Such deals would normally be prohibited under the U.S. economic embargo of Cuba, but Starwood received special permission from the U.S. 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 U.S. company to commit major money to Cuba since Fidel Castro and his bearded rebels overthrew a pro-American government on Jan. 1, 1959.
Castro quickly nationalized the tourism industry and made the Habana Hilton the new government headquarters for months.
Cuba's tourism industry has boomed since the December 2014 rapprochement with the United States. International visitors rose 17 percent to a record 3.5 million in 2015, including a 77 percent increase in American visitors to 161,000.
Cuba expects a similar increase in American visitors this year when scheduled airline service will resume despite a continued ban on tourism. Americans are allowed to travel to Cuba for 12 authorized purposes.