Ski-in/Ski-out holiday rentals in Innisfil

4.86 out of 5 average rating, 138 reviews

An A-frame house featuring a white exterior and a steep roof stands beside a serene lake. A gravel driveway leads to the entrance, surrounded by greenery. Large windows allow ample natural light, providing views of the lake and trees in the background.

Home in Little Lake

Lakefront detached house on the little lake

♥️an unique, lovely elf house in front of the little lake. Here you’ll find a unique hideaway in the middle of the city Barrie with gorgeous lake views as far as the eye can see. ♥️ Only one hour drive from Toronto. Walking distance to everywhere (shoppers,restaurants, cinemas….) ♥️This home including new furniture, microwave, coffee maker, washing machine and all other appliances ! Walk out the back door and be greeted by our updated dock where you can fish for pike, perch, pickerel and bass.

A spacious room features a king-size bed adorned with a leaf-patterned duvet. A comfortable seating area includes a sofa, a wooden coffee table, and a dining table with four chairs, while large windows invite natural light.

4.86 out of 5 average rating, 84 reviews

Country Retreat Horseshoe Valley

Experience country living in this serene condo, offering an ideal escape from the hustle of the city. Recently renovated, it promises to impress. Savor your morning coffee on your private balcony, take a dip in the indoor/outdoor pool, or enjoy a cocktail by the outdoor gas fire pit. King-size bed and a queen pull-out, this room is perfect for couples, families, or friends. Steps from Horseshoe Ski Resort, Treetop Trekking, Vetta Spa, Hiking Trails, and Mountain biking- something for everyone!

4.99 out of 5 average rating, 114 reviews

An open concept living area features rustic wood beams and sliding barn doors. Comfortable wicker chairs are paired with a wooden coffee table, while a cozy sofa adds to the inviting space. The modern kitchen is visible in the background, creating a seamless flow.

Guest house in Mansfield

Brookside Cottage - Charming Rural Getaway Mulmur

Our cozy guest house, situated in the Headwaters region, has it all! Close to hiking,golfing,biking,skiing. XCski/snowshoe from your door! Big skies for astronomers and astrophotography! We offer 32 acres of forest and fields for walking and taking in the magnificent views. The area boasts fine restaurants, boutiques, markets and artisans. Minutes to Mono Cliffs, Boyne, Mansfield Ski Club and easy driving to Blue Mountain and Wasaga Beach. Ideal for couples, solo adventurers or a small family.

4.91 out of 5 average rating, 98 reviews

An aerial view captures the expansive layout of Friday Harbour, showcasing various buildings along the marina and natural surroundings. A peaceful golf course is visible with a distinctive lighthouse, all framed by serene water reflections under a twilight sky.

Apartment in Innisfil

Family-friendly luxury getaway at Friday Harbour

Happy Holidays! At Canada's most sought after all seasons resort, you, your family, and friends can unwind to the peaceful serenity of Lake Simcoe, spend hours in the 200-acre Nature Preserve, experience unforgettable fine dining, or stroll along the beautiful boardwalk. Our one-of-kind 2-bedroom open concept luxury Corner unit with floor-to-ceiling windows will give you a taste of paradise - an hour away from the Greater Toronto Area! Come and enjoy all that Friday Harbour has to offer!

5 out of 5 average rating, 14 reviews

A welcoming living area is highlighted by comfortable seating arrangements, including a sofa and two armchairs. A round coffee table sits in the center, surrounded by a soft area rug. A mounted television is above a modern fireplace, with natural light filtering through the windows.

Home in Barrie

Luxurious and Beautiful, Barrie

Welcome to our cozy retreat in Barrie, Ontario, just a short walk from the beautiful waterfront and popular beaches. Our home is perfect for a relaxing getaway or an adventurous weekend, offering modern amenities, a fully equipped kitchen, and a spacious outdoor patio in a quiet, family-friendly neighborhood. Our retreat offers year-round appeal, with activities like beach days in summer and skiing in winter. With free parking and easy access, we’re excited to host your unforgettable stay!

4.85 out of 5 average rating, 27 reviews

Home in Angus

The Angus Nest

Enjoy this bright and open space that features a master suite with a jacuzzi, cozy family room with a fireplace, and a fully equipped kitchen with modern appliances, and laundry room. Stay entertained with high-speed internet and a smart TV, and take advantage of the spacious deck. Four parking spots available extra spot if needed. Whether you're planning a family vacation, a ski trip, or a peaceful retreat, our home is the perfect place to relax and unwind. Book your stay today!

4.86 out of 5 average rating, 113 reviews

A bright and spacious living area features a comfortable white sofa paired with dark blue accent chairs. A stylish dining table is set for meals, while a gas fireplace and mounted television create a cozy atmosphere. Natural light fills the room through large windows.

Home in Horseshoe Valley

King Bed, Pool, Gym, Ravine View, Your Getaway!

