Smoking friendly holiday rentals in Simcoe County

Bed of Roses Airbnb. Hot tub! 45 mins N of Toronto

*Requests typically replied to within 15 mins during the day.* Private bright 2 bedroom basement (sleeps 4 & no shared areas), 45 minutes N of Toronto. We live in a safe neighbourhood, in a home which backs onto a forest. Walking distance to a train station and a very large mall. You will have two private bedrooms, your OWN bathroom and full kitchen, 3 fireplaces, internet & HOT TUB! Separate entrance. No parties. No instant booking. We screen our guests as we live upstairs with our kids.

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.

Romantic Spa/Sauna Cabin Getaway

This unique 'off grid style' is a tiny cabin surrounded by nature & panaramic views. Hosted on the lands of WÄRME Wellness- A SPOT TO RETREAT, relax & endure much needed downtime : by yourself, a couple/ two family members/friends who are looking for spa quality time 'away from it all.' Inside - enjoy the benefits of sauna/spa culture w/ an authentic large wood powered sauna. Bathrooms are located adjacent to cabin. Yoga studio available for rent. Ask about our ‘elevated romance package.’

Newly Renovated Spacious 2BR Home Near Yonge St

Welcome to your bright and modern 2-bedroom guest home in Newmarket, just a short walk to Yonge St and close to shopping, restaurants, and Main Street. This private basement suite offers a comfortable, well-appointed stay in a quiet neighbourhood, with a separate entrance, driveway parking, fast Wi‑Fi, in-suite laundry, and a brand-new modern kitchen. Ideal for families, couples, business travellers, and longer stays, the home combines comfort, convenience, and privacy in a peaceful setting.

Quiet Waters Getaway

Step onto this cozy modern cottage tucked away on the waters of Waubaushene Ontario. Drop a fishing line off our 100ft+ dock, or take a paddle on the lake! Warm up next to the fire under the netted gazebo, or roast marshmallows over the second fire pit under the stars. As we move into the colder month’s Mount St. Louie ski hill is a short drive away from our winterized space. Whatever adventure you choose to do, create those memories with your friends and family at our Quiet Waters Getaway!

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.

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

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.

Hot Tub & Sauna Retreat by Georgian Bay Trails

Welcome to Eagle Point Cottage, a modern-chic escape nestled along the scenic Tay Trail and Georgian Bay. 🥾Backs onto the scenic Tay Trail and Georgian Bay 💧Private hot tub and stand alone sauna building 🔥Natural gas BBQ and firepit in a quiet, fenced backyard 🌐High-speed Wi-Fi throughout the house 🛏️Sleeps 6 guests in the main house + 2 guests in a heated/cooled bunkie