House holiday rentals in Simcoe County

4.88 out of 5 average rating, 108 reviews

A modern living area is highlighted by a sleek, electric fireplace beneath a large flat-screen TV. A rustic accent wall features wooden panels and decorative art. A comfortable gray sofa and a table set for dining complete the welcoming space, complemented by blue and natural tones.

Home in Innisfil

2 Bd Boardwalk Condo Patio Oasis

The ultimate boardwalk escape, just an hour away from Toronto! This modern and stylish 2-bedroom condo is perfect for a relaxing getaway, featuring an indoor fireplace and an 75" TV for cozy nights in, as well as a stunning outdoor patio oasis for enjoying the fresh air. Step outside and explore the vibrant boardwalk or simply unwind in your private outdoor haven. → Prime boardwalk location on the main level → Underground Parking → Fully equipped + stocked kitchen → Unlimited Coffee & Espresso

A bright living area features a comfortable sectional sofa adorned with patterned cushions. A natural wood dining bar with stools is positioned next to a modern kitchen. Large windows invite natural light, revealing a fenced outdoor space with greenery.

4.94 out of 5 average rating, 105 reviews

Cozy Barrie Getaway①New 3BR Private Backyard 2car

Cozy 3-Bedroom Townhouse Bright, warm, and filled with natural light, perfect for family trips and short getaways! Free parking for 2 cars. Fully stocked kitchen with island-style dining. Large smart TV and High-speed WiFi. Short drive to the beach and skiing. 👇 Please expand to see full details! 👇 ✔️ Suitable for family and business travel ✔️ Safe, quiet neighbourhood with nature view ✔️ Easy access to highway, shopping and restaurants ✔️Near golf and spa 👉Book now and enjoy a cozy stay!

4.97 out of 5 average rating, 173 reviews

A vibrant garden showcases a variety of colorful flowers, with a prominent rock identified by the number 14. Lush greenery surrounds the area, adding to the inviting outdoor space in front of a brick house. Well-maintained lawns complement the floral displays.

Home in Penetanguishene

White Rolling Sands of Penetang by Theatre

Shores of Georgian Bay - enjoy a firepit in the backyard of a deep lot backing onto woods with trails. Local walking and cycling routes, vege and flower gardens from private sunny back deck. Fully licensed and located close to Kings' Wharf Theatre / Discovery Harbour. Experience the natural beauty of Tiny Beaches, Georgian Bay Islands N.P and Awenda P.P. nearby (Park pass available for use). Marinas, beaches, boat cruise of the islands, Ste Marie Among the Hurons and Wye Marsh (Midland) nearby.

The living room features two spacious sofas adorned with soft throw pillows, complemented by glass coffee tables. A large piece of abstract artwork hangs above, while natural light filters through the large windows, enhancing the bright ambiance of the space.

4.9 out of 5 average rating, 129 reviews

Cozy main floor apartment with backyard in Barrie

Welcome to Your Cozy Retreat in Barrie! Tucked away in a quiet neighborhood, our modern main-floor apartment offers the perfect mix of comfort, style, and convenience. Relax in your private backyard with a gazebo and BBQ, cook in a fully equipped kitchen, and stay connected with high-speed Wi-Fi. Just 5 minutes from Lake Simcoe and 3.5 km from the GO Station, you’ll enjoy easy access to both nature and the city. Perfect for short getaways or longer stays — everything you need to feel at home.

A dining area features a wooden table surrounded by high-backed blue chairs. A large television is mounted on a feature wall, while crystal chandeliers hang from the ceiling. A pool table is visible in the background, enhancing the inviting atmosphere of the space.

4.96 out of 5 average rating, 101 reviews

Pool Table 10MinsToLakeSimcoe King Beds ProfDesign

Luxury! Pool Table! 75" Smart TV! Thoughtfully curated design! Unleash your inner chef in the gourmet kitchen with a gas stove, all your cooking & baking needs. Bask in the lofty 10' ceilings, and explore the vibrant neighbourhood with top-notch restaurants, shopping, golf courses, driving range, Hwy 400, serene lake and beach access, all within 5-10 mins. 25 Mins from Snow Valley & Horseshoe Valley Resort. Your luxurious escape awaits! 2 King Beds, 4 Queen Beds, 3 Single Pullout Mattresses!

4.91 out of 5 average rating, 263 reviews

A vibrant bar and games room is featured, with a pool table occupying the center space. An air hockey table and foosball table are visible in the foreground. Colorful decor, including flags and artwork, adds to the lively atmosphere, while red lighting enhances the playful environment.