Enjoy a stylish experience in this spacious and serene space at Highland Estates Resort. You get a completely equipped designer suite that is perfect for couples sneaking away, or families looking for the perfect vacation. Enjoy a peaceful night in your private Jacuzzi then snuggle up in a King Bed. The next day, prepare your own meal in the fully equipped kitchen with Microwave and Electric Stove. Access Netflix, Prime, Disney+. Get Some Fun in the Sun and Book Today

4.94 out of 5 average rating, 90 reviews

Apartment in Innisfil

Luxury Getaway | Friday Harbour Condo

Book your accommodations with us & enjoy the prestigious FH Resort. FH wasn’t designed to be a place. It was designed to be a destination. Were you can unwind, disconnect & reconnect all your senses with the healing powers of the forest & beautiful sunsets, truly feel relaxed. Whether you come to take in the peaceful serenity of the lake, spend hours in the Nature Preserve or mingle with friends over a gourmet meal, there’s no shortage of ways to enjoy your days."

5 out of 5 average rating, 17 reviews

The exterior of a spacious cottage is displayed, surrounded by lush green grass and trees. Large windows provide ample natural light to the interior, while a stone pathway leads to the entrance. The multi-level structure features a red roof and earthy stone accents.

Cottage in Utopia

Simcoe Cottage + Hot Tub + Sauna + Private Retreat

Welcome to your own private cottage situated on 3 acres of beautiful woodlands, where comfort and relaxation awaits! This massive custom-built cottage is the perfect setting for large families or travelling friends. Our tastefully furnished oasis boasts one of a kind décor, with plenty of room for indoor and outdoor activities. All accompanied with private access to the Nottawasaga River. Only 1hr from Greater Toronto Area.

4.93 out of 5 average rating, 191 reviews

A cozy living area features an orange L-shaped sofa adorned with decorative pillows, paired with a round coffee table. A 55" smart TV sits on a sleek black stand against the wall, surrounded by neutral decor and natural light from the nearby window.

Home in Barrie

4 Bedroom Fully Private Townhouse in Barrie

This spacious four-bedroom, four-bath townhouse is in Barrie South. It is a fully private and independent house, so you will have full privacy in and out. Enjoy the beautiful lake, which is five minutes away. Guests will have access to a fully stocked kitchen, washer/dryer, free high-speed internet (1500mbps), and a 55" smart TV with popular streaming services. All popular stores and amenities are nearby, within five minutes.

The bedroom displays a king-sized bed adorned with soft linens and multiple decorative pillows. Next to the bed, a stylish lamp provides warm light, while three framed nature photos hang above the headboard. A cozy seating area features a plush sofa with decorative cushions and a small table, enhancing comfort.

4.98 out of 5 average rating, 50 reviews

Serenity 1Bed+Sauna+HotTub+Indoor/OutdoorPool

Welcome to our modern zen retreat in Horseshoe Valley—perfect for families or friends looking to relax, explore, and make lasting memories. Just 2 hours from Toronto, our condo offers a prime location to experience it all. Minutes away from the Vettä Nordic spa, skiing, mountain biking, golf, tree-top trekking and more. Created with tranquility in mind, our space is the perfect place to return to after a day of adventure.

Cottage in Victoria Harbour

A year-round Jacuzzi hot tub sits near the edge of the property, featuring a smooth surface and built-in jets. In the background, a fire pit is surrounded by blue Adirondack chairs, with kayaks lined up on the grass and the expansive waterfront visible.

4.85 out of 5 average rating, 62 reviews

Perfect summer gateway.lots to do here

Discover your perfect summer escape at our fully renovated, private lakefront cottage on Georgian Bay in Victoria Harbour, less than 2 hours from the GTA. Enjoy breathtaking sunrise views, a cozy fire pit, BBQ, and a fun-filled game room with a pool table. Relax year-round in the hot tub under the stars. LCBO and Foodland are just 5 minutes away, and outdoor activities like biking and kayaking are right at your doorstep

Popular amenities for Innisfil ski-in/out rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Ski-in/out house rentals

A bright bedroom features a spacious bed with blue linens and a modern ceiling fan. A desk is positioned nearby, while large sliding glass doors open to a view of the backyard, allowing natural light to enter the room.

Private room in Barrie

4.6 out of 5 average rating, 10 reviews

Bright room! Free parking

A spacious outdoor deck provides a comfortable lounge area, featuring a sectional sofa, colorful accent chairs, and a dining table. A large yellow umbrella offers shade, while views of the private dock and calm waters create a serene setting for relaxation.

Home in Innisfil

4.74 out of 5 average rating, 72 reviews

Luxurious Lake front Island Townhome, Innisfil, ON

A cozy bedroom features a spacious bed with striped bedding and a light-colored headboard. A small desk and chair are positioned beside the window, which lets in natural light. A piece of wall art adds a splash of color, complementing the soft, neutral tones.

Private room in Barrie

lovely room!

