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Condo vacation rentals in Grey Highlands

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Top-rated condo rentals in Grey Highlands

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Top guest favorite

A balcony is presented with a wooden table and four chairs, accompanied by a patio heater. Potted plants and decorative greenery are arranged along the railing, enhancing the outdoor space. Soft lighting and a view of nearby buildings create a calm, inviting environment.

Condo in Innisfil

4.97 out of 5 average rating, 165 reviews

Stylish getaway condo, resort living

Modern, bright, luxurious, fully furnished 2 bedroom condo with balcony overlooking beautiful courtyard, harbour and lake views of Friday Harbour All Seasons Resort. Features activities, golf course, nature preserve & trails, waterfront beach, boating, canoeing, biking & more. King bed, Queen bed, sleeps 4. Smart TV, High Speed WiFi. 1 reserved parking spot and paid per night lot parking, BBQ, In-Suite Laundry NOTE: short stay of 2-3 nights must book full weekends and not break up weekend dates

A modern living area features a comfortable gray sofa arranged around a glass-topped coffee table. A large TV is positioned on a white media console. Natural light fills the space through floor-to-ceiling windows, complemented by stylish decor and a contemporary lighting fixture.

Condo in Innisfil

4.84 out of 5 average rating, 180 reviews

Marina view at Friday Harbour 2bd/2bth Pool option

This Black Cherry model condo is the most sought after layout at Friday harbour, featuring a spacious-well-designed kitchen, living room and balcony area with two bedrooms and two bathrooms ideal for families, couples, or solo travellers. Enjoy comfortable sleeping with a king bed in the master bedroom also featuring an ensuite bath and walking closet, and a Queen bed in the second bedroom. Enjoy a view of the beautiful landscaped courtyard out to the marina, while lounging or eating outside.

A modern pool area is surrounded by lush greenery and contemporary buildings. Lounge chairs are positioned around the pool, providing relaxation spots. A covered area features seating, while guests enjoy the serene environment. The atmosphere reflects a stylish and inviting outdoor space.

Condo in Innisfil

4.94 out of 5 average rating, 115 reviews

Friday Harbour Luxury Condo Escape, Sleeps 4

Escape and unwind in our luxurious, open concept fully furnished 1 bedroom condo with a walkout balcony located in Friday Harbour All Seasons Resort community. Enjoy the season with access to golf, walking trails, beach, boating, biking, live music, events and weekend markets on the boardwalk. Queen bed + pullout, sleeps 4. Two Smart TVs, High Speed WiFi. Relax on furnished balcony overlooking our private pool, courtyard & beautiful sunset. 1 Free Parking, Electric BBQ, In-Suite Laundry

An aerial view captures a modern marina building named 'Harbour Master' facing the calm waters of Lake Simcoe. Surrounding structures are visible along the shoreline, with boats moored at the docks and greenery framing the tranquil scene at dawn.

Condo in Innisfil

4.85 out of 5 average rating, 112 reviews

2 Bedroom Condo at Friday Harbour Resort

Luxury 2 bedroom 2 bathroom condo at the gorgeous Friday Harbour Resort on Lake Simcoe. Fully furnished and includes everything you need for a comfortable stay, including fully equipped kitchen, linens, bedding, towels, shampoo and conditioner, laundry, toilet paper, utensils, pots and pans, dishes, etc. Quiet building on the 2nd floor with a main view of the terrace gardens and slight view of the marina. Please visit the Friday Harbour website for information about the resort and amenities.

A spacious bedroom features a king-size bed dressed in neutral linens, flanked by two bedside tables. Large windows provide natural light and overlook greenery. A comfortable armchair sits in the corner, with a light wooden dresser nearby, accentuated by warm-toned flooring.

