diff --git a/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/cdk.out b/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/cdk.out
new file mode 100644
index 0000000000000..f0b901e7c06e5
--- /dev/null
+++ b/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/cdk.out
@@ -0,0 +1 @@
+{"version":"32.0.0"}
\ No newline at end of file
diff --git a/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/cdkintegs3bucketDefaultTestDeployAssertB89636B8.assets.json b/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/cdkintegs3bucketDefaultTestDeployAssertB89636B8.assets.json
new file mode 100644
index 0000000000000..09966cb17b39d
--- /dev/null
+++ b/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/cdkintegs3bucketDefaultTestDeployAssertB89636B8.assets.json
@@ -0,0 +1,19 @@
+{
+  "version": "32.0.0",
+  "files": {
+    "21fbb51d7b23f6a6c262b46a9caee79d744a3ac019fd45422d988b96d44b2a22": {
+      "source": {
+        "path": "cdkintegs3bucketDefaultTestDeployAssertB89636B8.template.json",
+        "packaging": "file"
+      },
+      "destinations": {
+        "current_account-current_region": {
+          "bucketName": "cdk-hnb659fds-assets-${AWS::AccountId}-${AWS::Region}",
+          "objectKey": "21fbb51d7b23f6a6c262b46a9caee79d744a3ac019fd45422d988b96d44b2a22.json",
+          "assumeRoleArn": "arn:${AWS::Partition}:iam::${AWS::AccountId}:role/cdk-hnb659fds-file-publishing-role-${AWS::AccountId}-${AWS::Region}"
+        }
+      }
+    }
+  },
+  "dockerImages": {}
+}
\ No newline at end of file
diff --git a/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/cdkintegs3bucketDefaultTestDeployAssertB89636B8.template.json b/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/cdkintegs3bucketDefaultTestDeployAssertB89636B8.template.json
new file mode 100644
index 0000000000000..ad9d0fb73d1dd
--- /dev/null
+++ b/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/cdkintegs3bucketDefaultTestDeployAssertB89636B8.template.json
@@ -0,0 +1,36 @@
+{
+ "Parameters": {
+  "BootstrapVersion": {
+   "Type": "AWS::SSM::Parameter::Value<String>",
+   "Default": "/cdk-bootstrap/hnb659fds/version",
+   "Description": "Version of the CDK Bootstrap resources in this environment, automatically retrieved from SSM Parameter Store. [cdk:skip]"
+  }
+ },
+ "Rules": {
+  "CheckBootstrapVersion": {
+   "Assertions": [
+    {
+     "Assert": {
+      "Fn::Not": [
+       {
+        "Fn::Contains": [
+         [
+          "1",
+          "2",
+          "3",
+          "4",
+          "5"
+         ],
+         {
+          "Ref": "BootstrapVersion"
+         }
+        ]
+       }
+      ]
+     },
+     "AssertDescription": "CDK bootstrap stack version 6 required. Please run 'cdk bootstrap' with a recent version of the CDK CLI."
+    }
+   ]
+  }
+ }
+}
\ No newline at end of file
diff --git a/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/integ.json b/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/integ.json
new file mode 100644
index 0000000000000..0a80e2e885375
--- /dev/null
+++ b/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/integ.json
@@ -0,0 +1,12 @@
+{
+  "version": "32.0.0",
+  "testCases": {
+    "cdk-integ-s3-bucket/DefaultTest": {
+      "stacks": [
+        "s3-bucket-routing"
+      ],
+      "assertionStack": "cdk-integ-s3-bucket/DefaultTest/DeployAssert",
+      "assertionStackName": "cdkintegs3bucketDefaultTestDeployAssertB89636B8"
+    }
+  }
+}
\ No newline at end of file
diff --git a/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/manifest.json b/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/manifest.json
new file mode 100644
index 0000000000000..940b94f176503
--- /dev/null
