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Condo holiday rentals in Simcoe County

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Top-rated condo rentals in Simcoe County

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Guest favourite
A comfortable outdoor balcony area features two lounge chairs and a glass-top table. Planters with various plants are positioned around the space, enhancing the natural ambiance. A textured rug adds warmth, completing the inviting outdoor setting.
Condo in Innisfil
4.94 out of 5 average rating, 192 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

Top Guest favourite
A glass table is set on a balcony, featuring an ice bucket holding a bottle of sparkling wine, accompanied by two elegant glasses. Soft string lights provide gentle illumination, enhancing the cozy atmosphere. A potted plant adds a touch of greenery.
Condo in Innisfil
5 out of 5 average rating, 217 reviews

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh and unwind in your very own private 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! Make Fire & Ice your next vacation destination and reconnect in a most romantic, relaxing suite!

Top Guest favourite
The living area features a modern design with a large flat-screen TV mounted above a stone fireplace. A cozy gray sofa is paired with a rustic coffee table and a comfortable orange armchair. Natural light enters through double glass doors leading outside.
Condo in Shanty Bay
4.98 out of 5 average rating, 117 reviews

Resort Condo (2 suites) near Horseshoe Valley

Enjoy a stylish experience in this spacious and serene space at Carriage Country Club Resort. A completely equipped designer condo with 2 suites for families looking for perfect vacation. Enjoy a peaceful night in your private Jacuzzi , prepare your own meal in the fully equipped kitchen. Few minutes drive to Horseshoe Valley Resort, and walkable to Vettä Nordic Spa. For Mount St. Louis Moonstone, only about 15 minutes drive away. Our heated indoor/outdoor swiming pool, available year-round.

Guest favourite
A modern living area features a spacious sectional sofa complemented by decorative pillows and a large coffee table. Natural light floods in through expansive glass windows, revealing a view of the private patio. Minimalist decor includes a geometric wall design and a stylish light fixture.
Condo in Innisfil
4.94 out of 5 average rating, 132 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!

Guest favourite
A spacious bedroom is highlighted by a large bed with crisp white linens and a decorative throw pillow. A cozy seating area features a light-colored sofa and lamps, adding to the calm ambiance. Framed artwork and a neutral color palette create an inviting atmosphere.
Condo in Oro
4.75 out of 5 average rating, 118 reviews

Lovely king size room with kitchenette

An inviting four-season natural playground surrounded by rolling hills and forested trails is located in a spectacular country setting. The Mount St. Louis Moonstone Ski Area is 12 km away, Barrie is 25 km away, and Toronto is 138 km away. Onsite amenities include a pool, fitness center, fire pit, and play area. Nearby, you can enjoy an array of fun attractions and activities for every season! Several convenient perks are available to provide you with the best and most comfortable stay.

Guest favourite
Condo in Innisfil
4.98 out of 5 average rating, 107 reviews

Stunning 1BR w Pool ~ Free Parking & Self Check-In

Embark on a journey of unparalleled luxury as you discover our exquisite suite, crafted to offer an escape that transcends the ordinary and leaves you refreshed. Experience opulent design, a full bedroom, a spacious living area with TV, high-speed WiFi, fully stocked kitchen, and a stunning balcony . Enjoy the breeze by the sun, and BBQ on our new electric grill. Access our outdoor pool and hot tub, no fees or reservations required. Additional fees may apply for 30 nights and more.

Guest favourite
An open-concept kitchen features sleek white cabinetry and a black granite island with three modern bar stools. Natural light fills the space through large glass doors, which lead to a balcony. A minimalistic design with potted plants enhances the welcoming atmosphere.
Condo in Innisfil
4.87 out of 5 average rating, 182 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 favourite
A modern kitchen area is featured, equipped with sleek cabinetry and stainless-steel appliances. A white island with two gray bar stools is positioned invitingly, while fruit is displayed on the island. Soft overhead lighting illuminates the space, creating a bright and functional environment.
Condo in Barrie
4.8 out of 5 average rating, 198 reviews

Newly renovated 1 bedroom condo with free parking

Enjoy staying in this stylish and cozy, newly renovated condo. Situated close to the many amenities Barrie and surrounding area has to offer! Enjoy parks, hit the trails, ski hills or head to the beach within minutes Easy access to the 400, Close to shopping, spas, many restaurants and the beautiful downtown waterfront area. Location will not disappoint. Main level with a walk out patio and fireplace. Equipped with a smart tv and Netflix for those cozy nights in.

