In a small saucepan over medium heat, add strawberries, sugar and water. Bring to a boil, then reduce heat and simmer for 3 to 5 minutes, until strawberries are soft.
Remove from heat and let cool, then strain berries into a bowl. Use a spatula to extract as much juice from the strawberries as possible. Whisk vanilla extract into strawberries.
Place two martini glasses in the freezer for 5 minutes. Meanwhile, melt chocolate in a small saucepan over low heat. Remove glasses from freezer and use a spoon to drizzle chocolate on insides of glasses. Let harden.
In a cocktail shaker filled halfway with ice, add Irish cream liqueur, vodka and strawberry syrup. Shake well for 10 seconds, then strain into cocktail glasses. Garnish with a strawberry heart. Enjoy!