While a young architect working for his father, Sharp designed a motel for a family friend; its success motivated him to try creating his own hotel.

He bought a large parcel of land in a run-down area of Toronto and planned a stopover for business travelers; the Four Seasons Motor Hotel opened in 1961 with initial investors, Murray Koffler, Fred Eisen, and Eddie Creed.

As a result, the company began shifting to its current, management-only business model, eliminating costs associated with buying land and buildings.

[5] The company recovered, and in 2007 it agreed to a buyout by Microsoft Chairman Bill Gates and Prince Al-Waleed bin Talal of Saudi Arabia for $3.8 billion.

[5] During the Great Recession, the company made the first corporate layoffs in its history, cutting 10% of its Toronto workforce.

[5] In April 2010, after a year-long dispute with Broadreach Capital Partners and Maritz, Wolff & Co., owners of the Aviara resort near San Diego, an arbitration panel ruled that, while both parties contributed to the demise of the business relationship, Four Seasons had not violated its management agreement.

[23] The penthouse was bought by entrepreneur Robert Österlund (founder of Xacti, LLC and Inbox.com) for a Canadian record price of over $28 million.

Property owners are required to additionally contribute money for marketing, chain-wide sales, reservations systems and renovations.

Profit margins are relatively low, but the brand attracts developers through the hotels' reputation as solid assets for loan collateral or resale.

Titled Residential Rentals, the properties are available in: North America (Costa Rica, Houston, Jackson Hole, Nevis, Punta Mita, San Diego, Whistler, Vail).

Africa (Marrakech, Mauritius, Seychelles, Sharm El Sheikh), Europe (Cap-Ferrat) and Asia (Bali at Jimbaran Bay, Jakarta, Chiang Mai, Koh Samui, Bangkok).

Visitors from the Maldives' two Four Seasons resorts, Kuda Huraa and Landaa Giraavaru, could either book rooms or charter the entire ship for trips that lasted from three to seven days.

[188] After two decades, the ship left the Maldives in 2023 for Palau, where Four Seasons began offering tours at the end of that year.

[190] The first ultra luxury super yacht "Four Seasons I" was floated in Fincantieri Shipyard, Italy in January, 2025.

[192][193] Readers of Conde Nast Traveler magazine have voted Four Seasons Tented Camp Golden Triangle in Chiang Rai, Thailand as among the top ten hotels in the world for three consecutive years.