It boasted 630 guest rooms, including 42 suites; an elegant casino; six restaurants and bars, including a Trader Vic's and a rooftop bar; a huge supper club; extensive convention facilities; a shopping arcade; an outdoor pool surrounded by cabanas; and two underground garages with a capacity of 500 cars.

[12] A formal blessing ceremony was held in the hotel's lobby on March 22, 1958, attended by Cuba's First Lady, Marta Fernandez de Batista; Francisco Aguirre, head of the catering workers' union; José Suárez Rivas, Minister of Labor; and other dignitaries.

Roberto Mendoza was a wealthy Cuban contractor and sugar planter who was a business associate of President Batista; Mario Mendoza was a lawyer; Orseck was an attorney from New York; Johnson was a senator in the Nevada state legislature and Jones was a former lieutenant governor of Nevada who had ownership interests in a number of Las Vegas casinos.

Speculation surfaced that the murder of Gambino crime family boss Albert Anastasia in October 1957 was tied to his interest in securing an ownership stake in the Hilton's casino.

"[22] On June 21, 1959,[24] the revolutionary government temporarily released mob boss Santo Trafficante Jr. from the Triscornia prison camp, under guard, so he could attend the wedding of his daughter Mary Jo in the ballroom of the Habana Hilton.

[25] In October 1959, the Habana Hilton hosted the week-long American Society of Travel Agents annual international convention,[26] which had been scheduled before the Revolution.

Castro and other officials attempted to present an image of Cuba as a continued tropical paradise for American tourists, as the country desperately needed the revenue, but growing anti-American political rhetoric was already having an impact on bookings at the increasingly empty hotel.

[26] On New Year's Eve 1959/1960, Castro hosted an elaborate party in the Pavilion ballroom atop the hotel, designed to promote Cuba to Americans.

Castro's American mistress, Marita Lorenz, had lived with him in the hotel for much of 1959, before returning to the United States, allegedly after an abortion.

Lorenz said she had a change of heart on returning to the hotel, only to then discover that the plan was a failure, as the pills had dissolved in the container of cold cream she had hidden them in.

From October 23 to November 20, 1966, the Habana Libre hosted the 17th Chess Olympiad, with guests including Bobby Fischer and Boris Spassky.

In January 1998, the hotel served as the international media headquarters for the Papal visit to Cuba by Pope John Paul II.

[43] Journalists including Peter Jennings, Dan Rather, Ted Koppel, Tom Brokaw and Christiane Amanpour reported from and were housed at the hotel.