diff --git a/packages/vite/src/node/plugins/html.ts b/packages/vite/src/node/plugins/html.ts
index cb9bf87192258d..537f58470a9cbd 100644
--- a/packages/vite/src/node/plugins/html.ts
+++ b/packages/vite/src/node/plugins/html.ts
@@ -717,7 +717,7 @@ export function buildHtmlPlugin(config: ResolvedConfig): Plugin {
     },
 
     async generateBundle(options, bundle) {
-      const analyzedChunk = new Map<OutputChunk, number>()
+      const analyzedImportedCssFiles = new Map<OutputChunk, string[]>()
       const inlineEntryChunk = new Set<string>()
       const getImportedChunks = (
         chunk: OutputChunk,
@@ -777,39 +777,62 @@ export function buildHtmlPlugin(config: ResolvedConfig): Plugin {
         },
       })
 
-      const getCssTagsForChunk = (
-        chunk: OutputChunk,
+      const toStyleSheetLinkTag = (
+        file: string,
         toOutputPath: (filename: string) => string,
-        seen: Set<string> = new Set(),
-      ): HtmlTagDescriptor[] => {
-        const tags: HtmlTagDescriptor[] = []
-        if (!analyzedChunk.has(chunk)) {
-          analyzedChunk.set(chunk, 1)
-          chunk.imports.forEach((file) => {
-            const importee = bundle[file]
-            if (importee?.type === 'chunk') {
-              tags.push(...getCssTagsForChunk(importee, toOutputPath, seen))
-            }
-          })
+      ): HtmlTagDescriptor => ({
+        tag: 'link',
+        attrs: {
+          rel: 'stylesheet',
+          crossorigin: true,
+          href: toOutputPath(file),
+        },
+      })
+
+      const getCssFilesForChunk = (
+        chunk: OutputChunk,
+        seenChunks: Set<string> = new Set(),
+        seenCss: Set<string> = new Set(),
+      ): string[] => {
+        if (seenChunks.has(chunk.fileName)) {
+          return []
+        }
+        seenChunks.add(chunk.fileName)
+
+        if (analyzedImportedCssFiles.has(chunk)) {
+          const files = analyzedImportedCssFiles.get(chunk)!
+          const additionals = files.filter((file) => !seenCss.has(file))
+          additionals.forEach((file) => seenCss.add(file))
+          return additionals
         }
 
+        const files: string[] = []
+        chunk.imports.forEach((file) => {
+          const importee = bundle[file]
+          if (importee?.type === 'chunk') {
+            files.push(...getCssFilesForChunk(importee, seenChunks, seenCss))
+          }
+        })
+        analyzedImportedCssFiles.set(chunk, files)
+
         chunk.viteMetadata!.importedCss.forEach((file) => {
-          if (!seen.has(file)) {
-            seen.add(file)
-            tags.push({
-              tag: 'link',
-              attrs: {
-                rel: 'stylesheet',
-                crossorigin: true,
-                href: toOutputPath(file),
-              },
-            })
+          if (!seenCss.has(file)) {
+            seenCss.add(file)
+            files.push(file)
           }
         })
 
-        return tags
+        return files
       }
 
+      const getCssTagsForChunk = (
+        chunk: OutputChunk,
+        toOutputPath: (filename: string) => string,
+      ) =>
+        getCssFilesForChunk(chunk).map((file) =>
+          toStyleSheetLinkTag(file, toOutputPath),
+        )
+
       for (const [normalizedId, html] of processedHtml(this)) {
         const relativeUrlPath = normalizePath(
           path.relative(config.root, normalizedId),