Luxury rentals in The Great Lakes

Large Luxury House in River North!

Centrally located River North Penthouse in boutique building has everything you would want in city living. 2-story condo ALL 3 bedrooms featuring en-suites and an additional 1/2 bath. Large living room w/fireplace expands on to the outdoor deck with beautiful built-in grill, 2nd story features 2 bedrooms and a bright sun room with sofa bed. Spacious primary cozy fireplace along with steamed shower and jacuzzi tub. So much more with this luxury style living. Steps to all River North has to offer!

Landmark Home 1 Blk from Lake MI 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.

A Luxury Heritage |5BD & 4.5BA|HWY 404

Welcome to an architect-designed home, where three eras meet in timeless harmony — the charm of 1840, the craftsmanship of 1910, and the luxury of 2025. Thoughtfully curated and well designed living spaces invite connection, with cozy gathering spots, comfortable rooms, spa-like bathrooms, a designated work space, a children’s play area, yoga + exercise nook, and a shared bookshelf for all ages. Perfect for families, friends, groups, or retreats seeking warmth, beauty, and connection.

Stunning Home at Center of Rochester

This is a unique stunning home in the center of Rochester city. It is modernly furnished and perfect getaway for a family who would like to stay in a spacious, private, and sophisticated home in the heart of Rochester city. There is an expansive fully equipped kitchen, dining/living area, home office, two bedrooms with ensuite baths, and rooftop deck that showcases an unmatched Rochester skyline view. There is high-speed internet, multiple smart TVs w/ streaming, and 2 washers/2 dryers.

Muskoka Lakefront• Sauna • Fireplace• Chef kitchen

Welcome to Edgewater Cottage Muskoka, a brand-new luxury retreat on a private bay, less than two hours from Toronto & 10 minutes from Gravenhurst, with great restaurants, scenic hikes, golf, and amenities. Perfect for families, friends, couples, groups, retreats, or small corporate off sites. When booking please share a few details about your group. The property is for peaceful getaways and not available for parties. A signed rental agreement is required to confirm your reservation.

Luxury Waterfront Cottage

Crystal-clear turquoise water, clear as a tear – on Ontario’s most pristine lake. Private pool, sauna + cold plunge and cozy hot tub under the stars. Open-air kitchen with BBQ, gas grills – perfect for sunset feasts. Cinema, billiards, gym, air hockey, table tennis. Kayaks & SUPs await on your private shore. Boathouse: a sitting area above with a stunning view of the lake. Wake up to the gentle lapping of waves, sip coffee over glassy water... Unforgettable lake escapes start here.

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!

2,500 sq ft | Penthouse | Scotiabank Arena

Newly renovated Executive Penthouse — high-end comfort in Toronto's core. Perfect for business or leisure. → Steps from Convention Centre & Financial District → Next door to Scotiabank Arena → Around the corner from top restaurants & bars → Short walk to Harbourfront → Minutes to Rogers Centre, Ripley's & CN Tower ✔️ 3 KING beds ✔️ Motorized blackout blinds ✔️ 85" 4K TV + Sonos Arc Theatre ✔️ 10' floor-to-ceiling windows Luxury, location, and privacy — all in one.

Bayview Oasis: Luxe Lakeside Escape w/ Pickleball

Welcome to Bayview Oasis, our luxurious lake house on Georgian Bay. Enjoy breathtaking water views, a modern kitchen with high-end appliances, a cozy basement with a pool table and bar, and a master suite with top-notch amenities. Outdoors, relax in the cabana with a pizza oven, fireplace, picnic tables, spacious patio, hot tub, and our new custom pickleball court. Whether it's a romantic getaway or family vacation, Bayview Oasis is the perfect retreat.

Luxurious Lake House for Family Stays

Beautiful Lakehouse, 45 mins from Toronto, with Exquisite Lake Views. Luxurious Large home with high end finishes. Top of the line appliances. Work from home space from second floor loft. All the comforts and amenities you desire. Spa , featuring equipped gym, an infrared sauna and Hot tub. Games room which includes pool table ,air hockey and ping pong. Camp Fires, and Lawn games. Outdoor quiet time 10:00 pm. No parties allowed at this property.

The Robert House: Masterpiece in Harbord Village

The Robert House is a beautiful stylish home in the heart of the city. Located just south of the Annex neighbourhood, east of Toronto’s Little Italy and a stone’s throw from Kensington Market and Chinatown. Enjoy this remarkable home - steps to subway, landmarks, parks, markets, cafes, restaurants, bars & shops. You will remember your stay in this bright & spacious 3+1 bed, 2.5 bath with soaring 10 foot ceilings and high-end finishings.

Muskoka Luxury Cottage near Huntsville with Sauna

"Selena Lakehouse" is a gorgeous new modern build cottage on Buck Lake, about 25 minutes outside of Huntsville. Featuring 4 bedrooms, 2.5 washrooms, and an outdoor sauna, this serene property offers a great escape from the hustle and bustle of everyday life. Sleeps up to 10 (max 8 adults). Fully winterized year-round availability. Excellent location for access to many snowmobile trails. Outdoor wood-burning sauna.