Condo vacation rentals in Simcoe County

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Top-rated condo rentals in Simcoe County

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Guest favorite

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.

Guest favorite

A modern, multi-story building is presented, featuring large windows and a distinctive architectural design. Lush green landscaping surrounds the structure, complemented by neatly trimmed bushes and various plants. A patio area is indicated, adding to the property's inviting outdoor space.

Condo in Barrie

4.94 out of 5 average rating, 130 reviews

Bright MCM 2 Bedroom Walk Up with Private Deck/BBQ

Your family will be close to everything when you stay with us. Suite is close to RVH hospital (3.5 km) a walk to downtown Barrie restaurants, shopping, craft brewery and amazing waterfront/ beach. 2 min. to Hwy 400 - Central to local ski resorts (Horseshoe Resort, Mount St. Louis Moonstone, Snow Valley) and golf courses. Newly updated with midcentury modern vibe, kitchen is fully equipped with soapstone counter, undermount sink, dishwasher and fridge with ice-maker. Private outdoor space/BBQ

Guest favorite

The vibrant marina area features a mix of modern buildings with a variety of shops and dining options. People are seen enjoying the outdoor spaces, some walking along paved paths while others gather at shaded seating areas. The water is visible in the background, adding to the lively atmosphere.

Condo in Innisfil

4.93 out of 5 average rating, 115 reviews

Exceptional 2+1 ground floor condo @Friday Harbour

Enjoy early check in and extra late check out in an exceptional 2+1 condo on the ground floor of the desired Aquarius building at Friday Harbour resort. Professionally designed for comfort and style. Aquarius building offers an outdoor pool, BBQ and sitting area. Friday Harbour is an all-season resort, 1 hour north of Toronto, that offers fine dining, LCBO, Starbucks and grocery store within walking distance. Enjoy seasonal activities & events all year round, water sports, live music & more!

Top guest favorite

Condo in Innisfil

5 out of 5 average rating, 144 reviews

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh, unwind and rejuvenate in your very own spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! We know you will enjoy your stay and love the outdoor elements AND the indoor ones too!

Guest favorite

A living area features a comfortable gray sectional sofa adorned with patterned cushions. A wooden coffee table sits in front, with a view of the mountains visible through large windows, framed by light curtains. Natural light brightens the space.

Condo in The Blue Mountains

4.95 out of 5 average rating, 874 reviews

Stunning Mountain Views- WalkTo Blue, Pool, HotTub

SHUTTLE, HOT TUB, SEASONAL POOL! 5-7 minute walk to the Blue Mountain Village. This cozy 2 bedroom condo gives you immediate access to the action or a quiet place to relax by the fireplace while looking out at the mountain views. ★ Enhanced Cleaning Protocol ★ SMART TVs in living room (WIFI and Cable) and bedrooms (WIFI) ★ Family Ready! Games, booster seat, packnplay etc ★ Resort hot tub with indoor changeroom and washrooms Pool opening date June 1st, 2025! Hot Tub open all year round!

Guest favorite

Condo in Innisfil

4.94 out of 5 average rating, 167 reviews

The Friday Flat | Sunny Escape by the Marina

Enjoy access to all of Friday Harbour's world-class amenities, including a golf course and sandy beach. Take a dip in the outdoor pool and explore the kilometres of scenic walking trails that wind through the Nature Preserve Located just a short drive from Toronto, Friday Harbour offers the perfect escape from city life. Spend your days exploring the shops and restaurants of the promenade, or venture out onto the lake Come experience the ultimate waterfront getaway at Friday Harbour

Guest favorite

A modern kitchen is displayed with sleek cabinetry and stainless steel appliances. A granite countertop features a sink and a small potted plant, while a microwave and coffee maker are positioned on the counter. The space is well-lit, providing a clean and uncluttered environment.

Condo in Innisfil

4.89 out of 5 average rating, 143 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!

Guest favorite

A scenic view of a marina area, featuring modern buildings with retail spaces on the ground level. The waterfront shows a series of boat slips, while lounge chairs are positioned along the promenade. Calm waters reflect the surrounding architecture under a soft morning light.

Condo in Innisfil

4.89 out of 5 average rating, 210 reviews

Beautifully Furnished New Condo at Friday Harbour

Whether you’re a nature lover, a romantic seeking the ultimate escape or simply fancy a break from the daily grind, Friday Harbour is the perfect destination only 45 minutes from the GTA. Our 1 bedroom condo has high 9' ceilings, beautiful finishes and everything you need for your getaway. Located on the ground floor, easy access to the boardwalk and local shops. This four seasons resort is designed to entertain everyone. Please note our unit is for adults only.

Superhost

A fire pit surrounded by several Adirondack-style chairs is set on a stone patio, inviting relaxation. Lush green trees and a walking path can be seen in the background, along with a building featuring a red exterior and white accents.

Condo in Oro

4.76 out of 5 average rating, 268 reviews

Cozy Deluxe Studio at Horseshoe Valley

Welcome to Horseshoe Valley, just 1.5 hrs north of Greater Toronto Area. It's a four-season wonder of nature with limitless access to lakes, rivers, trails, and rolling hills. Whether you aim to ski in snow-laden forests of pine, hit golf at one of eighteen golf courses, mountain bike or hike in several landscape trails, soak in the healing experience of Vetta Nordic spa, or simply relax at the tranquility of the area, this place is simply yours to enjoy!

Guest favorite

A circle of blue Adirondack chairs surrounds a fire pit on a sandy area by the water. The lake is visible in the background, with greenery lining the shore under a partly cloudy sky.

Condo in Innisfil

4.88 out of 5 average rating, 281 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.

Top guest favorite

The Lake Club building features a modern architectural design with a large wooden sign displaying 'LAKE CLUB.' The structure is characterized by slanted roofs and expansive windows that allow natural light to fill the space, set against a backdrop of blue skies and scattered clouds.

Condo in Innisfil

4.99 out of 5 average rating, 216 reviews

Boho by the Bay

BlogTO writes: " Friday Harbour Resort is a vibrant, upscale destination...That's perfect for a quick getaway..., with plenty of cool restaurants and shops, a waterfront pedestrian village, and year-round recreational activities." I encourage you to search eventsatfridayharbour to see what is seasonally available. if after searching, you still have questions or need clarification, please ask!

Guest favorite

A calm beach scene at sunset is depicted, with golden hues reflecting on the water. A sandy shoreline is visible, along with a playful dog standing at the water's edge, gazing towards the horizon. The sun casts a warm glow over the tranquil landscape.

Condo in Collingwood

4.94 out of 5 average rating, 683 reviews

Modern & Chic Sanctuary Suite in Collingwood

Unit located by Living Stone Golf Resort, minutes away from downtown Collingwood, and 10 mins from Blue Mountain/Scandinave Spa. Our renovated condo offers modern-chic elegance. Enjoy 625 sq ft of privacy with two bedrooms and one bathroom with tub and shower. There is also a sofa, electric fireplace, Netflix and basic cable, WIFI, en-suite washer-dryer. Outdoor terrace with garden views.