Condo in The Blue Mountains

4.98 out of 5 average rating, 151 reviews

Lovely 3 Bedroom Condo with Stunning View and Pool

Beautifully Newly Renovated Condo Located in Rivergrass on Fairway Crt, which is in the heart of Blue Mountain and Steps to the Village! Condo features 3 bedrooms(One king, two Queen and Two Twin beds with trundle pullouts), 2 full baths, kitchen, washer/dryer, living room, and dining room. Outdoor Pool (Middle of June and closes Sept 3) and Hot Tub(All Year). Short walk or take the shuttle bus to the village. Our cleaners are extensively disinfecting and sanitizing between each booking.

Condo in Innisfil

4.88 out of 5 average rating, 207 reviews

Lake Simco penthouse at Friday Harbour resort

Modern Penthouse with beautiful furniture located in the Friday Harbor Resort with beautiful patio…outside pool in the summer and hot tub year round ..gas barbecues ..seating and dining area with fire place large balcony where smoking is allowed. Beautiful sunset on the right Forest 200acres with beautiful trails Beach area with rental equipment .paddle board .basketball court ..bike rentals… eagle nest golf with the restaurant overlooking golf course Beach club restaurant on the water

A modern condominium complex features multiple connecting buildings with large windows and balconies. A landscaped courtyard is visible, showcasing stone pathways, patio furniture, and greenery. The outdoor seating areas provide space for relaxation amid the well-maintained surroundings.

Condo in Innisfil

4.89 out of 5 average rating, 140 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

Experience the allure of Friday Harbour! Stay in this gorgeously furnished 1-bedroom condo, complete with a pullout sofa bed. Enjoy the stunning outdoor relaxation area that overlooks the courtyard pool. The condo features a spacious bedroom with a closet and a large bathroom. Its layout is perfect for both relaxation and entertainment, with an open concept living area and a kitchen featuring an island. Embrace the ultimate indoor and outdoor living experience at Friday Harbour!

A landscaped area is visible with neatly arranged greenery and paths leading to the building's entrance. Modern balconies overlook the courtyard, while trees provide a touch of nature. Paving stones create structured walkways within the outdoor space, inviting exploration.

Condo in Innisfil

4.88 out of 5 average rating, 278 reviews

Resort Condo in Friday Harbour

Exquisite 1 Bedroom condo with separate pull out couch. Get ready to relax and unwind. Only 45 minutes from Toronto. Great getaway for couples, singles, work travelers and those just wanting to relax or some adventure. Enjoy the marina, boardwalk, shops, restaurants, nature trails, golf course and much more. Visit: friday harbour .com for complete list of activities and explore all that FH has to offer. Owner only restrictions apply.

Condo in The Blue Mountains

4.86 out of 5 average rating, 245 reviews

Stylish & Spacious 2 Bdrm/2 bths/2 balc Condo Loft

Welcome to our Stylish and Spacious 2 bedroom, 2 bathroom, 2 balcony & 2 level condo loft. Located at the foot of the north hills at Blue Mountain with ski-to-slope access and stunning views of the hills and just a short walk away to Blue Mountain Village. It will comfortably sleep 4, with room for 6 with 1 sofa bed. Linens, towels and toiletries are available as well as unlimited wifi. Complimentary parking is available.

A wide promenade is lined with modern buildings that host various shops and restaurants. Planters with greenery are positioned along the pathway, and people are seen walking, some pushing strollers. Flags flutter in the breeze, enhancing the inviting outdoor atmosphere.

Condo in Innisfil

4.82 out of 5 average rating, 473 reviews

Lovely 2-bedroom at Friday Harbour

Friday Harbour Resort welcomes you to the start of something extraordinary. Friday Harbour was designed to be a destination. A destination you look forward to visiting all year round, where you can unwind and truly feel relaxed. Whether you arrive 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 way to enjoy your days.

A modern balcony is equipped with gray outdoor seating, featuring a low table. Glass panels provide a clear view of the surrounding area. Lush green plants are positioned in one corner, enhancing the outdoor space's appeal.

