Smoking-friendly holiday rentals in Oro-Medonte

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.

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.

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!

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!

Farmhouse GUEST SUITE; Year round hot tub

Unique Farmhouse stay in modern Guest Suite Fully stocked kitchenette Bedroom/Livingroom Suite - sleeps 4 Ensuite bathroom with shower Wrap around porch for a glass of wine or your morning coffee. Year round hot tub. Firepit - toast a few marshmallows over a warm fire and check out the stars in the clear night sky. Horses may not be visible in all months. 1 QUEEN BED 1 QUEEN PULL OUT COUCH Winter: On snowmobile trail close to ski hills, hot tub EVENTS are not permitted.

Shanty Bay Escape

Escape to a cozy retreat by Lake Simcoe, just minutes from downtown Barrie. Enjoy stunning lake views, a sandy beach steps away, and a spacious backyard for dining, lounging, and campfires. Inside, the cottage features an open-concept living area, a full kitchen, and cozy bedrooms. Perfect year-round for adventure or relaxation, with skiing at Snow Valley and Horseshoe Valley nearby, plus local spas like Hand & Stone and Healica for ultimate relaxation.

Tiny hideaway campsite

No tent included but a beautiful spot to set up your own or park your camper for the weekend. Outdoor seating area and fire pit included. Firewood for purchase. View of a small pond and walking trails on site. Awenda park is just around the corner and minutes to historic Penetanguishene. Come see what adventure awaits! - No showers but beautiful outhouse provided. - pets are allowed but MUST be on leash at all times.

Peaceful country getaway

A beautiful above-garage apartment with huge windows and a spacious, open concept main living area encourages connection and comfort. Our space is ultra family friendly with an abundance of games, puzzles, and toys for kids but has everything the adults need to have fun as well. Surrounded by farmland, you'll enjoy watching the sun set off the back deck and be able to truly unwind in the private and peaceful setting.

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

Luxury 6BR Retreat in Horseshoe | Pool + Hot Tub |

Gather your family, friends, or colleagues for the ultimate Horseshoe Valley escape. This 6-bedroom, 3-bath modern retreat features a pool, hot tub, fireplaces, and two living spaces for relaxation and entertainment. Perfect for family reunions, group getaways, or business retreats, the home offers bright interiors, stylish finishes, and thoughtful touches, all close to nature and top local attractions.

Waterfront Beach House in Waubaushene

Relax with the whole family. Waterfront location is ideal for a fun summer get away. The property faces Georgian Bay and backs onto the Tay Shore trail where you can walk/bike. Private beach and beach toys with lots of space to chill Water front fireplace and decks to relax and watch the sunset. 15 minutes from local attractions like Saint Marie of the Huron and Matyrs Shrine and Town of Midland