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Condo vacation rentals in Grey Highlands

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Grey Highlands condo rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Weekly condo rentals

Top guest favorite
An open living area is highlighted by a spacious sectional sofa and a round coffee table. Floor-to-ceiling windows offer views of the marina. A dining table with chairs is positioned nearby, and a stylish kitchen island with a marble countertop completes the space.
Condo in Innisfil
4.98 out of 5 average rating, 47 reviews

Lake/Marina Front, Luxury 2 Storie 1500 Sqft At FH

Superhost
A dining table is set on the balcony, featuring two colorful plates of fresh fruit, alongside glasses of orange juice and water. A small vase holds cheerful flowers. In the background, a lush green landscape stretches out, framed by trees under a blue sky.
Condo in The Blue Mountains
4.86 out of 5 average rating, 14 reviews

Spacious/Steps to Village/2 Balconies 1Mtn-1Golf!

Superhost
An open concept studio loft condo features a kitchenette with essential appliances and a cozy living area, complemented by a sofa adorned with decorative pillows. A staircase leads to the upper sleeping area, showcasing a spacious bed situated beside a bedside lamp. Natural light fills the room.
Condo in The Blue Mountains
4.7 out of 5 average rating, 20 reviews

Mountain Loft Suite with Pool and Hot Tub

Guest favorite
A bright living area features a plush beige sofa, a stylish green accent chair, and a dark coffee table atop a soft area rug. Natural light streams through the multi-paned windows, with cozy curtains partially drawn, while a stone fireplace adds a touch of warmth.
Condo in The Blue Mountains
4.92 out of 5 average rating, 267 reviews

Mountainside Studio Bliss: Walk to Slopes, Hot Tub

Superhost
An inviting open-concept living area features a cozy fireplace, wooden staircase, and a large TV mounted on the wall. Natural light fills the space, highlighting the comfortable seating arrangement and a wooden cabinet filled with DVDs. The ambiance is relaxed and welcoming.
Condo in The Blue Mountains
4.84 out of 5 average rating, 205 reviews

Still Winds - Outdoor Pool / Shuttle to Blue

Guest favorite
An open-concept living area features a large sectional sofa and a coffee table centered on a textured rug. A cozy fireplace is flanked by windows, allowing natural light to fill the space. Decorative wall paddles add a subtle touch of charm.
Condo in The Blue Mountains
4.92 out of 5 average rating, 118 reviews

The Fairway Chalet

Top guest favorite
The living area features a light-colored sofa paired with a stylish armchair, placed on a neutral-toned area rug. Large glass doors provide access to the private patio, allowing natural light to fill the space. An elegant coffee table is centered in the area, complemented by modern decor.
Condo in Innisfil
4.95 out of 5 average rating, 62 reviews

Walkout to Courtyard w/ Pool, Hot Tub and Fire Pit

Top guest favorite
A contemporary living space is highlighted by a light-colored sofa adorned with accent pillows. A wooden coffee table sits at the center, and a modern kitchen with sleek cabinetry and stainless-steel appliances is visible in the background. Natural light flows through the window, enhancing the inviting atmosphere.
Condo in Innisfil
4.98 out of 5 average rating, 63 reviews

Romantic Stay at Friday Harbour Resort Lake Simcoe

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Pet-friendly condo rentals

Guest favorite
A spacious living area features a dark leather sofa complemented by blue accent pillows. A wooden coffee table holds magazines, while a decorative rug covers the floor. The open layout connects to a modern kitchen with white cabinetry, bar seating, and large windows allowing natural light.
Condo in The Blue Mountains
4.92 out of 5 average rating, 155 reviews

Large 3BR Modern Luxury Escape | Walk to Blue

Superhost
A modern kitchen area features blue cabinetry with open shelves displaying neatly arranged dishes. A central island with seating for two is complemented by sleek bar stools. Stainless steel appliances are integrated into the kitchen layout, providing a functional and inviting cooking space.
Condo in The Blue Mountains
4.86 out of 5 average rating, 450 reviews

Base of Blue Mountain, Modern Studio

Guest favorite
A bright studio suite is presented, featuring a spacious bed with neutral bedding. A small dining table with two white chairs is positioned beside a large window, offering views of the cityscape. A television is mounted on a simple stand in the corner.
Condo in Yorkville
4.86 out of 5 average rating, 210 reviews

Stylish Yorkville Studio: Near U of T & ROM

Guest favorite
A wide wooden boardwalk is shown alongside a marina, with modern buildings lining the waterfront. Soft sunlight reflects off the water and the boats docked. Comfortable blue chairs are placed on the green lawn, inviting relaxation while enjoying the serene harbor view.
Condo in Innisfil
4.93 out of 5 average rating, 222 reviews

Designer Condo with beautiful harbour view.

