diff --git a/openapi_core/templating/paths/finders.py b/openapi_core/templating/paths/finders.py
index bc90d45b..394ce190 100644
--- a/openapi_core/templating/paths/finders.py
+++ b/openapi_core/templating/paths/finders.py
@@ -39,8 +39,9 @@ def find(self, request):
             raise ServerNotFound(request.full_url_pattern)
 
     def _get_paths_iter(self, full_url_pattern):
+        template_paths = []
         for path_pattern, path in iteritems(self.spec.paths):
-            # simple path
+            # simple path. Return right away since it is always the most concrete
             if full_url_pattern.endswith(path_pattern):
                 path_result = TemplateResult(path_pattern, {})
                 yield (path, path_result)
@@ -49,7 +50,11 @@ def _get_paths_iter(self, full_url_pattern):
                 result = search(path_pattern, full_url_pattern)
                 if result:
                     path_result = TemplateResult(path_pattern, result.named)
-                    yield (path, path_result)
+                    template_paths.append((path, path_result))
+
+        # Fewer variables -> more concrete path
+        for path in sorted(template_paths, key=lambda p: len(p[1].variables)):
+            yield path
 
     def _get_operations_iter(self, request_method, paths_iter):
         for path, path_result in paths_iter:
diff --git a/tests/unit/templating/test_paths_finders.py b/tests/unit/templating/test_paths_finders.py
index 953cc1e7..3b95aa0d 100644
--- a/tests/unit/templating/test_paths_finders.py
+++ b/tests/unit/templating/test_paths_finders.py
@@ -435,3 +435,90 @@ def test_valid(self, finder, path_2, operation_2, server):
         assert result == (
             path_2, operation_2, server, path_result, server_result,
         )
+
+
+class TestConcretePaths(
+        BaseTestSpecServer, BaseTestSimpleServer):
+
+    path_name = '/keys/{id}/tokens'
+
+    @pytest.fixture
+    def operation_2(self):
+        return Operation('get', '/keys/master/tokens', {}, {})
+
+    @pytest.fixture
+    def operations_2(self, operation_2):
+        return {
+            'get': operation_2,
+        }
+
+    @pytest.fixture
+    def path(self, operations):
+        return Path('/keys/{id}/tokens', operations)
+
+    @pytest.fixture
+    def path_2(self, operations_2):
+        return Path('/keys/master/tokens', operations_2)
+
+    @pytest.fixture
+    def paths(self, path, path_2):
+        return {
+            path.name: path,
+            path_2.name: path_2,
+        }
+
+    def test_valid(self, finder, path_2, operation_2, server):
+        request_uri = '/keys/master/tokens'
+        request = MockRequest(
+            'http://petstore.swagger.io', 'get', request_uri)
+        result = finder.find(request)
+
+        path_result = TemplateResult(path_2.name, {})
+        server_result = TemplateResult(self.server_url, {})
+        assert result == (
+            path_2, operation_2, server, path_result, server_result,
+        )
+
+
+class TestTemplateConcretePaths(
+        BaseTestSpecServer, BaseTestSimpleServer):
+
+    path_name = '/keys/{id}/tokens/{id2}'
+
+    @pytest.fixture
+    def operation_2(self):
+        return Operation('get', '/keys/{id}/tokens/master', {}, {})
+
+    @pytest.fixture
+    def operations_2(self, operation_2):
+        return {
+            'get': operation_2,
+        }
+
+    @pytest.fixture
+    def path(self, operations):
+        return Path('/keys/{id}/tokens/{id2}', operations)
+
+    @pytest.fixture
+    def path_2(self, operations_2):
+        return Path('/keys/{id}/tokens/master', operations_2)
+
+    @pytest.fixture
+    def paths(self, path, path_2):
+        return {
+            path.name: path,
+            path_2.name: path_2,
+        }
+
+    def test_valid(self, finder, path_2, operation_2, server):
+        token_id = '123'
+        request_uri = '/keys/{0}/tokens/master'.format(token_id)
+        request = MockRequest(
+            'http://petstore.swagger.io', 'get', request_uri)
+        result = finder.find(request)
+
+        path_result = TemplateResult(path_2.name, {'id': '123'})
+        server_result = TemplateResult(self.server_url, {})
+        assert result == (
+            path_2, operation_2, server, path_result, server_result,
+        )