Starwood Hotels & Resorts is the first American hotel company to sign a deal with Cuba since the 1959 revolution.
The company, which is already involved in a $13.6 billion takeover bid from Marriott, announced a multimillion-dollar investment.
Under the deal Starwood will manage and market two properties in Havana and signed a letter of intent to operate a third, it said on Saturday.
Deals like this are still prohibited under the US economic embargo of Cuba, but Starwood received special permission from the US Treasury Department last week.
Jorge Giannattasio, chief of Latin American operations, said the deals included a “multimillion-dollar investment to bring the hotels up to our standards,” making Starwood the first US company to commit major money to Cuba since it lost its pro-American government on January 1, 1959.
The Starwood investment comes at a time when international visits have increased by 17% in less than two years. More than 3.5 million travelers visited Cuba in 2015.
Obama has called for Congress to do away with the 54-year-old embargo but he has been opposed by the leadership of the Republican majority.
Starwood will operate the military-owned Gaviota 5th Avenue Hotel under its Four Points Sheraton brand, and the state-owned Gran Caribe Inglaterra Hotel under its Luxury Collection brand.