Condo holiday rentals in Simcoe County

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!

Value · Location · Quiet

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

Welcome to Maple & Mountain, a cozy 2-bedroom, 2-bathroom retreat with warm Canadiana charm, a fireplace and stunning golf course and mountain views, just a 5–7 minute walk to Blue Mountain Village. Unwind by the fire or enjoy the view after a day of skiing, hiking or exploring Blue. *Shuttle service *Year-round hot tub with indoor changeroom & washrooms *Seasonal outdoor pool- closing Tues October 13 2026 *SMART TVs, Wi-Fi & cable *Equipped kitchen *Booster seat & Pack ’n Play *Self check-in

Family · Value · Checkout

Golf, Spa & Fall Vibes Getaway at Friday Harbour

Welcome to our exquisite 2BR/2BA oasis, where relaxation knows no bounds. Embrace the tranquility of our inviting space. Indulge in the comforts of home with a fully equipped kitchen, cozy living area and two private bedrooms designed for restful nights. Soak in the hot tub's warmth, swim and lounge by the pool or gather round the fire pit for memorable conversations under the stars. Your perfect vacation retreat awaits. Book now to experience luxury, comfort & outdoor delight like never before!

Family · Location · Accuracy

Blue Vista | Pool/Hot Tub/Shuttle/WalkToBlue

Welcome to Blue Vista, a bright 2-bedroom, 2-bathroom retreat with golf course and mountain views, just a 3–5 minute walk to Blue Mountain Village. Relax on the balcony or enjoy the bright, comfortable space after a day of skiing, hiking or exploring Blue. *Shuttle service *Year-round hot tub with indoor changeroom & washrooms *Seasonal outdoor pool- closing Tuesday October 13 2026 for the year *Fireplace *SMART TV, Wi-Fi & cable *Equipped kitchen *High chair & Pack ’n Play *Self check-in

Value · Family · Barbecue

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

Location · Family · Sleep quality

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.

Value · Family · Hot tub

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.

Family · Value · Walkability

Stunning Suite in Horseshoe Valley

Sitting on top of Horseshoe Valley, this stunning and unique condo sets the stage for a memorable and cozy trip. This suite has it all! - Fully stocked kitchen - 6-person dining table - Pull-out couch + loveseat + lounge chair - Cozy fireplace - Comfortable king-size bed - 2-person soaker tub + shower - Private Balcony - Year-round indoor/outdoor pool with hot tub and sauna - Fully equipped gym Minutes away from Vetta Spa, Horseshoe Valley, golf courses and more!

Location · Family · Shared spaces

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.

Location · Value · Hiking

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!

Value · Family · Checkout

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!

Location · Value · Kitchen

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.

Family · Location · Quiet