Smoking-friendly holiday rentals in Oro-Medonte

Guest suite in Wasaga Beach

4.78 out of 5 average rating, 36 reviews

IRIE Paradise Beach Cottage

Welcome to Irie Paradise, your home away from home. Relax with the entire family at our comfy four season home. In the summer enjoy a short walk to Ontario's longest freshwater beach. Take a walk along white sandy beaches, great for children with it's shallow shores or watch a spectacular sunset during the evening. In winter months, you may enjoy exploring our picturesque communities less than 30 mins away. You will find beautiful scadinavian Blue Mountain for all snowboarding & spa luxuries.

4.95 out of 5 average rating, 22 reviews

Apartment in Orillia

Cozy Apartment on 20-Acre Haven (no cleaning fee)

Escape to our bright, comfortable, and well-equipped lower level apartment just outside Orillia. Wander our 20 acre retreat featuring a pond and a serene clearing with firepit. Enjoy the outside guest seating area with barbecue and luxuriate in the outdoor shower. Hot tub available on request. Enjoy direct access to scenic trails perfect for biking and hiking, with a quick 10-minute commute to Orillia by car or a leisurely ride along the trail. Plus, explore the nearby Simcoe County forest.

4.73 out of 5 average rating, 117 reviews

Cottage in Wasaga Beach

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

5 out of 5 average rating, 12 reviews

Cottage in Gravenhurst

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.

Cottage in Victoria Harbour

4.82 out of 5 average rating, 206 reviews

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.

4.88 out of 5 average rating, 17 reviews

Villa in Gravenhurst

Luxury Modern Muskoka Retreat

Exquisite Scandinavian-style private villa surrounded by a lush forest landscape. Situated on the grounds of the Muskoka Bay Golf Resort, this 5 star property won’t disappoint. RARE special corner villa with walls of windows. Only two in the entire community. Enjoy the infinity pool (May-Oct), tennis, trails, golfing or just a lovely bonfire overlooking the hilly landscape. Don’t forget to visit the clubhouse and all its amenities including state of the art gym & 5 star dining experience!

4.93 out of 5 average rating, 14 reviews

Villa in Gravenhurst

Nordic Elegance Villa in Muskoka

Welcome to Nordic Elegance Villa at Muskoka Bay Resort! This villa showcases Scandinavian design and offers a sophisticated ambiance. As a 5-star property, it is designed to exceed your expectations, with amenities tailored for families. Explore a wide array of Muskoka Bay Resort's amenities, including a swimming pool, sauna, trails, and golfing (ranked #1 golf course in Ontario). Minutes away from local parks and Muskoka Steamships/Discovery Centre. Bring the family and enjoy all the fun!

5 out of 5 average rating, 9 reviews

Home in Gravenhurst

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. ***

4.83 out of 5 average rating, 12 reviews

Home in Minesing

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

4.85 out of 5 average rating, 97 reviews

Cabin in Hawkestone

Blue Dreams Of Lake Simcoe

Welcome to "Cabin Dreams Of Lake Simcoe" - your cozy blue cabin retreat in the heart of Hawkstone, Ontario, Canada. Immerse yourself in nature while enjoying modern comforts and nearby attractions. Our newly renovated 1 bedroom, 1 bathroom offers a unique getaway for couples, located just 1 1/2 hours outside of Toronto. **PLEASE NOTE** **Stairs leading up to the bed room loft are steep and may not be suitable for guests with mobility issues**

4.94 out of 5 average rating, 31 reviews

Cabin in Beaverton

Riverside Cabin Getaway

Surrounded by cedar trees and nestled along the Beaver River, come make memories at our unique getaway. Three cabins make up the accommodations, one with a kitchenette & seating area, one for sleeping and one for showering. This is a glamping experience. We provide the basics to ensure you experience the best that nature has to offer. Fishing, kayaking, hiking, relaxing... the perfect pairing of nature and upscale camping!