Luxury rentals in Lake Simcoe

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Top-rated luxury vacation rentals in Lake Simcoe

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Luxe

A modern living area features a spacious sectional sofa, paired with accent chairs, all arranged on a textured area rug. Floor-to-ceiling glass windows frame views of the surrounding landscape, while wooden ceiling beams and warm lighting create a cohesive design.

Place to stay in Caledon

Peak House

Hills and valleys stretch for 100 acres around this design-forward hilltop home in the Ontario countryside. A pool and hot tub sit mid-lawn, and a firepit anchors a covered outdoor seating area. Glass walls contrast moody rooms splashed with dark stone and wood paneling. It’s a few minutes to the village of Caledon and less than an hour to dining, shopping, and entertainment in downtown Toronto. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Master: King size bed, Ensuite bathroom with standalone shower and bathtub • Bedroom 2: Queen size bed • Bedroom 3: Twin size bed, Shared access to hallway bathroom, • Bedroom 4: 2 Twin over bunk beds, Ensuite bathroom with standalone shower • Bedroom 5: Queen size bed, Shared access to hallway bathroom, STAFF & SERVICES Extra Cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

Luxe

A built-in hot tub is positioned on a wooden deck, surrounded by lush greenery and enhanced by evening lights. The modern home features large windows and a spacious outdoor dining area nearby, set against a serene waterfront landscape.

Home in Brechin

4.89 out of 5 average rating, 9 reviews

Waterfront HotTub PoolTable FirePit Kayaks BoatLux

Welcome to The Villa - luxury waterfront escape. This custom-built waterfront home stuns with rich millwork, natural textures, and designer finishes throughout. Soak in the hot tub, gather by the fire pit, or dine alfresco with beautiful views. Inside, enjoy a pool table, Pacman Arcade, oversized Jenga, and Connect 4 for nonstop fun. With a BBQ, outdoor seating, and elegant contrast details, this home is the perfect blend of comfort, entertainment, and lakeside serenity. Pontoon Boat Add. Charge

Luxe

Cottage in Bracebridge

Chroma, on the Muskoka River

Allow Chroma to infuse you and your guests with the perfect modern cottage escape. A stone's throw to 5-star culinary pleasures, craft breweries, and bakeries in one of Muskoka's largest communities. Immerse yourself in the refined design of this 5-bedroom home. Experience the bliss with on-site fitness, sauna, river activities, and provided water gear. Relax in the hot tub or by the fire pit, and savour entertainment indoors. Chroma is the epitome of Muskoka luxury and practical enjoyment.

Luxe

A bright living area features large glass windows that provide expansive views of the surrounding landscape. Soft seating arrangements, including a sectional sofa and armchairs, create a comfortable space. A wooden coffee table holds decorative items, enhancing the inviting atmosphere.

Home in Nobleton

King Vista

This Scandinavian inspired vacation home is the perfect escape from the city. Located just 40 km north of Toronto, you will feel like you're a million miles away but within an hour's drive. This brand new sustainably built home invites you to come and enjoy the nature of the 50 acre estate while minimizing your carbon footprint. With endless nearby hiking trails, a heated saltwater pool and hot tub, everything is here for your enjoyment! Copyright © Luxury Retreats. All rights reserved.

Luxe

Home in Bracebridge

4.94 out of 5 average rating, 18 reviews

Modern Riverfront Escape w/Sauna, Gym, Dock

Welcome to our modern, spacious retreat along the beautiful Muskoka River. This 4-bedroom, 4.5-bathroom house sits on over 2 acres of tranquil land, offering the perfect blend of comfort, luxury, and nature. Start your day on the Muskoka River with our paddle boards and kayaks, or unwind with a good book from our collection. The sauna provides a perfect place to relax after a day of outdoor activities. The perfect blend of outdoor activity and tranquil surroundings.

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, 26 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 cottage is surrounded by lush greenery, showcasing a blend of stone and wood materials. The exterior features large glass windows that invite natural light and provide views of the landscaped pathway and tranquil surroundings.

Home in Muskoka Lakes

Stillwater Shores, Bala

Welcome to Stillwater Shores in beautiful Bala, Ontario—a perfect blend of modern elegance and Muskoka charm. Designed for both relaxation and entertainment, this exceptional property offers 6 spacious bedrooms, 3 full bathrooms, and a powder room, comfortably sleeping up to 12 guests. Located minutes away from downtown Bala, this property is ideally situated for enjoying quiet moments in nature and exploring Muskoka's finest experiences.

Luxe

A spacious cottage is surrounded by lush greenery, located just steps from the serene lake. The property features a wooden dock extending into the water, while the calm surface reflects the vibrant trees and sky above.

Cottage in Gravenhurst

4.65 out of 5 average rating, 17 reviews

Muskoka Waterfront Retreat

Cozy and luxurious, our newly renovated 2023 cottage is ready to greet you with the best conditions for a wonderful family retreat. With over 200 feet of stunning lake frontage, this spacious and well-built property offers a truly enchanting stay. Relax and rejuvenate in the private sauna, complete with its own hot tub and cold plunge. Get ready for an unforgettable getaway filled with comfort, serenity, and unmatched indulgence.

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, 8 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

An open recreational area is showcased, featuring a sleek billiards table at its center. Large glass doors allow natural light to fill the space while providing a view of the surrounding landscape. A contemporary kitchen and living area are visible in the background.

Home in Muskoka Lakes

Twilight Delight, Lake Joseph

Welcome to Twilight Delight, an exquisite family compound designed to offer the ultimate luxury retreat. Nestled amidst the scenic beauty of Muskoka, this contemporary estate resonates with modern elegance and timeless charm. With three unique buildings – the Main Cottage, Boathouse, and Garage – Twilight Delight provides an unparalleled experience for families seeking a serene and luxurious escape.