Condo in Innisfil

4.95 out of 5 average rating, 146 reviews

Lake Simcoe Resort Retreat

Beautiful, fully furnished one bedroom vacation retreat in the vibrant resort community of Friday Harbour. Experience the all-season recreation including the beach, marina, nature preserve, eighteen hole golf course, sports facilities and more! Find everything you're looking for, from grocery stores and restaurants to coffee shops and the LCBO, just steps from the boardwalk.

A spacious outdoor patio features modern furnishings, including a large sectional sofa and a central coffee table. Ample seating is provided by numerous dining tables and chairs arranged under overhead lighting, with a backdrop of large glass doors leading to the interior space.

Condo in Innisfil

4.87 out of 5 average rating, 223 reviews

2BR Getaway at Friday Harbour All Season Resort

2 Bedroom Condo at Friday Harbour Resort on Lake Simcoe. 45 mins from Toronto, 15 mins from Go Station. Great getaway for couples, families or those just wanting some time to relax and unwind. Visit the marina, take a walk on the boardwalk or spend the day at the beach, spend the afternoon walking the serene nature preserve trails, golf course and much, much more....

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Grey Highlands condo rentals

Free parking on premises

Air conditioning

Weekly condo rentals

Condo in The Blue Mountains

4.88 out of 5 average rating, 123 reviews

Blue Mountain Getaway at North Creek Resort

An elegant dining space features high ceilings supported by wooden beams. Multiple tables are arranged throughout, with soft lighting fixtures adding to the ambiance. A bar area can be seen in the background, enhancing the inviting atmosphere for guests.

Condo in Innisfil

4.96 out of 5 average rating, 50 reviews

Your Dream Escape at Friday Harbour - 2Bdrm 2Bath

Condo in Innisfil

4.9 out of 5 average rating, 202 reviews

Beautifully Furnished New Condo at Friday Harbour

Lush greenery surrounds a pathway leading to a tennis court, with a view of the hillside visible in the background. The scene is framed by tall trees, creating a natural ambiance and connecting guests to the outdoor environment.

Condo in The Blue Mountains

4.79 out of 5 average rating, 218 reviews

Mountainside Retreat - Ski in/out - Endless Coffee

A spacious balcony is captured with modern outdoor furniture, including a table and chairs. Large glass panels provide an unobstructed view of the surrounding buildings and the clear blue sky. The balcony flooring is made of sleek, grey tiles.

Condo in Innisfil

5 out of 5 average rating, 8 reviews

Resort Living with Amazing Water Views, Balcony

A shared outdoor pool area features a circular pool surrounded by lounge chairs and blue umbrellas. Wooden decking encircles the space, while lush greenery provides a natural backdrop. The scene is tranquil, ideal for relaxation during the summer months.

Condo in Blue Mountains

4.83 out of 5 average rating, 270 reviews

Private Backyard/Shuttle/Pool/10min walk 2 village

A covered patio area features two black chairs with striped cushions. A wooden railing surrounds the space, offering an unobstructed view of the nearby tennis courts and parking area. Stairs leading to the upper level can be seen in the background.

Condo in The Blue Mountains

4.85 out of 5 average rating, 399 reviews

Mountain Side One Bedroom

A snowy landscape reveals a vibrant village scene with multi-colored buildings, many featuring balconies. A ski hill rises in the background, blanketed in fresh snow, while evergreen trees add a touch of greenery to the winter setting.

Condo in The Blue Mountains

4.97 out of 5 average rating, 152 reviews

Rustic Chic Renovated 2Bd Condo by Village

Pet-friendly condo rentals

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

4.94 out of 5 average rating, 125 reviews

Bright MCM 2 Bedroom Walk Up with Private Deck/BBQ

A modern living area showcases a plush sofa with red and neutral accents. A wooden coffee table sits in the center, complemented by a vibrant piece of wall art. The open layout connects to the dining area and kitchen, enhancing the spacious feel.

