Luxury rentals in Greater Toronto and Hamilton Area

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Top-rated luxury holiday rentals in Greater Toronto and Hamilton Area

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Luxe

The contemporary hilltop home is framed by lush greenery and colorful autumn foliage. A spacious stone patio outlines a pool area, and expansive glass walls reflect the natural surroundings, enhancing the design. The building showcases a dynamic roofline and large windows that invite light.

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 cozy living room is highlighted by a minimalist design, featuring a soft cream-colored sofa and a unique curved chair. A stone fireplace without a fire is framed by a light-toned wall, while a coffee table displays art books and decorative items. Natural light fills the space.

Home in Toronto

5 out of 5 average rating, 6 reviews

Beautiful Luxury Urban Retreat in Leslieville

Nestled in the vibrant Riverside/Leslieville neighborhood, this spacious 4-bedroom, 2-bathroom (+ 2 powder room) complete with an outdoor lounge/dining area (+ 1 parking spot). Is steps away to trendy eateries, cafes and bars, and just minutes away from Downtown Toronto and The Beaches. Ideal for your family, a group of friends or to host your bridal / wedding guests. Exquisitely decorated and curated by artist Anna Church. This exceptional property transcends the ordinary rental property.

Luxe

The modern Scandinavian home is showcased from an aerial view, featuring a spacious terrace with seating and a heated saltwater pool, illuminated with soft purple lights. Lush greenery surrounds the property, providing a serene backdrop against the evening sky.

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 Toronto

5 out of 5 average rating, 15 reviews

SwimSpaSauna Elevator PoolTableGits UltraLux7500SF

🌟 Welcome to The Icon—Toronto’s most luxurious short-term rental. A masterpiece in design and luxury, features over 7500 SqFt, Control4 Automation, 6 lavish bedrooms with walk-in closets & ensuites, 9 bathrooms, an elevator, a handcrafted staircase, a pool table, a 12-person swim spa, and a private sauna. Perfect for elite getaways, family trips, athletes & celebrities. Experience the city’s most iconic stay in the heart of Forest Hill. Book now and live like an Icon.

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

An elegant multi-story home is showcased against a backdrop of trees and dusk skies. The exterior features a blend of stone and stucco with large windows and a welcoming entrance. A well-maintained driveway leads to the attached garage, and landscaped gardens enhance the appeal.

Villa in Burlington

5 out of 5 average rating, 5 reviews

Lavish Luxury Experience

Elegant and luxurious, this multi-million dollar home in Burlington, Ontario is the perfect place to impress friends and loved ones, or coworkers on a work retreat. Only the finest white marble, brass fixtures, and designer furnishing made the cut at this masterpiece villa. Set on a secluded, nature filled plot, the kids will love playing in the grass and on the playground. Nearby, Toronto awaits. Copyright © Luxury Retreats. All rights reserved.

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, 12 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