Home in Collingwood

JJ’s Collingwood bar & games house.

Welcome to beautiful 4 season Collingwood! This house offers a 4 bedroom 2 bathroom fully detached house on a large mature lot in Collingwood. This house is a 10 minute walk to Sunset Point Beach and a 10 minute walk to downtown Collingwood. House is in a prime location approximately 10 minute drive to Blue Mountain, 20 minutes to Thornbury and 15 minute drive to Wasaga Beach. Big fenced in backyard for fires, horse shoes or whatever you would like, plenty of parking ( 4 car maximum)

4.98 out of 5 average rating, 167 reviews

A spacious living area is viewed, featuring a comfortable dark sectional sofa with plush cushions. A wooden coffee table sits nearby, with a green plant adding a touch of nature. The sleeping area includes a cozy bed and a window allowing natural light to illuminate the room.

Home in Coldwater

Luxury Guest House with Private Hot Tub and Trails

Equipped with a 4 person Hot Tub and 60 acres of Private Trails, you're sure to find tranquility in our unique Guest House. And if you're feeling more adventerous, there's lots to do in the area. From Tree Top Treking to Golfing, and Skiing in the winter of course, Oro-Medonte is truly a four season destination that is sure to capture your heart. We are pet friendly! We allow up to three pets total. It’s $50 per pet, we charge for 3 pets upfront. Rebates are issued accordingly.

4.95 out of 5 average rating, 162 reviews

A charming brick house is observed with a well-maintained front garden featuring small plants. The entrance is framed by a covered porch with a railing. Windows along the front allow natural light, and a clear blue sky is visible above, enhancing the inviting setting.

Home in Gravenhurst

Royal House Muskoka

We welcome guests to our comfortable home in Gravenhurst Ontario. Original natural wood trimmed home in the center of downtown Gravenhurst, within walking distance from downtown, Sawdust City Craft Brewery, Gull Lake beach, restaurants, grocery stores and the historic Lake Muskoka Wharf attractions . A popular year round destination in the heart of beautiful Muskoka. The hub for endless seasonal activities. Located less than 2 hours from Toronto. 4 bedrooms, 6 beds and 2 bathrooms

The exterior of a modern home is highlighted at sunset, showcasing large windows that reflect warm interior lighting. A spacious backyard features green grass, a dining area under a gazebo, and a hot tub on the deck, creating an inviting outdoor space.

4.97 out of 5 average rating, 151 reviews

Waterfront Home, City/Sunset View & Steps to Beach

Waterfront w/ private dock. Renovated upscale home + new hot tub, full city bay views w/summer sunsets+sunrise. Steps to Minet's Point beach & park. 4 proper bdrms & 2 pull out couches(Queen & Twin) 3 full bthrms + sauna, over 2400+sqft. Prking for 3 cars, additnal prking available via lot beside. Gas BBQ, fire pit, 2x gas FP, fast Wifi & 77" TV, wshr/dryr. 48amp EV pwr. Minutes to Marina for Seadoo/boat rentals. Wlking distnce to fine dining/pubs & stores. Kite surf & ice fishing

A modern living area is highlighted by a comfortable blue sofa and a matching armchair. A round coffee table sits in the center, with a decorative plant nearby. Natural light streams through large windows, enhancing the spacious feel of the room.

4.95 out of 5 average rating, 121 reviews

Luxury Home Mins to Lake & Beach

Welcome to Your Modern Retreat minutes away from the Lake and Beach! Experience comfort and style in our newly built, beautifully furnished 3-bedroom house, perfect for families, groups, or business travellers. Located in the heart of Barrie, our home offers a serene escape with all the amenities you need for a memorable stay. 50 m to nearest bus stop 1.5 km to grocery stores and Bayfield Mall 3 km to Downtown 4 km to Centennial Beach and Park 6 km to Johnson's Beach

Superhost

A spacious wooden deck features a glass-top dining table surrounded by six chairs, set under a pergola. A gas barbecue is positioned nearby, with views of the lush greenery beyond the deck.

4.83 out of 5 average rating, 162 reviews

Entire House, Private/Clean 5bdr 6 Beds/Sleeps 12

If you are looking to get away for fun with friends or family, Shopping, or planning a trip, this house is exactly the spot for your Barrie stay! Perfect for a family vacay, a wedding trip or a get to gather with friends. We are 5 minutes from downtown Barrie & top attractions, 10 minutes from shopping malls, and ski resorts of Barrie. Brand new furnishings, professionally cleaned & sanitized after each check-out for added peace of mind. Check our recent reviews.