Background/Objectives: An adapted version of an online pictorial food frequency questionnaire (FFQ), VioScreen-Allergy, assesses total dietary intake and intake of allergens and foods in the maternal diet index (MDI), linked to offspring allergy. This study assessed intermethod reliability, test–retest reliability, and external validity of the VioScreen-Allergy. Methods: Females of childbearing age were recruited at Denver Health and Children’s Hospital, Colorado, USA, and were asked to complete four 24 h recalls and two VioScreen-Allergy FFQs over the course of a month. All those with at least two 24 h dietary recalls and both VioScreen-Allergy assessments were analyzed. Energy-adjusted and non-adjusted linear mixed models (1) compared MDI scores and intake of nutrients and allergens as measures of intermethod reliability; (2) evaluated VioScreen-Allergy test–retest reliability as differences between repeated measurements; and (3) assessed external validity by modeling associations between VioScreen-Allergy-derived intake of beta-carotene and orange vegetables and Veggie Meter®-assessed skin carotenoids. Bonferroni corrections controlled multiple comparisons within the assessment. Results: Of 53 participants enrolled, 25 demographically dissimilar participants were included in the analysis. There were no significant differences between 24 h recall and VioScreen-Allergy mean intakes of macronutrients, micronutrients, allergens, or MDI, except for Vitamin C, niacin, and cashew allergen protein. There were no significant differences between repeated measurements of VioScreen-Allergy, either energy-adjusted or unadjusted. Both beta-carotene and orange vegetable servings were significantly associated with Veggie Meter®. Conclusions: Although non-significance could have been due to low power, clinical as well as statistical assessments of intermethod reliability, test–retest reliability, and external validity suggest that VioScreen-Allergy has reasonable utility for trials assessing food allergens and MDI in the context of overall intake. The VioScreen questionnaire can also be used in future studies to assess macro- and micronutrient intake. Additional validation studies assessing different portion sizes and foods eaten by infants and young children are currently undergoing.