then return to your cozy queen size bed and sofa bed just steps away from the bonfire.

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.

Country Cabin Escape | King Bed | Pet Friendly

Tucked away on our peaceful family farm, this private retreat offers tranquility and comfort—while not secluded in the woods, it provides a true countryside experience. ✨ Full kitchen 🔥 Wood fire pit & propane BBQ 📶 WiFi + 40” Smart TV 🚿 Cozy 3-piece bathroom 🧺 Laundry access 🌲 Scenic walking trails Located near our farmhouse, Country Suite, and Event Barn, the cabin remains fully private with blinds for added comfort. We look forward to welcoming you for a restful and memorable stay!

Relax at The Rock: Muskoka Waterfront Cottage

Enjoy fishing, swimming and paddling 22km of the green and black rivers. Paddleboat, canoe, 2 kayaks, and a SUP provided. Take the short 5 minute stroll into town for ice cream or fresh baked treats. Lay out on the elevated deck or in the screened in porch with a good book. End your evening at the riverfront firepit. Nearby day adventures include hiking, golfing, parks, beaches, breweries, casino rama, and downhill skiing at Mount St Louis Moonstone and Horseshoe Valley (30 minute drive).

Private Loft w Sauna, Fireplace, Wi-Fi & Projector

Welcome to the LOFT - A private, eclectically designed spa-inspired unique stay in the historic Webb Schoolhouse, less than an hour from Toronto. Featured in TORONTO LIFE in 2021, this private loft includes a sauna, unique hanging bed, wood stove, kitchenette and is filled with art, and huge tropical plants as well as a projector & giant screen for epic movie nights. Relax and recharge, roam the grounds and enjoy the beautiful outdoor spaces, the permaculture farm, animals, and fire pit.

Cozy & Private Guest Suite in Stayner, Ontario.

PLEASE READ THE DESCRIPTION In "The Space" BEFORE BOOKING. The space DOES NOT HAVE A SHOWER. We are a proud Superhost destination close to Wasaga Beach (15-20 mins), Collingwood (20-25 mins) and Blue Mountain Village (30-35 mins.) The place is super cozy. You'll love the location, the privacy, the amenities, the hosts and the value. This place is fabulous for couples, solo adventurers, business travellers, and canine companions. Please let us know if you are bringing a dog with you

Deerleap Glamping Dome

Located close to the city, our four-season glamping dome offers a peaceful and unique escape. In winter, the snow-covered landscape creates a magical scene, while inside, the wood pellet stove keeps the dome exceptionally warm and cozy. Nestled on 10 acres of picturesque land and a stunning pond view, Enjoy everything you need—from upscale sanitary facilities to fast Wi-Fi. Whether you’re celebrating a birthday, an anniversary, or simply seeking quiet time in nature.

Modern Condo at Friday harbour/Pet Friendly

Welcome to Our Elegant Property We're driven by a genuine passion for creating exceptional guest experiences. Our goal is straightforward: to exceed your unique needs and desires during your stay. More than just providing a place to stay, we want to make your visit memorable and enjoyable. Feel free to reach out if you have any questions. We're here to ensure your stay is comfortable and stress-free. **Additional fees are applied for long term stays**

Private 40 Acre Cottage with Hot Tub

Our two bedroom cabin + cubby (available in summers) by a scenic pond is a private getaway while close to the main road and many amenities. Private outdoor space includes hot tub, deck, fire pit, and walking trails. We have a barn with ping pong and foosball tables. We are 20 min to Barrie, 10 min to Midland, 20 min to Balm beach, Wasaga beach, Mt. St Louis and Horseshoe Valley resort.