Callaway sits next to 4 phonetic neighbors — Calloway, Callie, and Holloway are the closest matches by sound. Most share Callaway's English-origin cluster, so the rhythm and vowel shape carry across the list.
You searched for names like
"pebbly place"
"lily (pure, white flower)"
"free woman"
"rival, striving"
"who is like God"
"dweller near the oak trees"
"delight, bliss"
"culture, cultivation of society"
"brave lion"
"of the Aelian family"
"the great one, exhilarating"
"modern invented name, blue jay bird"
"evening, twilight"
"true, authentic, loyal"
"invented/unique"
"envious (alternative etymology)"
"from Lassy, Norman place name"
"star-shaped flower"
"sword"
"noble kind"
"uncertain — possibly Native American origin"
Similar sound: These names share phonetic patterns with Callaway — similar vowel sounds, consonant clusters, or rhythm.
Shared roots: Several names on this list have Old French origins, giving them the same cultural heritage as Callaway.
Rhythm: Callaway is a 3-syllable name. Names with the same syllable count tend to feel interchangeable when you're narrowing your list.