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Condo holiday rentals in Simcoe County

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Top-rated condo rentals in Simcoe County

Guests agree: These condos are highly rated for location, cleanliness and more.

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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

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!

ValueFamilyBeach

5.0 out of 5 average rating, 240 reviews
Top 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

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

ValueLocationHeating

4.95 out of 5 average rating, 215 reviews
Guest favourite
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

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

FamilyLocationView

4.93 out of 5 average rating, 170 reviews
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 Horseshoe Valley

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.

FamilyLocationOutdoor spaces

4.98 out of 5 average rating, 130 reviews
Guest favourite
Condo in Innisfil

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

ValueFamilyView

4.93 out of 5 average rating, 244 reviews
Top Guest favourite
Condo in Innisfil

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.

ValueLocationCondition

4.99 out of 5 average rating, 136 reviews
Top Guest favourite
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

Cozy Residence with Walkout to Courtyard

Experience Lakeside Luxury! Located on the ground floor with walkout access to the courtyard with a pool(closed for the season), hot tub(currently closed for repair) fire pit, and lounge areas. Everything you need is just steps away including Starbucks, LCBO, groceries, fine dining and so much more. Enjoy the live music on the pier, golfing, water activities(seasonal), and special events. Check out the Friday Habour website for a calendar of events throughout the year.

LocationValueParking

4.96 out of 5 average rating, 111 reviews
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 Horseshoe Valley

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.

FamilyValueIndoor spaces

4.99 out of 5 average rating, 141 reviews
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 Blue Mountain Resort Area

Cozy & Charming Retreat at Blue Mountain

***Pool closes on October 13, 2026*** Enjoy a stylish stay at Rivergrass Resort, centrally located at Blue Mountain. This upgraded retreat offers beautiful mountain views and backs onto the 18th hole of the award-winning Monterra Golf Course. With modern finishes and all the comforts of home, it’s the perfect place to unwind after a day of skiing, golfing, or exploring the Village. Short Term Accommodation License #LCSTR20210000237

FamilyValueBathroom

4.93 out of 5 average rating, 417 reviews
Top Guest favourite
A living room features a flat-screen television mounted on a stone accent wall above a small fireplace. A cozy armchair and a wooden dining table with matching chairs are visible. Natural light filters in through a window adorned with soft curtains.
Condo in Horseshoe Valley

Pet-friendly, 1 BR condo in Horseshoe Valley

All-season Condominium in Horseshoe Valley. Spacious BR with ensuite. Living room with fireplace, dining space, sofa bed. Private balcony, kitchen with all the necessities. Walk to the new Vetta Nordic Spa. Skiing , golfing , hiking & biking trails, treetop trekking, restaurants, groceries- 5 min drive Barrie , Orillia , Wassaga beach are 20 min. drive( beach #3 is PET FRIENDLY) Please note: we are NOT able to accept cats!

ValueLocationNearby

4.96 out of 5 average rating, 211 reviews
Top Guest favourite
Condo in Innisfil

JillBilly 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!

LocationFamilyPool

4.99 out of 5 average rating, 344 reviews
Top Guest favourite
Condo in Collingwood

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.

FamilyLocationWi-Fi

4.94 out of 5 average rating, 868 reviews

Popular amenities for Simcoe County condo rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Weekly condo rentals

Superhost
An open living space is displayed, featuring a comfortable sofa adorned with throw pillows. A central coffee table rests atop a patterned area rug, while a wooden dining table with seating for six is visible. The kitchen area is positioned at the back, showcasing modern appliances.
Condo in Horseshoe Valley

Stunning Suite in Horseshoe Valley

FamilyValueHospitality

4.86 out of 5 average rating, 120 reviews
Top Guest favourite
A spacious open-concept living area is highlighted, featuring a large dining table set for meals. The kitchen is equipped with modern appliances and black cabinetry. Natural light enters through multiple windows, enhancing the inviting atmosphere of the space.
Condo in Blue Mountain Resort Area

Lovely 3 Bedroom Condo with Stunning View and Pool

ValueLocationAmenities

4.99 out of 5 average rating, 239 reviews
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 Blue Mountain Resort Area

Maple & Mountain | Pool/Hot Tub/Shuttle/WalkToBlue

FamilyLocationAccess

4.96 out of 5 average rating, 1034 reviews
Superhost
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 Blue Mountain Resort Area

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

ValueFamilyDecor

4.83 out of 5 average rating, 482 reviews
Superhost
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

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

LocationFamilyCheckout

4.86 out of 5 average rating, 205 reviews
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

Resort Condo in Friday Harbour

FamilyLocationSkiing

4.88 out of 5 average rating, 352 reviews
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

Golf, Spa & Fall Vibes Getaway at Friday Harbour

ValueLocationLayout

4.98 out of 5 average rating, 140 reviews
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 Blue Mountain Resort Area

Blue Vista | Pool/Hot Tub/Shuttle/WalkToBlue

LocationFamilyTV

4.94 out of 5 average rating, 663 reviews

Pet-friendly condo rentals

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

Designer Condo with beautiful harbour view.

