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Condo vacation rentals in Grey Highlands

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Vacation rentals for every style

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Popular amenities for Grey Highlands condo rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Weekly condo rentals

Top guest favorite
A spacious living area features a comfortable couch and coffee table surrounded by decorative plants. Large windows provide ample natural light, framed by light-colored curtains. A stylish chandelier hangs overhead, and a wall-mounted TV offers entertainment options, creating a relaxing and inviting environment.
Condo in Innisfil
5 out of 5 average rating, 67 reviews

Luxury Stay at Friday Harbour Resort Lake Simcoe

An open-concept living area showcases a modern kitchen with stainless steel appliances and a large island. A cozy seating area features a dark sofa and an armchair, positioned near a stone fireplace. Natural light fills the space through multiple windows.
Condo in The Blue Mountains
4.92 out of 5 average rating, 179 reviews

Blue Mountain condo in Historic Snowbridge

Guest favorite
A modern dining area features a large wooden table surrounded by six upholstered chairs. Above, a geometric light fixture provides illumination, while artwork hangs on the wall, complementing the warm tones of the cabinetry visible in the kitchen.
Condo in The Blue Mountains
4.89 out of 5 average rating, 177 reviews

Close to Village, 2 Bedrooms , Rivergrass

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

Top guest favorite
The marina at twilight features calm waters reflecting the vibrant colors of the sunset. Multiple boats are docked along the well-lit marina, with modern buildings lining the shore, creating a serene and inviting atmosphere.
Condo in Innisfil
4.96 out of 5 average rating, 83 reviews

Luxury Getaway @ Friday Harbour Condo at Marina

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, 63 reviews

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

Guest favorite
A welcoming living area features a comfortable gray sofa and two recliners. A coffee table occupies the center, with a potted plant adding a touch of greenery. Warm light is provided by two lamps, and a playful artwork of a dog wearing sunglasses adorns the wall.
Condo in Stayner
4.9 out of 5 average rating, 270 reviews

Sheard's Landing

Superhost
A spacious living area includes a comfortable gray sofa adorned with decorative pillows featuring bear and tree motifs. A dining table for four is visible in the background, along with a well-equipped kitchen that showcases modern appliances and counter seating.
Condo in The Blue Mountains
4.79 out of 5 average rating, 193 reviews

Slopeside Sanctuary - Ski In/Ski Out

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Pet-friendly condo rentals

Guest favorite
A modern living area is showcased, featuring a spacious lounge with a stylish sectional couch, accent chairs, and a flat-screen TV. A dining table with white chairs is positioned alongside a sleek kitchen island, illuminated by pendant lights, with natural light coming through large windows.
Condo in Barrie
4.93 out of 5 average rating, 136 reviews

Bright MCM 2 Bedroom Walk Up with Private Deck/BBQ

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
4.87 out of 5 average rating, 15 reviews

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

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 cozy sleeping area features a wooden bed frame with a plush white comforter. A portrait of a Highland cow is displayed above the headboard. Adjacent mirrors and wooden furniture provide storage, while floral decorations frame the image.
Condo in The Blue Mountains
4.89 out of 5 average rating, 462 reviews

Summer Splendor at Blue Mountain

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 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, 223 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, 301 reviews

Resort Condo in Friday Harbour

Superhost
The living room features a cozy sectional sofa against a light blue wall, complemented by a textured brick feature wall. A flat-screen TV is positioned on a modern media console, while a wood coffee table adds warmth to the space, providing a relaxed environment.
Condo in Collingwood
4.77 out of 5 average rating, 142 reviews

Collingwood Boutique Suites - Unit B

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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, 259 reviews

Spacious 1-br w jacuzzi at Horseshoe Valley

Guest favorite
An outdoor swimming pool is surrounded by a wooden deck and clear blue skies. The calm water reflects the greenery from nearby trees. A shaded area with colorful umbrellas provides seating for relaxation, while a fence ensures privacy and safety around the pool area.
Condo in The Blue Mountains
4.81 out of 5 average rating, 201 reviews

Mountainside Escape at Blue - Outdoor Pool

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

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

Superhost
Condo in The Blue Mountains
4.81 out of 5 average rating, 95 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, 122 reviews

The Highlands - Outdoor Pool / Shuttle to Blue

Guest favorite
A spacious courtyard features a tranquil pool surrounded by modern condominium buildings. Lush greenery enhances the area, while lounge chairs are positioned near the water. Bright blue skies and natural light create a cheerful atmosphere, ideal for relaxation and leisure activities.
Condo in Innisfil
4.88 out of 5 average rating, 156 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

Top guest favorite
Condo in Shanty Bay
4.98 out of 5 average rating, 49 reviews

Wildwood HotTub+Indoor/Outdoor Pool+Sauna+GameRoom

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Quick stats about condo rentals in Grey Highlands

  • Total rentals

    330 properties

  • Nightly prices starting at

    ﺩ.ﺇ73 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