Top Guest favourite
A cozy living area features a spacious sectional sofa adorned with soft pillows, complemented by a minimalist coffee table. Natural elements are highlighted by an accent wall showcasing a scenic forest mural. The nearby sleeping area includes a neatly made bed with fresh linens.
Condo in Shanty Bay
4.99 out of 5 average rating, 116 reviews

Wildwood HotTub+Indoor/Outdoor Pool+Sauna+GameRoom

Welcome to our cozy, modern condo in Horseshoe Valley — the perfect destination for families and groups of friends seeking adventure, relaxation, and unforgettable memories. Just a 2-hour drive from Toronto, our condo offers a prime location to experience it all. Whether you're hitting the slopes, unwinding at the Nordic spa, or exploring the outdoors with mountain biking, golf and tree-top trekking, you'll find everything you need for a perfect getaway.

Top Guest favourite
A cozy living area features a plush sectional couch and a wooden coffee table. Large windows provide views of the golf course, allowing natural light to brighten the space. A modern fireplace adds a welcoming touch, complemented by soft curtains and decorative wall accents.
Condo in The Blue Mountains
4.94 out of 5 average rating, 636 reviews

*Blue Mountain Village* Pool, Hot Tub, WalkToBlue

SHUTTLE, HOT TUB & SEASONAL POOL 360 degree views! We are a 3-5 minute walk to the Village with stunning views of the golf course and mountain! Perfect place to relax on the balcony or couch after a busy day of soaking up all Blue has to offer! ★Self-Check In ★Equipped kitchen, towels & linens ★ SMART TV, WIFI & CABLE ★ Games, high chair, PackNPlay ★ Resort hot tub with indoor changeroom and washrooms ★ Pool projected to open Monday June 15th 2026

Top Guest favourite
The living area is designed with a cozy sectional and an armchair, accompanied by a coffee table. A television is mounted above a stone fireplace. Large windows provide ample natural light and views of the surrounding hills and golf course.
Condo in The Blue Mountains
4.95 out of 5 average rating, 995 reviews

Stunning Mountain View- Pool, Hot Tub, WalkToBlue

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. ★ 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 projected to open Monday June 15th 2026

Top Guest favourite
The living room is designed with a cozy sectional sofa and a coffee table placed centrally. A mounted flat-screen TV is positioned above a white-brick fireplace. Natural light filters through sheer curtains, enhancing the welcoming feel of the space.
Condo in The Blue Mountains
4.93 out of 5 average rating, 389 reviews

Cozy & Charming Retreat at Blue Mountain

***POOL OPENING IS JUNE 19, 2026*** Enjoy a stylish experience at this centrally located retreat! Welcome to Rivergrass Resort with stunning views of beautiful Blue Mountain and backing onto the picturesque 18th hole of the award winning Monterra Golf Course. Our recently upgraded unit includes all the comforts of home with a modern flare. Short Term Accommodation License #LCSTR20210000237

Popular amenities for Simcoe County condo rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Weekly condo rentals

Guest favourite
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, 194 reviews

Blue Mountain condo in Historic Snowbridge

Top Guest favourite
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
4.94 out of 5 average rating, 249 reviews

Designer Condo with beautiful harbour view.

Guest favourite
The studio features a spacious living area with a comfortable sofa and a modern armchair. A king bed adorned with blue and yellow linens is positioned in the background. Natural light filters through the window treatments, enhancing the serene ambiance.
Condo in The Blue Mountains
4.84 out of 5 average rating, 461 reviews

Ski in/out @ North Creek W King bed! New Hot Tub

Top Guest favourite
A cozy bedroom features a spacious bed adorned with a decorative floral coverlet and an assortment of pillows in soft hues. An arched floor lamp provides warm lighting, while a piece of wall art adds a personal touch. Natural light filters through a window with light grey curtains.
Condo in Collingwood
4.99 out of 5 average rating, 166 reviews

K's Cozy Condo -Mins. to Ski, Trails, Shops, Beach

Guest favourite
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
4.87 out of 5 average rating, 329 reviews

Resort Condo in Friday Harbour

Top Guest favourite
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
4.99 out of 5 average rating, 113 reviews

Bohemian Luxury at Friday Harbour Resort Simcoe

Guest favourite
A bright kitchen and dining area feature a modern white countertop with seating, complemented by a wooden table surrounded by dining chairs. Natural light enters through several windows, and a clock adorns the wall, enhancing the space's functionality and warmth.
Condo in The Blue Mountains
4.95 out of 5 average rating, 175 reviews

Rustic Chic Renovated 2Bd Condo by Village

Guest favourite
The family room features high ceilings with large windows that provide ample natural light and views of the outdoors. A cozy sofa and various seating options surround a wooden coffee table, and a modern fireplace is complemented by a wall-mounted TV.
Condo in The Blue Mountains
4.92 out of 5 average rating, 239 reviews

First Tracks: Walk/Shuttle to Blue Mtn Village

Pet-friendly condo rentals

Guest favourite
A comfortable sofa with plush cushions is positioned in front of a small black table. Nearby, a spacious bed is visible, framed by soft lighting and a bedside lamp. Neutral-colored throw pillows add subtle color to the seating area.
Condo in The Blue Mountains
4.83 out of 5 average rating, 351 reviews

Blue Mountain Condo. The perfect staycation!

