Villa holiday rentals in Simcoe County

Executive Villa - Year Round Swim Spa & Game Room

Mediterranean inspired country villa: Get away from the big city and unwind in this luxurious custom built bungaloft - total 6000 Sq Ft livable space . Situated in an exclusive estate community enclave and sits on a private 2 acre property. The residence boasts a high-end kitchens, year round swim spa (outside) and game room (basement). Enjoy great shopping at nearby Tanger Outlet Mall. A short drive to Cooks Bay Marina, & only 20 minutes from Canada’s Wonderland & Snow Valley Ski resort.

Cedar Escape • Sauna • 10-Acre Private Forest

(Lic. STR2024-0005) Welcome to your private 10-acre forest estate, an exclusive sanctuary where refined luxury meets pristine nature. Wander serene woodland trails, refresh beneath the open-air forest shower, and gather fireside under a canopy of stars. Indulge in the soothing sauna, unwind poolside in complete privacy, and embrace the rare stillness surrounding you. Just minutes from the city, yet utterly secluded—offering elevated comfort, tranquility, and seamless high-speed connectivity.

Nordic Elegance Villa in Muskoka

Welcome to Nordic Elegance Villa at Muskoka Bay Resort! This villa showcases Scandinavian design and offers a sophisticated ambiance. As a 5-star property, it is designed to exceed your expectations, with amenities tailored for families. Explore a wide array of Muskoka Bay Resort's amenities, including a swimming pool, sauna, trails, and golfing (ranked #1 golf course in Ontario). Minutes away from local parks and Muskoka Steamships/Discovery Centre. Bring the family and enjoy all the fun!

Charming Mid-Century Villa on 10 Acres Forest Land

We call it House of Wonders! book with us to relax and unwind in peace & tranquillity. Enjoy full privacy on 10 acres w/scenic forest trails, garden, patio with gazebo lit at night, 4 different outdoor fire pits, various outdoor sitting and dinning areas. Read your favourite book on the hammock, get busy with bird watching or take advantage of the equipped indoor gym. This 2 storey villa with brick interiors has lots of characters with a fully equipped kitchen, freestanding bathtub & more

The Family Escape Townhome

Conveniently located in Collingwood, Ontario only 1.5 hours from the GTA, this home is a 5 minute drive to Blue Mountain Resort, a 7 minute drive to Northwinds Beach & 20 minute drive to Wasaga Beach (the largest fresh water beach in the world!). Enjoy hiking/biking trails, golf and so much more! Set your day’s agenda from hitting the slopes, to relaxing at the spa. This home will make you feel warm and welcomed to the four-season destination of Collingwood & our neighbour Blue Mountain!

March Break Steps to Village 2 decks BBQ Sauna KQQ

Spring skiing time has begun! The Blue Mtn Village is bustling steps away from our condo.Perfect time to experience and make memories at Blue Mtn Village.Enjoy 2 decks, 1 facing Mtn slopes with BBQ.1 facing Monterra Golf Course.T 7 guests:1 person on new futon in living room (2 littles to get to 8).We provide the bedding.1 king Master.with electric sauna 2/,Queen bedrooms..Open concept living room w/gas fireplace and 2 Smart TV’s/dining room/kitchen/laundry/2 free parking spots. 5 stars

ScandinaVilla Retreat

ScandinaVilla, an Exquisite Scandinavian-Style Private Villa is surrounded by a lush forest landscape and nestled on the grounds of the sought after Muskoka Bay Golf Resort community. Enjoy golfing, hiking trails, cycling, and water activities in nearby nature & beaches in the summer; and snowshoeing, cross country skiing, ice fishing and ice skating in the winter months. Visit the clubhouse and benefit from all its amenities including state of the art gym & 5-star dining experience!

Luxury Collingwood Getaway

Exquisite Custom Built Bungalow w/ 4 Beds, 4 baths & luxurious finishes throughout. ( 1 king, 1 queen, 1 double bed, 1 queen blowup set) Located in Collingwood, this stunning property has a balance of indoor and outdoor space. Unwind in the inviting hot tub, perfect for starlit evenings & soothing relaxation. This property offers a convenient proximity to Collingwood's finest amenities, hiking trails, & ski resorts are just a short drive away, ensuring year-round enjoyment.

Entire Villa with beautiful fenced backyard

This cozy and elegant villa is situated on 0.5 acre with spacious first-floor master bedroom suite, lovely sunroom, beautiful fenced backyard, fire pit and long driveway. Awesome location with lots of greenery, fall colours and fairy tale snow scenes! Everything is close by but you are in the peaceful countryside. 3 mins from HWY 400 and 30 mins from airport. No any kind of party is allowed here and no any street parking. Thanks for your great understanding!

Beautiful Getaway Location - Cuddles Cove

Enjoy a all year round getaway either personal or corporate retreat at this spacious, well equipped Bungalow located short minutes walk from beautiful sand beach access. This newly built cottage is approx 5,000 Sqft with an additional 1,000 Sqft covered balcony offering accommodations of 6 queen beds, 1 Luxury full kitchen, 1 BBQ and lots of entertainment! Enjoy a nice Quiet getaway in the lovely community of Tiny! STRTT-2026-135

The Sandals Of Tiny Hottub, Sauna, White SandBeach

Relax at this tranquil, newly refreshed 5-bedroom all-seasons cottage in Tiny Township on Georgian Bay. Escape the city and unwind with family and friends in the outdoor spa. Enjoy pristine beaches in the summer and ski slopes in the winter. Stay comfortable indoors with central AC, heating, a fireplace, and a big screen TV in the living room. No parties or events on premises.

Luxury Resort Villa in Muskoka

Escape to our brand new 3-bedroom villa at Muskoka Bay Resort! This serene, two-level end-unit comfortably fits families or groups. Enjoy modern comforts, a fully-equipped kitchen, and stunning golf course views. Guests have access to the resort's sparkling pool, sauna, and lake access. A perfect year-round retreat just moments from Lake Muskoka and Gravenhurst Wharf.