[2] In the peasant family from the Haavakivi mill-farm, Anna was raised with her older sister, Elisabet (1860–1893), and a younger brother, Rudolf (1870s–1950).

[1][2] Haava's fluency with languages helped her throughout her life because the history of Estonia included, in turn, periods of Tsarist-Russian influence, new national independence, occupation by German forces during World War II, and annexation into the USSR by Soviet Russia.

[3] While Haava attended the German-language school, she was given a "more German-sounding" name, Anna Rosalie Espenstein, and taught how to be a good German.

[1][2] Haava's first three collections, Luuletused I (Poems I) (1888), II (1890) and III (1897) contain romantic sentimental songs, the main theme of which is love.

Haava wrote to condemn injustice, violence and ethnic discrimination, and her criticism only deepened in some poetry collections, Ristlained (Crosswaves, 1910) and Meie päevist (From Our Days, 1920).

Haava's poetry became even more personal in the collections Põhjamaa lapsed (Children of the Nordic countries, 1913), Siiski on elu ilus (Still, Life is Beautiful), and Laulan oma eesti laulu (I Sing My Estonian Song, 1935).

Goethe's Egmont, F. Schiller's Wilhelm Tell, H. Hofmannstahl's King Oedipus, W. Shakespeare's A Midsummer Night's Dream and Hans Christian Andersen's fairy tales, among others.

[1][2] Her own poems were widely translated, including Russian, Finnish, Swedish, Hungarian, German, Italian, Esperanto, English and other languages as well.

[2][6] As a young woman, Anna started singing in a folk choir and fell in love with a student of the theological faculty of the University of Tartu.

[2] Her personal life in pieces, she traveled to Leipzig, Germany for her health, and then moved for several years to St. Petersburg, Russia where she became a nurse and teacher.