Private room in Toronto

New place to stay

Spacious and Bright Ground unit near Yonge-Finch

Three snowmobiles are seen traveling along a snow-covered trail surrounded by tall, bare trees. The path is flanked by dense foliage, creating a natural corridor. Snow is kicked up from the tracks, highlighting the winter recreational activity.

Home in Shanty Bay

Nature Lovers Paradise

A comfortable living room features a light-colored sectional sofa with a decorative pillow. Natural light filters through the window, which is covered with sleek shades. French doors are visible, leading to another space, and a framed artwork is positioned on the floor.

Home in Wasaga Beach

Peaceful house at the Beach

The kitchen features modern white cabinetry and sleek stainless steel appliances, including a refrigerator, stove, and dishwasher. Ample counter space is provided, and large windows allow natural light to brighten the area. A neutral tile floor complements the contemporary design.

Home in Innisfil

Cozy bungalow on Yonge st

4.9 out of 5 average rating, 30 reviews

An aerial view of Olive & Willow Lodge reveals a spacious green lawn surrounded by trees. The white house is centrally located, with a driveway leading to the entrance. Scenic highways are visible along the property's edge, enhancing the natural tranquility of the setting.

Home in Uxbridge

Private & Serene 10-Acre Willow Retreat

Family-friendly, ski-in/out home rentals

A spacious studio room features a king-size bed adorned with pillows and a cozy blanket. The kitchenette is equipped with wood cabinetry and essential appliances. A dining area with a round table sits near a window, with a comfortable sofa nestled in the corner.

Flat in Horseshoe Valley

4.67 out of 5 average rating, 3 reviews

Relaxing condo in Shanty Bay Oro

Flat in Barrie

Stylish Downtown Barrie Condo

Guest suite in Toronto

4.8 out of 5 average rating, 56 reviews

New bright lower unit apartment

Flat in Innisfil

Luxury 2 BR/2Bth@ Friday Harbour

4.7 out of 5 average rating, 128 reviews

A modern bathroom is equipped with a walk-in shower featuring marble-like tiles. A wall-mounted mirror reflects soft light from three globe fixtures above a large sink, complemented by grey cabinetry. Two neatly hung towels are visible, and a small rug adds warmth to the floor.

Home in Brampton

Brand new One Bedroom apartment

4.95 out of 5 average rating, 142 reviews

Home in Collingwood

Driftwood on 6th Heritage Downtown Collingwood

Home in Ajax

4.25 out of 5 average rating, 4 reviews

Prestige Accommodation

Flat in Innisfil

Luxury Sunseeker Stay -New 1BR at Friday Harbour

Ski-in/out apartment rentals

5 out of 5 average rating, 18 reviews

Serenity 2Bed+Sauna+HotTub+Indoor/OutdoorPool

A cozy bedroom is presented with a spacious bed adorned in crisp white linens and a dark throw blanket. Flanking the bed are two bedside lamps, adding soft illumination. A plant adds a touch of greenery, while a living area is visible through an open doorway.

5 out of 5 average rating, 18 reviews

NEW Ski-In Ski-Out 1-BED Condo - Pool, Gym, Sauna

The living area is furnished with a light sofa and an accent chair, accompanied by a circular coffee table on a patterned rug. Large windows provide natural light and views of the outdoors. A modern kitchenette showcases sleek cabinetry and an island with seating.

Apartment in Innisfil

4.49 out of 5 average rating, 78 reviews

Romantic stay at Friday Harbour

A spacious studio features a king-size bed with premium bedding, adjacent to a stylish sectional couch. Natural light pours in through large windows, illuminating the open floor plan. A dining table is positioned nearby, providing a comfortable area for meals.

4.69 out of 5 average rating, 74 reviews

Lux Studio in Horseshoe Valley

A cozy bedroom is highlighted by a plush bed adorned with soft linens and decorative pillows. A bedside lamp casts a warm glow, while art prints with nature motifs hang above the bed. Nearby, a modern dresser and a comfortable sofa are visible, providing inviting spaces for relaxation.

4.94 out of 5 average rating, 34 reviews

Serenity Studio Sauna+HotTub+Indoor/OutdoorPool

A two-story building features a red and white facade, with covered balconies and white railings. A path leads toward the entrance, flanked by grass. The exterior is illuminated, ensuring visibility at dusk.

Private room in Horseshoe Valley

4.58 out of 5 average rating, 12 reviews

Margarita Vacation Getaway 2

An open-concept living area features a cozy gas fireplace surrounded by stone, offering a relaxed seating arrangement. A large TV is mounted above the fireplace. The space transitions to a dining area with modern fixtures, while soft natural light filters in through windows.

4.32 out of 5 average rating, 31 reviews

Jacuzzi Suite Relaxing Retreat

An open-concept living area is showcased featuring a cozy gas fireplace framed by a stone wall. A large TV is mounted above it. A dining table with several wooden chairs is visible, alongside a comfortable armchair and coffee table.