Guest favorite
A modern living area is presented, featuring a pull-out couch draped with a light gray blanket. A glass-top coffee table is centered on a striped rug. Adjacent, a sleek entertainment unit is visible with a large television. Natural light is filtered through sheer curtains.
Condo in Innisfil
4.88 out of 5 average rating, 299 reviews

Resort Condo in Friday Harbour

Guest favorite
A modern kitchen area is equipped with stainless steel appliances, including a large refrigerator and oven. A glass-topped breakfast bar is accompanied by two neutral-colored stools. Decorative wall art and a small plant add visual interest, while natural light enhances the bright ambiance.
Condo in Downtown Toronto
4.92 out of 5 average rating, 246 reviews

Vibrant downtown place

Guest favorite
The exterior showcases a striking building with a red-and-white color scheme, surrounded by lush greenery. An indoor pool area is visible through large glass windows. An inviting fireplace is framed by stone, while a spacious dining area features a wooden table accompanied by six chairs.
Condo in Oro
4.88 out of 5 average rating, 180 reviews

Private 2BR Condo | 4 Beds+Pool+Resort

Guest favorite
A bright living area features a modern fireplace surrounded by decorative plants. A dark wooden coffee table and a light-colored sofa are highlighted in the cozy space. Large windows allow natural light, offering views of the outdoors complemented by artwork on the walls.
Condo in Elora
4.87 out of 5 average rating, 131 reviews

Elora Grandeur: The Pinnacle Retreat"

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Condo rentals with a pool

Guest favorite
An indoor swimming pool glistens under natural light, with large glass windows framing views of vibrant fall foliage. Comfortable lounge seating is arranged nearby, creating a tranquil relaxation area. The pool features clear, inviting water with lane markers visible in the foreground.
Condo in Oro
4.88 out of 5 average rating, 258 reviews

Spacious 1-br w jacuzzi at Horseshoe Valley

Guest favorite
An aerial view reveals a sprawling community of low-rise condos, interspersed with patches of green including a golf course. A swimming pool is visible within the complex, surrounded by a landscaped area. The surrounding hills are dotted with trees, showcasing a range of natural colors.
Condo in The Blue Mountains
4.89 out of 5 average rating, 176 reviews

Close to Village, 2 Bedrooms , Rivergrass

Guest favorite
The kitchen displays modern appliances, including a refrigerator, microwave, and stove, set against a stylish backsplash. A granite countertop extends into a small dining area with two black stools, while light fixtures offer bright illumination in the space.
Condo in The Blue Mountains
4.81 out of 5 average rating, 206 reviews

Blue Mountain Escape, WIFI, Base of North lift

Top guest favorite
An outdoor swimming pool is centered within a landscaped courtyard, surrounded by contemporary apartment buildings. Comfortable lounge chairs line the pool deck, while a graceful pathway leads to the water's edge. Lush greenery frames the area, enhancing the tranquil atmosphere.
Condo in North York
5 out of 5 average rating, 102 reviews

The Penty: Luxurious Penthouse with Pool, Hot Tub

Superhost
Condo in The Blue Mountains
4.84 out of 5 average rating, 92 reviews

Clearview Chalet - Modern 3BR / Outdoor Pool

Superhost
An outdoor swimming pool is surrounded by lounge chairs and umbrellas, set against a backdrop of vibrant greenery and seasonal flowers. The clear blue water reflects the sunny sky, creating a refreshing atmosphere for relaxation and leisure.
Condo in The Blue Mountains
4.91 out of 5 average rating, 120 reviews

The Highlands - Outdoor Pool / Shuttle to Blue

Guest favorite
A modern living area is featured, showcasing a grey sofa and two armchairs. A coffee table sits in front of the seating arrangement, and a wall-mounted television is positioned above a linear fireplace. Natural light streams through large windows, illuminating the space.
Condo in Blue Mountains
4.92 out of 5 average rating, 353 reviews

2 Bedroom, 2 Level Condo on Blue Mountain!

Superhost
Condo in The Blue Mountains
4.79 out of 5 average rating, 193 reviews

Slopeside Sanctuary - Ski In/Ski Out

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Quick stats about condo rentals in Grey Highlands

  • Total rentals

    330 properties

  • Nightly prices starting at

    R350 ZAR before taxes and fees

  • Total number of reviews

    31K reviews

  • Family-friendly rentals

    240 properties are a good fit for families

  • Pet-friendly rentals

    80 properties allow pets

  • Rentals with a pool

    210 properties have a pool

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Grey County
  5. Grey Highlands
  6. Condo rentals