Luxury rentals in The Great Lakes

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Top-rated luxury vacation rentals in The Great Lakes

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Superhost

Rental unit in Chicago

4.4 out of 5 average rating, 5 reviews

WOW! 3000ft² PH w/ views to The Bean @MichiganAve

Tired of high-priced stays that lack true exclusivity and comfort? Stay in the Most Exclusive Penthouse in Chicago Welcome to The Orion! a 3000ft² penthouse in the 21st floor located in Downtown, right across from The Bean and Millennium Park. This building offers a private amenity floor just for the penthouse collection residents. Enjoy top-tier furnishings from CB2, and linens and towels by Frette. Only for the ELITE TRAVELER ★Guests Say This Is the Best Penthouse Money Can Buy★ The space

Luxe

Rental unit in Chicago

5 out of 5 average rating, 11 reviews

SURREALl! 3000ft² PH Floor 21View @MichiganAvenue

Tired of high-priced stays that lack true exclusivity and comfort? Stay in the Most Exclusive Penthouse in Chicago Welcome to The Stella! a 2643ft² penthouse in the 21st floor located in Downtown, right across from The Bean and Millennium Park. This exclusive building offers private amenity floor just for the penthouse collection residents. Enjoy top-tier furnishings from CB2, and linens and towels by Frette. Only for the ELITE TRAVELER ★Guests Say This Is the Best Penthouse Money Can Buy★

Luxe

Home in Toronto

5 out of 5 average rating, 5 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

Home in Dysart and Others

5 out of 5 average rating, 3 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

Villa in Innisfil

5 out of 5 average rating, 17 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.