+++ b/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/manifest.json
@@ -0,0 +1,111 @@
+{
+  "version": "32.0.0",
+  "artifacts": {
+    "s3-bucket-routing.assets": {
+      "type": "cdk:asset-manifest",
+      "properties": {
+        "file": "s3-bucket-routing.assets.json",
+        "requiresBootstrapStackVersion": 6,
+        "bootstrapStackVersionSsmParameter": "/cdk-bootstrap/hnb659fds/version"
+      }
+    },
+    "s3-bucket-routing": {
+      "type": "aws:cloudformation:stack",
+      "environment": "aws://unknown-account/unknown-region",
+      "properties": {
+        "templateFile": "s3-bucket-routing.template.json",
+        "validateOnSynth": false,
+        "assumeRoleArn": "arn:${AWS::Partition}:iam::${AWS::AccountId}:role/cdk-hnb659fds-deploy-role-${AWS::AccountId}-${AWS::Region}",
+        "cloudFormationExecutionRoleArn": "arn:${AWS::Partition}:iam::${AWS::AccountId}:role/cdk-hnb659fds-cfn-exec-role-${AWS::AccountId}-${AWS::Region}",
+        "stackTemplateAssetObjectUrl": "s3://cdk-hnb659fds-assets-${AWS::AccountId}-${AWS::Region}/4c953dadd81493b9ba7f2a1c7b5aea35907c8e0df9be35cd5171c5d4393f5482.json",
+        "requiresBootstrapStackVersion": 6,
+        "bootstrapStackVersionSsmParameter": "/cdk-bootstrap/hnb659fds/version",
+        "additionalDependencies": [
+          "s3-bucket-routing.assets"
+        ],
+        "lookupRole": {
+          "arn": "arn:${AWS::Partition}:iam::${AWS::AccountId}:role/cdk-hnb659fds-lookup-role-${AWS::AccountId}-${AWS::Region}",
+          "requiresBootstrapStackVersion": 8,
+          "bootstrapStackVersionSsmParameter": "/cdk-bootstrap/hnb659fds/version"
+        }
+      },
+      "dependencies": [
+        "s3-bucket-routing.assets"
+      ],
+      "metadata": {
+        "/s3-bucket-routing/MyBucketWithRoutingRules/Resource": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "MyBucketWithRoutingRulesC6E1CAA2"
+          }
+        ],
+        "/s3-bucket-routing/BootstrapVersion": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "BootstrapVersion"
+          }
+        ],
+        "/s3-bucket-routing/CheckBootstrapVersion": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "CheckBootstrapVersion"
+          }
+        ]
+      },
+      "displayName": "s3-bucket-routing"
+    },
+    "cdkintegs3bucketDefaultTestDeployAssertB89636B8.assets": {
+      "type": "cdk:asset-manifest",
+      "properties": {
+        "file": "cdkintegs3bucketDefaultTestDeployAssertB89636B8.assets.json",
+        "requiresBootstrapStackVersion": 6,
+        "bootstrapStackVersionSsmParameter": "/cdk-bootstrap/hnb659fds/version"
+      }
+    },
+    "cdkintegs3bucketDefaultTestDeployAssertB89636B8": {
+      "type": "aws:cloudformation:stack",
+      "environment": "aws://unknown-account/unknown-region",
+      "properties": {
+        "templateFile": "cdkintegs3bucketDefaultTestDeployAssertB89636B8.template.json",
+        "validateOnSynth": false,
+        "assumeRoleArn": "arn:${AWS::Partition}:iam::${AWS::AccountId}:role/cdk-hnb659fds-deploy-role-${AWS::AccountId}-${AWS::Region}",
+        "cloudFormationExecutionRoleArn": "arn:${AWS::Partition}:iam::${AWS::AccountId}:role/cdk-hnb659fds-cfn-exec-role-${AWS::AccountId}-${AWS::Region}",
+        "stackTemplateAssetObjectUrl": "s3://cdk-hnb659fds-assets-${AWS::AccountId}-${AWS::Region}/21fbb51d7b23f6a6c262b46a9caee79d744a3ac019fd45422d988b96d44b2a22.json",
+        "requiresBootstrapStackVersion": 6,
+        "bootstrapStackVersionSsmParameter": "/cdk-bootstrap/hnb659fds/version",
+        "additionalDependencies": [
+          "cdkintegs3bucketDefaultTestDeployAssertB89636B8.assets"
+        ],
+        "lookupRole": {
