Luxury rentals in Simcoe County

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Top-rated luxury vacation rentals in Simcoe County

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Luxe

Cottage in Oro Station

Luxury Estate on Lake Simcoe w Infinity Pool

Stunning Modern Luxury on Lake Simcoe in Kempenfelt Bay (the "Hamptons of the North"). 1 Hr to Toronto; 15 Mins to Barrie, Golf, Skiing (Horseshoe, Moonstone), Spas & More. Skip the Traffic to Muskoka! 6,000+ Sq Ft Cottage w 4 Bdrms (6 Beds); 5 Bthrms; Chef's Kitchen; Sun-Filled 20 Ft High Great Room; 2 Offices; Full Gym; Games Room w Pool & Darts; Putting Green; Outdoor Kitchen; Gas BBQ; Boathouse; Firepits. South Facing w Deep Water Swimming. 5-Star Hotel Amenities Provided. No Parties.

Luxe

A spacious lakefront villa is set against a backdrop of lush greenery. The exterior features large windows and multiple doors leading to a deck, where comfortable seating is arranged. The manicured lawn offers an inviting space for outdoor activities.

Villa in Innisfil

5 out of 5 average rating, 31 reviews

Luxury Waterfront Cottage

Welcome to our lakefront vacation rental! Enjoy the full spectrum of morning golden hour colours in this premium waterfront villa on Lake Simcoe. This premium house on a private road is situated in a quiet neighbourhood, which offers a peaceful environment for time well spent with a group of friends or large family gatherings. This house is a unique east-facing spot surrounded by greenery and fresh air. It is minutes from happening Friday Harbour resort.

Luxe

A modern living area features a sleek black fireplace as the central focus, accompanied by a large wall-mounted television. Light-colored sofas with soft cushions surround a circular wooden coffee table, while natural light filters through sheer curtains, enhancing the open and airy feel.

Villa in Georgina

5 out of 5 average rating, 13 reviews

Georgina Waterfront Villa

Welcome to our brand new designer estate, located on the waterfront of Lake Simcoe. This coastal-inspired retreat offers a perfect blend of relaxation, entertainment, and luxurious amenities for a group of up to 12 people. In addition to various lakeshore activities your friends and family can enjoy our state of the art spa area, relax in the hot-tub, and explore the game room with pinball machine, pool, foosball and air hockey!

Luxe

Cottage in Gravenhurst

5 out of 5 average rating, 18 reviews

Modern Luxury Cottage | Sauna, Hot Tub, Lakefront

Newly built modern luxury Muskoka cottage with stunning design on a private 5-acre lot. 450 ft lakefront, sandy beach, huge dock, weed-free deep water, sauna, hot tub, outdoor shower, canoe, kayaks, paddle boat, SUP, chef’s kitchen, Starlink WiFi, workspace, BBQ, firepit and EV charging. Swim, fish, relax, and play—perfect for families or groups seeking comfort, style, and fun.

Luxe

The exterior of the log home displays a combination of natural wood beams and modern design elements. A spacious balcony overlooks landscaped areas, while large windows allow for views of the surroundings. The property is framed by trees displaying autumn foliage, enhancing its rustic charm.

Home in Gravenhurst

Unforgettable log build on Lake Muskoka - 8 bdrms

Out of this world luxury log-home with 7 bedrooms and 6 bathrooms, located on beautiful Muskoka Bay on Lake Muskoka near Gravenhurst. High-end finishes combined with the charm of a log cabin in this very large & brand new cottage. A dream come true!