diff --git a/homeassistant/components/ai_task/services.yaml b/homeassistant/components/ai_task/services.yaml
index 8a37990a5d7..1b018fe6a65 100644
--- a/homeassistant/components/ai_task/services.yaml
+++ b/homeassistant/components/ai_task/services.yaml
@@ -30,6 +30,7 @@ generate_data:
         media:
           accept:
             - "*"
+          multiple: true
 generate_image:
   fields:
     task_name:
@@ -57,3 +58,4 @@ generate_image:
         media:
           accept:
             - "*"
+          multiple: true
diff --git a/homeassistant/helpers/llm.py b/homeassistant/helpers/llm.py
index 900abb0b9c7..ab1a3dfa54c 100644
--- a/homeassistant/helpers/llm.py
+++ b/homeassistant/helpers/llm.py
@@ -782,9 +782,19 @@ def selector_serializer(schema: Any) -> Any:  # noqa: C901
             return {"type": "string", "enum": schema.config["languages"]}
         return {"type": "string", "format": "RFC 5646"}
 
-    if isinstance(schema, (selector.LocationSelector, selector.MediaSelector)):
+    if isinstance(schema, selector.LocationSelector):
         return convert(schema.DATA_SCHEMA)
 
+    if isinstance(schema, selector.MediaSelector):
+        item_schema = convert(schema.DATA_SCHEMA)
+        # Media selector allows multiple when configured
+        if schema.config.get("multiple"):
+            return {
+                "type": "array",
+                "items": item_schema,
+            }
+        return item_schema
+
     if isinstance(schema, selector.NumberSelector):
         result = {"type": "number"}
         if "min" in schema.config:
diff --git a/homeassistant/helpers/selector.py b/homeassistant/helpers/selector.py
index 215a15b3512..a3510726175 100644
--- a/homeassistant/helpers/selector.py
+++ b/homeassistant/helpers/selector.py
@@ -1030,6 +1030,7 @@ class MediaSelectorConfig(BaseSelectorConfig, total=False):
     """Class to represent a media selector config."""
 
     accept: list[str]
+    multiple: bool
 
 
 @SELECTORS.register("media")
@@ -1041,6 +1042,7 @@ class MediaSelector(Selector[MediaSelectorConfig]):
     CONFIG_SCHEMA = make_selector_config_schema(
         {
             vol.Optional("accept"): [str],
+            vol.Optional("multiple", default=False): cv.boolean,
         }
     )
     DATA_SCHEMA = vol.Schema(
@@ -1059,9 +1061,9 @@ class MediaSelector(Selector[MediaSelectorConfig]):
         """Instantiate a selector."""
         super().__init__(config)
 
-    def __call__(self, data: Any) -> dict[str, str]:
+    def __call__(self, data: Any) -> dict[str, str] | list[dict[str, str]]:
         """Validate the passed selection."""
-        schema = {
+        item_schema_dict = {
             key: value
             for key, value in self.DATA_SCHEMA.schema.items()
             if key != "entity_id"
@@ -1069,10 +1071,19 @@ class MediaSelector(Selector[MediaSelectorConfig]):
 
         if "accept" not in self.config:
             # If accept is not set, the entity_id field is required
-            schema[vol.Required("entity_id")] = cv.entity_id_or_uuid
+            item_schema_dict[vol.Required("entity_id")] = cv.entity_id_or_uuid
 