+          "arn": "arn:${AWS::Partition}:iam::${AWS::AccountId}:role/cdk-hnb659fds-lookup-role-${AWS::AccountId}-${AWS::Region}",
+          "requiresBootstrapStackVersion": 8,
+          "bootstrapStackVersionSsmParameter": "/cdk-bootstrap/hnb659fds/version"
+        }
+      },
+      "dependencies": [
+        "cdkintegs3bucketDefaultTestDeployAssertB89636B8.assets"
+      ],
+      "metadata": {
+        "/cdk-integ-s3-bucket/DefaultTest/DeployAssert/BootstrapVersion": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "BootstrapVersion"
+          }
+        ],
+        "/cdk-integ-s3-bucket/DefaultTest/DeployAssert/CheckBootstrapVersion": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "CheckBootstrapVersion"
+          }
+        ]
+      },
+      "displayName": "cdk-integ-s3-bucket/DefaultTest/DeployAssert"
+    },
+    "Tree": {
+      "type": "cdk:tree",
+      "properties": {
+        "file": "tree.json"
+      }
+    }
+  }
+}
\ No newline at end of file
diff --git a/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/s3-bucket-routing.assets.json b/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/s3-bucket-routing.assets.json
new file mode 100644
index 0000000000000..d429f99eb00e3
--- /dev/null
+++ b/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/s3-bucket-routing.assets.json
@@ -0,0 +1,19 @@
+{
+  "version": "32.0.0",
+  "files": {
+    "4c953dadd81493b9ba7f2a1c7b5aea35907c8e0df9be35cd5171c5d4393f5482": {
+      "source": {
+        "path": "s3-bucket-routing.template.json",
+        "packaging": "file"
+      },
+      "destinations": {
+        "current_account-current_region": {
+          "bucketName": "cdk-hnb659fds-assets-${AWS::AccountId}-${AWS::Region}",
+          "objectKey": "4c953dadd81493b9ba7f2a1c7b5aea35907c8e0df9be35cd5171c5d4393f5482.json",
+          "assumeRoleArn": "arn:${AWS::Partition}:iam::${AWS::AccountId}:role/cdk-hnb659fds-file-publishing-role-${AWS::AccountId}-${AWS::Region}"
+        }
+      }
+    }
+  },
+  "dockerImages": {}
+}
\ No newline at end of file
diff --git a/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/s3-bucket-routing.template.json b/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/s3-bucket-routing.template.json
new file mode 100644
index 0000000000000..1f15e8e9a5c9f
--- /dev/null
+++ b/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/s3-bucket-routing.template.json
@@ -0,0 +1,60 @@
+{
+ "Resources": {
+  "MyBucketWithRoutingRulesC6E1CAA2": {
+   "Type": "AWS::S3::Bucket",
+   "Properties": {
+    "WebsiteConfiguration": {
+     "IndexDocument": "index.html",
+     "RoutingRules": [
+      {
+       "RedirectRule": {
+        "HostName": "example.com",
+        "Protocol": "https",
+        "ReplaceKeyWith": "/"
+       },
+       "RoutingRuleCondition": {
+        "KeyPrefixEquals": ""
+       }
+      }
+     ]
+    }
+   },
+   "UpdateReplacePolicy": "Delete",
+   "DeletionPolicy": "Delete"
+  }
+ },
+ "Parameters": {
+  "BootstrapVersion": {
+   "Type": "AWS::SSM::Parameter::Value<String>",
+   "Default": "/cdk-bootstrap/hnb659fds/version",
+   "Description": "Version of the CDK Bootstrap resources in this environment, automatically retrieved from SSM Parameter Store. [cdk:skip]"
+  }
+ },
+ "Rules": {
+  "CheckBootstrapVersion": {
+   "Assertions": [
+    {
+     "Assert": {
+      "Fn::Not": [
+       {
+        "Fn::Contains": [
+         [
+          "1",
+          "2",
+          "3",
+          "4",
+          "5"
+         ],
+         {
+          "Ref": "BootstrapVersion"
+         }
+        ]
+       }
+      ]
+     },
+     "AssertDescription": "CDK bootstrap stack version 6 required. Please run 'cdk bootstrap' with a recent version of the CDK CLI."