Top Guest favourite
A bright and airy living area showcases a plush white sectional sofa, paired with a modern light fixture above. Large windows invite natural light, while a sleek kitchen with bar seating is visible in the background. The backyard patio is furnished for outdoor gatherings.
Condo in Innisfil
4.99 out of 5 average rating, 75 reviews

Ground Floor w/ Large Terrance @ Friday Harbour

Superhost
Condo in The Blue Mountains
4.87 out of 5 average rating, 529 reviews

Enjoy the Summer Fun at Blue Mountain

Guest favourite
Condo in Innisfil
4.92 out of 5 average rating, 61 reviews

Nature trail views with cozy patio and firetable!

Guest favourite
The living area features a comfortable sectional sofa and a modern electric fireplace. A smart TV is mounted on the wall above a stylish media console. A geometric area rug adds texture to the space, while a decorative shelving unit displays greenery and art.
Condo in The Blue Mountains
4.89 out of 5 average rating, 121 reviews

The Parker Slopeside: Pool, Hot Tub, Tennis, Views

Guest favourite
A contemporary living area is equipped with a mounted television above a modern fireplace. A wooden table is positioned in the center, surrounded by stylish seating, including an armchair. The adjacent kitchen features blue cabinetry and modern appliances, providing a cohesive and welcoming space.
Condo in The Blue Mountains
4.87 out of 5 average rating, 497 reviews

Modern Studio, close to Village

Superhost
A spacious patio area features comfortable grey woven furniture, including a seating set with cushions and a coffee table. A dining table with chairs is positioned nearby. The space is surrounded by glass panels, and a vibrant green plant adds a touch of color.
Condo in Innisfil
4.81 out of 5 average rating, 107 reviews

Pet friendly 2 BR with a private terrace at FH

Superhost
A modern kitchen and living area feature an island with a sink, complemented by stylish bar stools. Floor-to-ceiling windows provide views of the surroundings and lake beyond. Neutral tones and natural light contribute to a bright and open layout.
Condo in Innisfil
4.94 out of 5 average rating, 52 reviews

Spectacular 2 BDRM Penthouse at Friday Harbour

Condo rentals with a pool

Top Guest favourite
A modern living area features a light-colored sofa adorned with decorative pillows, positioned next to a wooden coffee table. A striped area rug lies beneath, while a kitchen island with bar stools and stainless steel appliances is visible in the background.
Condo in Innisfil
4.97 out of 5 average rating, 118 reviews

Golf, Spa & Spring Vibes Getaway at Friday Harbour

Guest favourite
A cozy family room features a spacious gray sectional sofa and a wooden coffee table. Light-colored walls and a patterned rug create a welcoming atmosphere. In the background, a kitchen area is visible, equipped with modern appliances and seating for two.
Condo in The Blue Mountains
4.93 out of 5 average rating, 326 reviews

Cozy Studio Mountainside stay in Blue Mountains

Guest favourite
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, 147 reviews

The Fairway Chalet

Top Guest favourite
An open-concept living area is showcased, featuring a cozy sectional sofa and a stone fireplace with a modern TV mounted above. Natural light streams through large windows, illuminating the earthy tones of the decor. A circular wooden coffee table with decorative elements completes the inviting space.
Condo in The Blue Mountains
4.92 out of 5 average rating, 154 reviews

Highlands Lodge & Loft - Shuttle & Outdoor Pool

Guest favourite
A cozy living area is presented with two sofas and a fabric armchair, arranged around a wooden coffee table. A gas fireplace sits beneath a wall-mounted television. Large windows allow natural light, offering views of the surrounding landscape.
Condo in The Blue Mountains
4.93 out of 5 average rating, 296 reviews

The Blue Mountain's Dream Escape | Pool | Hot Tub

Guest favourite
A cozy living area features a dark sofa and a pull-out couch, complemented by colorful throw pillows. Natural light streams through multiple windows, highlighting the light wood flooring. A large flat-screen TV is mounted above a black fireplace, and a door leads out to a patio area.
Condo in The Blue Mountains
4.85 out of 5 average rating, 472 reviews

Mountain Side One Bedroom

Superhost
Condo in The Blue Mountains
4.76 out of 5 average rating, 494 reviews

Cozy Blue Mountain Retreat Ski in/ Ski out

Guest favourite
An open concept living area is showcased, featuring a large, comfortable sectional sofa facing a stone fireplace. The space is brightened by multiple windows, with dining and kitchen areas visible in the background. Stylish decor, including a wall clock, adds charm to the environment.
Condo in The Blue Mountains
4.96 out of 5 average rating, 190 reviews

Snowbridge Escape at Blue

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