-        media: dict[str, str] = vol.Schema(schema)(data)
-        return media
+        item_schema = vol.Schema(item_schema_dict)
+
+        if not self.config["multiple"]:
+            media: dict[str, str] = item_schema(data)
+            return media
+
+        # Backwards compatibility for places that now accept multiple items
+        if not isinstance(data, list):
+            data = [data]
+
+        return [item_schema(item) for item in data]
 
 
 class NumberSelectorConfig(BaseSelectorConfig, total=False):
diff --git a/tests/helpers/test_llm.py b/tests/helpers/test_llm.py
index 7011ba42b72..7e237cc495e 100644
--- a/tests/helpers/test_llm.py
+++ b/tests/helpers/test_llm.py
@@ -1132,6 +1132,19 @@ async def test_selector_serializer(
         },
         "required": ["media_content_id", "media_content_type"],
     }
+    assert selector_serializer(selector.MediaSelector({"multiple": True})) == {
+        "type": "array",
+        "items": {
+            "type": "object",
+            "properties": {
+                "entity_id": {"type": "string"},
+                "media_content_id": {"type": "string"},
+                "media_content_type": {"type": "string"},
+                "metadata": {"type": "object", "additionalProperties": True},
+            },
+            "required": ["media_content_id", "media_content_type"],
+        },
+    }
     assert selector_serializer(selector.NumberSelector({"mode": "box"})) == {
         "type": "number"
     }
diff --git a/tests/helpers/test_selector.py b/tests/helpers/test_selector.py
index 73db8af126e..416701a1746 100644
--- a/tests/helpers/test_selector.py
+++ b/tests/helpers/test_selector.py
@@ -1164,6 +1164,8 @@ def test_media_selector_schema(schema, valid_selections, invalid_selections) ->
 
     def drop_metadata(data):
         """Drop metadata key from the input."""
+        if isinstance(data, list):
+            return [drop_metadata(item) for item in data]
         data.pop("metadata", None)
         return data
 
@@ -1176,6 +1178,96 @@ def test_media_selector_schema(schema, valid_selections, invalid_selections) ->
     )
 
 
+@pytest.mark.parametrize(
+    ("schema", "valid_selections", "invalid_selections"),
+    [
+        (
+            {"multiple": True},
+            (
+                [
+                    {
+                        "entity_id": "sensor.abc",
+                        "media_content_id": "abc",
+                        "media_content_type": "def",
+                    },
+                    {
+                        "entity_id": "sensor.def",
+                        "media_content_id": "ghi",
+                        "media_content_type": "jkl",
+                    },
+                ],
+                # Not a list is automatically converted to a list
+                {
+                    "entity_id": "sensor.abc",
+                    "media_content_id": "abc",
+                    "media_content_type": "def",
+                },
+            ),
+            (
+                None,
+                # Missing required key in one item
+                [
+                    {
+                        "entity_id": "sensor.abc",
+                        "media_content_id": "abc",
+                        "media_content_type": "def",
+                    },
+                    {
+                        "entity_id": "sensor.def",
+                        "media_content_id": "ghi",
+                    },
+                ],
+            ),
+        ),
+        (
+            {"multiple": True, "accept": ["image/*"]},
+            (
+                [
+                    {
+                        "media_content_id": "abc",
+                        "media_content_type": "def",
+                    },
+                    {
+                        "media_content_id": "ghi",
+                        "media_content_type": "jkl",
+                    },
+                ],
+            ),
+            (
+                None,
+                # entity_id not allowed when accept is set
+                [
+                    {
+                        "entity_id": "sensor.abc",
+                        "media_content_id": "abc",
+                        "media_content_type": "def",
+                    }
+                ],
+            ),
+        ),
+    ],
+)
+def test_media_selector_schema_multiple(
+    schema, valid_selections, invalid_selections
+) -> None:
+    """Test media selector with multiple selections."""
+
+    def drop_metadata(data, root=True):
+        if isinstance(data, list):
+            return [drop_metadata(item, False) for item in data]
+        data.pop("metadata", None)
+        # Multiple=true wraps single values in list.
+        return [data] if root and schema.get("multiple") else data
+
+    _test_selector(
+        "media",
+        schema,
+        valid_selections,
+        invalid_selections,
+        drop_metadata,
+    )
+
+
 @pytest.mark.parametrize(
     ("schema", "valid_selections", "invalid_selections"),
     [