+    }
+   ]
+  }
+ }
+}
\ No newline at end of file
diff --git a/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/tree.json b/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/tree.json
new file mode 100644
index 0000000000000..d2a695b2395d7
--- /dev/null
+++ b/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.js.snapshot/tree.json
@@ -0,0 +1,139 @@
+{
+  "version": "tree-0.1",
+  "tree": {
+    "id": "App",
+    "path": "",
+    "children": {
+      "s3-bucket-routing": {
+        "id": "s3-bucket-routing",
+        "path": "s3-bucket-routing",
+        "children": {
+          "MyBucketWithRoutingRules": {
+            "id": "MyBucketWithRoutingRules",
+            "path": "s3-bucket-routing/MyBucketWithRoutingRules",
+            "children": {
+              "Resource": {
+                "id": "Resource",
+                "path": "s3-bucket-routing/MyBucketWithRoutingRules/Resource",
+                "attributes": {
+                  "aws:cdk:cloudformation:type": "AWS::S3::Bucket",
+                  "aws:cdk:cloudformation:props": {
+                    "websiteConfiguration": {
+                      "indexDocument": "index.html",
+                      "routingRules": [
+                        {
+                          "redirectRule": {
+                            "hostName": "example.com",
+                            "protocol": "https",
+                            "replaceKeyWith": "/"
+                          },
+                          "routingRuleCondition": {
+                            "keyPrefixEquals": ""
+                          }
+                        }
+                      ]
+                    }
+                  }
+                },
+                "constructInfo": {
+                  "fqn": "aws-cdk-lib.aws_s3.CfnBucket",
+                  "version": "0.0.0"
+                }
+              }
+            },
+            "constructInfo": {
+              "fqn": "aws-cdk-lib.aws_s3.Bucket",
+              "version": "0.0.0"
+            }
+          },
+          "BootstrapVersion": {
+            "id": "BootstrapVersion",
+            "path": "s3-bucket-routing/BootstrapVersion",
+            "constructInfo": {
+              "fqn": "aws-cdk-lib.CfnParameter",
+              "version": "0.0.0"
+            }
+          },
+          "CheckBootstrapVersion": {
+            "id": "CheckBootstrapVersion",
+            "path": "s3-bucket-routing/CheckBootstrapVersion",
+            "constructInfo": {
+              "fqn": "aws-cdk-lib.CfnRule",
+              "version": "0.0.0"
+            }
+          }
+        },
+        "constructInfo": {
+          "fqn": "aws-cdk-lib.Stack",
+          "version": "0.0.0"
+        }
+      },
+      "cdk-integ-s3-bucket": {
+        "id": "cdk-integ-s3-bucket",
+        "path": "cdk-integ-s3-bucket",
+        "children": {
+          "DefaultTest": {
+            "id": "DefaultTest",
+            "path": "cdk-integ-s3-bucket/DefaultTest",
+            "children": {
+              "Default": {
+                "id": "Default",
+                "path": "cdk-integ-s3-bucket/DefaultTest/Default",
+                "constructInfo": {
+                  "fqn": "constructs.Construct",
+                  "version": "10.2.55"
+                }
+              },
+              "DeployAssert": {
+                "id": "DeployAssert",
+                "path": "cdk-integ-s3-bucket/DefaultTest/DeployAssert",
+                "children": {
+                  "BootstrapVersion": {
+                    "id": "BootstrapVersion",
+                    "path": "cdk-integ-s3-bucket/DefaultTest/DeployAssert/BootstrapVersion",
+                    "constructInfo": {
+                      "fqn": "aws-cdk-lib.CfnParameter",
+                      "version": "0.0.0"
+                    }
+                  },
+                  "CheckBootstrapVersion": {
+                    "id": "CheckBootstrapVersion",
+                    "path": "cdk-integ-s3-bucket/DefaultTest/DeployAssert/CheckBootstrapVersion",
+                    "constructInfo": {
+                      "fqn": "aws-cdk-lib.CfnRule",
