diff --git a/CHANGELOG.md b/CHANGELOG.md
index 8a22cda7e957f..2e39a51694931 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -282,6 +282,9 @@ The format is based on [Keep a Changelog](http://keepachangelog.com/en/1.0.0/).
 - Deprecated the `Trainer.train_loop` property in favor of `Trainer.fit_loop` ([#8025](https://github.com/PyTorchLightning/pytorch-lightning/pull/8025))
 
 
+- Deprecated the `Trainer.disable_validation` property in favor of `not Trainer.enable_validation` ([#8291](https://github.com/PyTorchLightning/pytorch-lightning/pull/8291))
+
+
 - Deprecated `mode` parameter in `ModelSummary` in favor of `max_depth` ([#8062](https://github.com/PyTorchLightning/pytorch-lightning/pull/8062))
 
 
diff --git a/pytorch_lightning/loops/fit_loop.py b/pytorch_lightning/loops/fit_loop.py
index f4fa04070a961..555b9bf6b76a3 100644
--- a/pytorch_lightning/loops/fit_loop.py
+++ b/pytorch_lightning/loops/fit_loop.py
@@ -235,7 +235,7 @@ def on_advance_end(self) -> None:
 
         self.epoch_loop.update_lr_schedulers('epoch', update_plateau_schedulers=True)
 
-        did_train_only = self.trainer.disable_validation or self.epoch_loop.val_loop.skip
+        did_train_only = not self.trainer.enable_validation or self.epoch_loop.val_loop.skip
         if did_train_only:
             self.global_step -= 1
             self._check_checkpoint_callback(True)
diff --git a/pytorch_lightning/trainer/properties.py b/pytorch_lightning/trainer/properties.py
index f57110368ef2e..a519b82234a43 100644
--- a/pytorch_lightning/trainer/properties.py
+++ b/pytorch_lightning/trainer/properties.py
@@ -38,7 +38,7 @@
 from pytorch_lightning.trainer.connectors.logger_connector import LoggerConnector
 from pytorch_lightning.trainer.connectors.logger_connector.result import ResultCollection
 from pytorch_lightning.trainer.states import RunningStage, TrainerFn, TrainerState, TrainerStatus
-from pytorch_lightning.utilities import DeviceType, DistributedType, rank_zero_warn
+from pytorch_lightning.utilities import DeviceType, DistributedType, rank_zero_deprecation, rank_zero_warn
 from pytorch_lightning.utilities.argparse import (
     add_argparse_args,
     from_argparse_args,
@@ -296,6 +296,10 @@ def progress_bar_dict(self) -> dict:
     @property
     def disable_validation(self) -> bool:
         """ Check if validation is disabled during training. """
+        rank_zero_deprecation(
+            "`trainer.disable_validation` is deprecated in v1.4 and will be removed in v1.6."
+            " Use `not trainer.enable_validation` instead."
+        )
         return not self.enable_validation
 
     @property
diff --git a/tests/deprecated_api/test_remove_1-6.py b/tests/deprecated_api/test_remove_1-6.py
index ba033a0ebeced..ac5b56ea00086 100644
--- a/tests/deprecated_api/test_remove_1-6.py
+++ b/tests/deprecated_api/test_remove_1-6.py
@@ -275,3 +275,9 @@ def test_v1_6_0_deprecated_model_summary_mode(tmpdir):
 
     with pytest.deprecated_call(match="Argument `mode` in `LightningModule.summarize` is deprecated in v1.4"):
         model.summarize(mode="top")
+
+
+def test_v1_6_0_deprecated_disable_validation():
+    trainer = Trainer()
+    with pytest.deprecated_call(match="disable_validation` is deprecated in v1.4"):
+        _ = trainer.disable_validation
diff --git a/tests/trainer/test_dataloaders.py b/tests/trainer/test_dataloaders.py
index 762405c6710bc..9e91c8dfe6e53 100644
--- a/tests/trainer/test_dataloaders.py
+++ b/tests/trainer/test_dataloaders.py
@@ -582,7 +582,7 @@ def test_dataloaders_with_fast_dev_run(tmpdir, fast_dev_run):
         assert trainer.max_epochs == 1
 
         trainer.fit(model)
-        assert not trainer.disable_validation
+        assert trainer.enable_validation
         assert trainer.num_training_batches == fast_dev_run
         assert trainer.num_val_batches == [fast_dev_run] * len(trainer.val_dataloaders)