ValueLocationOutdoor spaces

4.94 out of 5 average rating, 261 reviews
Guest favourite
The living room features two sofas and a coffee table, set against a backdrop of large windows offering views of the Monterra Golf Course. A fireplace adds warmth to the space, while light drapes and accents enhance the room's inviting atmosphere.
Condo in Blue Mountain Resort Area

Alpine Breeze Getaway - Hot Tub + Golf Views

LocationFamilyBiking

4.87 out of 5 average rating, 105 reviews
Guest favourite
Condo in Innisfil

Friday Harbour Penthouse | Pool & Marina

ValueFamilyAccuracy

4.88 out of 5 average rating, 235 reviews
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 Blue Mountain Resort Area

Modern Studio, close to Village

FamilyLocationComfort

4.86 out of 5 average rating, 523 reviews
Superhost
The studio features a spacious bed adorned with white linens, flanked by two wall-mounted lights casting a serene glow. A mountain-themed mural in shades of teal and blue creates a calming backdrop, while a small table and a white dresser provide functional accents.
Condo in Blue Mountain Resort Area

Creekside Smart Studio at Blue Mountain

LocationValueOutdoor spaces

4.84 out of 5 average rating, 732 reviews
Guest favourite
The living area displays comfortable seating, featuring a dark blue tufted sofa and a black sofa. A wooden coffee table is centered on a light area rug, while a stone fireplace adds warmth. Large windows with light-colored curtains allow for natural light.
Condo in Horseshoe Valley

Elegant 2Suite Condo,Jacuzzi,pool,Horseshoe valley

FamilyLocationHospitality

4.88 out of 5 average rating, 48 reviews
Guest favourite
Condo in Innisfil

Nature trail views with cozy patio and firetable!

FamilyLocationPool

4.92 out of 5 average rating, 75 reviews
Top Guest favourite
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

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

LocationValuePets

4.99 out of 5 average rating, 76 reviews

Condo rentals with a pool

Guest favourite
Condo in Blue Mountain Resort Area

Sunny Days | Hot Tub, Walk & Shuttle to Blue Mtn

LocationValueWi-Fi

4.9 out of 5 average rating, 132 reviews
Superhost
A modern studio chalet combines farmhouse elements with luxury furnishings. A cozy sofa in front of a wooden accent wall faces a king-sized bed adorned with neutral tones. The kitchen area includes a breakfast bar with stools, enhancing the open layout and functionality.
Condo in Blue Mountain Resort Area

Blue Mountain Studio with King Bed

FamilyLocationBeach

4.79 out of 5 average rating, 426 reviews
Guest favourite
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 Blue Mountain Resort Area

Blue Mountain Escape, WIFI, Base of North lift

LocationValueAccess

4.81 out of 5 average rating, 228 reviews
Top 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 Blue Mountain Resort Area

The Blue Mountain's Dream Escape|Hot Tub|Xmas Tree

LocationValueOutdoor spaces

4.93 out of 5 average rating, 322 reviews
Superhost
A cozy living space features a flat-screen TV mounted on the wall above a wooden media console. There are two small tables in front of a comfortable grey sofa, with a light neutral rug underneath. The kitchen area is visible, showcasing modern appliances and bar stools.
Condo in Blue Mountain Resort Area

TIMBUK-BLUE Ski In/Ski Out

LocationValueHeating

4.8 out of 5 average rating, 208 reviews
Superhost
A bright living room is displayed with a gas fireplace and comfortable seating arranged around a circular coffee table. Large windows allow natural light to fill the space, while a cozy area rug adds texture. Decorative wall art enhances the inviting ambiance.
Condo in Blue Mountain Resort Area

Clearview Chalet • Modern 3BR • Mountain Stay

FamilyLocationOutdoor spaces

4.79 out of 5 average rating, 150 reviews
Guest favourite
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 Blue Mountain Resort Area

Close to Village, 2 Bedrooms , Rivergrass

LocationValueSleep quality

4.88 out of 5 average rating, 223 reviews
Top Guest favourite
A cozy bedroom features a spacious bed with light-colored linens and two decorative pillows. Nightstands with lamps are positioned on either side, providing soft illumination. A framed artwork hangs on the wall above the bed, and large windows allow natural light to fill the space.
Condo in Innisfil

Beautifully Furnished New Condo at Friday Harbour

ValueLocationBathroom

4.9 out of 5 average rating, 239 reviews

Destinations to explore