+                      "version": "0.0.0"
+                    }
+                  }
+                },
+                "constructInfo": {
+                  "fqn": "aws-cdk-lib.Stack",
+                  "version": "0.0.0"
+                }
+              }
+            },
+            "constructInfo": {
+              "fqn": "@aws-cdk/integ-tests-alpha.IntegTestCase",
+              "version": "0.0.0"
+            }
+          }
+        },
+        "constructInfo": {
+          "fqn": "@aws-cdk/integ-tests-alpha.IntegTest",
+          "version": "0.0.0"
+        }
+      },
+      "Tree": {
+        "id": "Tree",
+        "path": "Tree",
+        "constructInfo": {
+          "fqn": "constructs.Construct",
+          "version": "10.2.55"
+        }
+      }
+    },
+    "constructInfo": {
+      "fqn": "aws-cdk-lib.App",
+      "version": "0.0.0"
+    }
+  }
+}
\ No newline at end of file
diff --git a/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.ts b/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.ts
new file mode 100644
index 0000000000000..4f0ffc8054b4f
--- /dev/null
+++ b/packages/@aws-cdk-testing/framework-integ/test/aws-s3/test/integ.bucket.website-routing-rules.ts
@@ -0,0 +1,23 @@
+#!/usr/bin/env node
+import * as cdk from 'aws-cdk-lib';
+import { IntegTest } from '@aws-cdk/integ-tests-alpha';
+import * as s3 from 'aws-cdk-lib/aws-s3';
+
+const app = new cdk.App();
+
+const stack = new cdk.Stack(app, 's3-bucket-routing');
+
+new s3.Bucket(stack, 'MyBucketWithRoutingRules', {
+  removalPolicy: cdk.RemovalPolicy.DESTROY,
+  websiteIndexDocument: 'index.html',
+  websiteRoutingRules: [{
+    condition: { keyPrefixEquals: '' },
+    hostName: 'example.com',
+    protocol: s3.RedirectProtocol.HTTPS,
+    replaceKey: s3.ReplaceKey.with('/'),
+  }],
+});
+
+new IntegTest(app, 'cdk-integ-s3-bucket', {
+  testCases: [stack],
+});
diff --git a/packages/aws-cdk-lib/aws-s3/lib/bucket.ts b/packages/aws-cdk-lib/aws-s3/lib/bucket.ts
index 3eb7cfce25a78..6812e73bb0af5 100644
--- a/packages/aws-cdk-lib/aws-s3/lib/bucket.ts
+++ b/packages/aws-cdk-lib/aws-s3/lib/bucket.ts
@@ -2318,7 +2318,7 @@ export class Bucket extends BucketBase {
     }
 
     const routingRules = props.websiteRoutingRules ? props.websiteRoutingRules.map<CfnBucket.RoutingRuleProperty>((rule) => {
-      if (rule.condition && !rule.condition.httpErrorCodeReturnedEquals && !rule.condition.keyPrefixEquals) {
+      if (rule.condition && rule.condition.httpErrorCodeReturnedEquals == null && rule.condition.keyPrefixEquals == null) {
         throw new Error('The condition property cannot be an empty object');
       }
 
diff --git a/packages/aws-cdk-lib/aws-s3/test/bucket.test.ts b/packages/aws-cdk-lib/aws-s3/test/bucket.test.ts
index 1eef08ff7ad8b..7f7b672f5df00 100644
--- a/packages/aws-cdk-lib/aws-s3/test/bucket.test.ts
+++ b/packages/aws-cdk-lib/aws-s3/test/bucket.test.ts
@@ -2592,6 +2592,38 @@ describe('bucket', () => {
         },
       });
 
+    });
+    test('adds RedirectRules property with empty keyPrefixEquals condition', () => {
+      const stack = new cdk.Stack();
+      new s3.Bucket(stack, 'Website', {
+        websiteRoutingRules: [{
+          hostName: 'www.example.com',
+          httpRedirectCode: '302',
+          protocol: s3.RedirectProtocol.HTTPS,
+          replaceKey: s3.ReplaceKey.prefixWith('test/'),
+          condition: {
+            httpErrorCodeReturnedEquals: '200',
+            keyPrefixEquals: '',
+          },
+        }],
+      });
+      Template.fromStack(stack).hasResourceProperties('AWS::S3::Bucket', {
+        WebsiteConfiguration: {
+          RoutingRules: [{
+            RedirectRule: {
+              HostName: 'www.example.com',
+              HttpRedirectCode: '302',
+              Protocol: 'https',
+              ReplaceKeyPrefixWith: 'test/',
+            },
+            RoutingRuleCondition: {
+              HttpErrorCodeReturnedEquals: '200',
+              KeyPrefixEquals: '',
+            },
+          }],
+        },
+      });
+
     });
     test('fails if routingRule condition object is empty', () => {
       const stack = new cdk.Stack();