Smoking-friendly holiday rentals in Oro-Medonte

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.

Accessible Luxury Riverside Beauty!

Welcome to your dream getaway on the serene Severn River — a completely renovated, designer-owned home created with love by a mother for her quadriplegic son. Every inch of this stunning space was reimagined to be both fully accessible and breathtakingly beautiful — a seamless blend of function and style where you’d never guess a wheelchair was part of the design. Enjoy panoramic views of boats gliding by from nearly every room, or unwind on the expansive deck as the sun dances on the water.

Chic 2BR Spacious 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!

Cozy little apartment in Wasaga Beach.

The Little Bluebell . The apartment is cozy and private. It has a queen size bed and a sofa bed. We are pet friendly, but if bringing a dog please don't leave it unattended for hours. A little beach is a 5 minute walk where you can enjoy some time by the water. 10 minute drive to main end of Wasaga Beach. 25 minutes to Blue Mountain. No parties or loud music . Please don't open the back door in the apartment. There are 2 dogs in the back yard and don't want them to escape. Thank you.

Hot Tub & Sauna Retreat by Georgian Bay Trails

Sunset s'mores by the firepit, morning paddling from your doorstep, and evening soaks in your private hot tub—Eagle Point Cottage is where Georgian Bay weekends become unforgettable memories. This modern cottage sleeps 8 (4 bedrooms + heated bunkie), sits steps from the Tay Shore Trail and public beach access, and comes fully equipped with a sauna, kayaks, canoe, and board games. Superhost Stephen averages 4.83 stars across 185 guest reviews. Ready? Reserve your dates today.

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. Please note the apartment is accessible by stairs only.

Luxe Modern Retreat - Theatre, Hot Tub and Bar

Welcome to an extraordinary luxury home in Orillia - a rare, fully upgraded designer home intended to deliver an unforgettable five-star experience. This is not your typical Airbnb. Every inch of this home has been thoughtfully curated with premium finishes, high-end amenities, and entertainment-focused features. So whether you’re planning a weekend getaway, family retreat, or group experience, this property delivers a true five-star atmosphere.

Shadow

Welcome to Shadow—your cozy escape overlooking peaceful Lake Muskoka. This newly built 2-bedroom, 1-bathroom, 1-bunky cottage offers warm, inviting interiors and a beautiful Muskoka room perfect for morning coffee or quiet relaxation. With stunning lake views and comfortable charm throughout, Shadow Shack is the ideal place to unwind and enjoy Muskoka at a slower, sweeter pace. Making your stay the perfect little getaway !

Ground Floor w/ Large Terrance @ Friday Harbour

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 4-5 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

Modern 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.