Condo in Davisville Village

4.87 out of 5 average rating, 30 reviews

Modern Luxury condo 2B+2B at Yonge and Eglinton

A spacious living area features a light-colored sectional sofa with decorative pillows. A mirrored wall reflects natural light, enhancing the ambiance. A dining area is visible in the background, with a round table surrounded by stylish chairs. Windows allow for bright illumination.

Condo in North York

4.84 out of 5 average rating, 82 reviews

Lovely Toronto entire Condo!Renovated!Amazing view

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

4.9 out of 5 average rating, 439 reviews

Spring Sneak Away | Blue Mountain

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, 440 reviews

Base of Blue Mountain, Modern Studio

A stylish living room is depicted, featuring a plush gray sofa and two comfortable armchairs. A wooden coffee table centers the space. A large mirror reflects the natural light coming through expansive sliding glass doors that open to a patio area. Warm tones from a nearby lamp enhance the inviting ambiance.

Condo in Innisfil

4.81 out of 5 average rating, 32 reviews

Convenient Garden Walkout to Pier, 2BR+2bath Condo

A spacious seating area is presented with a sleek black sofa and a light gray Klik Klack sofa, complemented by a dark blanket draped over the seat. Sunlight filters through shuttered windows, illuminating the area. A brown storage ottoman is positioned between the couches.

Condo in The Blue Mountains

4.76 out of 5 average rating, 753 reviews

Mountainside Studio w/Kitchen - Beside Blue

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

4.78 out of 5 average rating, 134 reviews

Collingwood Boutique Suites - Unit B

Condo rentals with a pool

An aerial view captures a modern courtyard featuring a private outdoor pool, surrounded by sleek buildings. Lounge chairs are positioned along the pool's edge, and landscaped areas with greenery add to the serene atmosphere. Soft light from the evening sky complements the setting.

Condo in Innisfil

5 out of 5 average rating, 62 reviews

FH Aquarius Bldg: Modern 2BR/2B Condo

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, 163 reviews

Close to Village, 2 Bedrooms , Rivergrass

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

4.91 out of 5 average rating, 111 reviews

The Fairway Chalet

The exterior of the condo features a modern architectural design with a sheltered entrance. Stone columns support the upper balcony, and a set of stairs leads up to the main door. Soft lighting illuminates the entrance, enhancing the overall appearance.

4.81 out of 5 average rating, 31 reviews

Large 1 Bedroom Condo Near Horseshoe

A modern two-story townhouse complex is presented, featuring balconies with comfortable seating. Above the outdoor pool, laundry items are displayed on a clothesline. A well-maintained grassy area surrounds the pool, providing a relaxing atmosphere for guests.

Condo in Wasaga Beach

4.91 out of 5 average rating, 79 reviews

Wasaga Beach/WaterFront BeachHouse/ BBQ/AC/parking

An open living area features a deep green sofa, a round coffee table, and a warm rug on light wood flooring. Natural light floods through large glass doors adorned with teal curtains, framed by plants and decorative wall art, creating a cozy and vibrant atmosphere.

Condo in Innisfil

4.98 out of 5 average rating, 47 reviews

Bohemian Luxury at Friday Harbour Resort Simcoe

Top guest favorite

The indoor saltwater pool area features large windows allowing for natural light to flood the space. The pool is bordered by tile flooring with safety signage visible. Minimalistic design elements include sleek lines and modern lighting, creating a contemporary swimming environment.

Condo in Davisville Village

4.93 out of 5 average rating, 265 reviews

SpectacularPenthouse VIEWS/ POOL /free Parking

An outdoor pool area is featured, surrounded by lounge chairs and picnic tables. A large building with expansive glass windows serves as a backdrop, while bright blue umbrellas provide shade. The surrounding greenery enhances the tranquil ambiance of the resort.

4.87 out of 5 average rating, 89 reviews

Hillside Haven: Serene Studio Retreat for 4

Quick stats about condo rentals in Grey Highlands

Total rentals
310 properties
Nightly prices starting at
$20 before taxes and fees
Total number of reviews
30K reviews
Family-friendly rentals
230 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with a pool
200 properties have a pool

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