Luxury rentals in The Great Lakes

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Top-rated luxury holiday rentals in The Great Lakes

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Luxe

Home in Lakeside

4.93 out of 5 average rating, 111 reviews

Landmark Home 1 Blk from Lk MI w/Game Rm + EV Chgr

Sumptuous 4 BR/2.5 BA vacation home, just 1 block from Lake Michigan. Fully refurbished with reclaimed flooring, antique beams, custom doors, and fixtures. High-end kitchen, dining, and living areas with French windows. Living room features a stone fireplace, stylish couches, and a wide-screen TV. Three ground-floor bedrooms and baths with a second-floor bunk bed loft. Detached garage is a posh game room with high-end tables and a big TV. Covered patio, 4-seat dining, and bluestone courtyard. This property has been selected for inclusion in The 100 Collection, a global designation awarded to only the top professionally managed vacation rentals based on consistent quality and service. Classy, awe-inspiring, and sumptuous, this 1928 4 BR/2.5 BA vacation home, located just a block from Lake Michigan in “Harbor Country,” was once a local retail gathering place. Recently refurbished into a stunning residential home, it includes gorgeous reclaimed flooring from antique beams, custom doors, light fixtures, and hardware, as well as top-of-the-line plumbing fixtures. The kitchen-dining room-living room area—a massive, superbly well-lit space—features entire walls of French windows, original glass-block, and a wide array of seating options for meals: 4 chic stools at the white marble island, 4 leather seats around a circular marble coffee table, and a 10-seat reclaimed wood dining table. The beautifully lit living room has a classic stone fireplace at its center, stylish (yet ultra-comfortable) couches and chairs, and a wide-screen TV. In addition to the three bedrooms and bathrooms on the ground floor, there’s a second-floor sleeping loft, perfect for kids with cute bunk beds and a real (mini) teepee. All bedrooms feature top-quality bedding and linens, ensuring a sound sleep and sweet dreams for you and your guests. Black Door Bungalow can sleep up to 10. MAIN FLOOR Primary Bedroom: 1 King bed Bedroom 2: 1 Queen bed Bedroom 3: 1 Queen bed UPSTAIRS FLOOR Bedroom 4: Full-over-full bunk bed that sleeps 4 Another “extra” is the detached garage, which has been turned into a posh game room, with high-end shuffleboard and foosball tables, a big-screen TV, and a sound system. The exterior—featuring a spacious covered patio with cozy rattan couch, chairs, and a 4-seat dining table, leading to a bluestone courtyard—has been extensively landscaped with lush plantings, trees, and professional lighting. The home also includes a high-end kitchen, EV charger, and laundry appliances. In addition to being an easy walk from a majestic, crystal-sand Lake Michigan beach—and a super-short drive to popular beaches like Pier Street Beach and Cherry Beach—you and your guests can also enjoy the many activities afforded by being near Warren Woods State Park, which offers all sorts of woodland hiking and biking trails. The region’s largest recreational harbor provides countless water-related excursions and rentals, from fishing trips to boat, kayak, jet-ski, and paddleboard rentals, as well as day and evening cruises. There’s also the Acorn Theater, a local treasure for live performances by nationally recognized music artists, and a number of nearby breweries, wineries, brew pubs, and even an award-winning distillery for you to check out. Of course, you and your guests can also enjoy sampling to your heart's content the many popular restaurants, cafes, art galleries, boutiques, and antique shops just a hop, skip, and a jump away in Union Pier and downtown New Buffalo.

Luxe

Home in Highland Park

Champions Point Legendary Living

Live like a legend at 2700 Point Ln! This estate was built with privacy, security, and luxury in mind - a private oasis on 7.39 acres surrounded by mature pines, fenced and gated. Enjoy putting on your professional grade putting green, fishing in your private pond stocked with bass and bluegill, and swimming in your zero-entry infinity edge pool! Inside enjoy your movie theatre, commercial gym, cigar lounge, wine cellar, pool tables, bars, salon, salt water aquariums, and full basketball court!

Luxe

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

Cottage in Bracebridge

5 out of 5 average rating, 4 reviews

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

Home in West Olive

5 out of 5 average rating, 17 reviews

Luxe Family Estate | Lake Michigan + Beach Gear

Welcome to Pigeon Lake Luxury. A private beach estate near Lake Michigan. Sunset decks, family-ready amenities, and peaceful water views meet five-star stillness. Fully stocked with beach gear, baby items, and luxe touches. Designed for rest. Built for memories. Includes private beach parking, toddler gear, high chair, coolers, towels, boardwalk access, and concierge-level hospitality. Ideal for family retreats, peaceful escapes, luxury vacations, romantic stays, and unforgettable lake days.

Luxe

Flat in Chicago

4.86 out of 5 average rating, 28 reviews

Luxury Designer Penthouse|Private Deck|Gold Coast

BRAND NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy your own penthouse in Chicago's Gold Coast-the city's center of nightlife, restaurants, and shopping. In a completely redeveloped luxury brownstone, your 3 bedroom/3 bathroom penthouse offers ultra high-end appliances, design, and finishes, with two private patios/decks (truly unique amenity in Chicago) and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between!

Luxe

Home in Dysart and Others

5 out of 5 average rating, 29 reviews

NEW - BirchHouse - Modern Lakefront Luxury

Welcome to BirchHouse. A contemporary, architecturally designed lake house in the heart of Ontario's cottage country - the Haliburton Highlands. Perched cliff side with panoramic views over pristine waters, supreme privacy and tranquility are in abundance. Simple, intentional design with nature as a backdrop inspires a slower pace of life. A warm space to connect with loved ones, create lasting memories, and embrace relaxed luxury. Licensed by Dysart et al: STR-24-00017

Luxe

Home in Toronto

5 out of 5 average rating, 13 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

Home in Bracebridge

4.95 out of 5 average rating, 21 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

Apartment in Chicago

5 out of 5 average rating, 8 reviews

Ultra Modern Luxury - New Construction 4 Bedrooms

🌟 New 4BR Duplex in Uptown/Edgewater! 🌟 This ultra-modern 2500+ SF duplex is steps from Lake Michigan, Andersonville, and vibrant dining, shopping, & nightlife. Featuring 4 bedrooms and 2.5 baths, the condo boasts a private rooftop deck with a fire pit 🔥, loungers, and patio seating. Just ½ block to the Red Line 🚇. Garage parking included. Concierge services available. Ideal for short-term stays, executives, or insurance clients. Enjoy comfort & convenience! ✨

Luxe

Villa in Innisfil

5 out of 5 average rating, 30 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

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.