diff --git a/app/Eloquent/Models/Vacation.php b/app/Eloquent/Models/Vacation.php
index 232fcfe..c22cf76 100644
--- a/app/Eloquent/Models/Vacation.php
+++ b/app/Eloquent/Models/Vacation.php
@@ -12,7 +12,6 @@ use Illuminate\Support\Carbon;
 /**
  * @property int $id
  * @property Carbon $date
- * @property string $event_id
  * @property User $user
  * @property VacationRequest $vacationRequest
  * @property YearPeriod $yearPeriod
diff --git a/app/Eloquent/Models/VacationRequest.php b/app/Eloquent/Models/VacationRequest.php
index 0b36764..0f7348a 100644
--- a/app/Eloquent/Models/VacationRequest.php
+++ b/app/Eloquent/Models/VacationRequest.php
@@ -6,6 +6,7 @@ namespace Toby\Eloquent\Models;
 
 use Database\Factories\VacationRequestFactory;
 use Illuminate\Database\Eloquent\Builder;
+use Illuminate\Database\Eloquent\Casts\AsCollection;
 use Illuminate\Database\Eloquent\Factories\HasFactory;
 use Illuminate\Database\Eloquent\Model;
 use Illuminate\Database\Eloquent\Relations\BelongsTo;
@@ -29,6 +30,7 @@ use Toby\Domain\States\VacationRequest\VacationRequestState;
  * @property YearPeriod $yearPeriod
  * @property Collection $activities
  * @property Collection $vacations
+ * @property Collection $event_ids
  * @property Carbon $created_at
  * @property Carbon $updated_at
  */
@@ -44,6 +46,7 @@ class VacationRequest extends Model
         "state" => VacationRequestState::class,
         "from" => "date",
         "to" => "date",
+        "event_ids" => AsCollection::class,
     ];
 
     public function user(): BelongsTo
diff --git a/app/Infrastructure/Jobs/ClearVacationRequestDaysInGoogleCalendar.php b/app/Infrastructure/Jobs/ClearVacationRequestDaysInGoogleCalendar.php
index 4ae157d..ec5e6ff 100644
--- a/app/Infrastructure/Jobs/ClearVacationRequestDaysInGoogleCalendar.php
+++ b/app/Infrastructure/Jobs/ClearVacationRequestDaysInGoogleCalendar.php
@@ -8,7 +8,6 @@ use Illuminate\Bus\Queueable;
 use Illuminate\Contracts\Queue\ShouldQueue;
 use Illuminate\Foundation\Bus\Dispatchable;
 use Spatie\GoogleCalendar\Event;
-use Toby\Eloquent\Models\Vacation;
 use Toby\Eloquent\Models\VacationRequest;
 
 class ClearVacationRequestDaysInGoogleCalendar implements ShouldQueue
@@ -22,17 +21,16 @@ class ClearVacationRequestDaysInGoogleCalendar implements ShouldQueue
 
     public function handle(): void
     {
-        $vacations = $this->vacationRequest->vacations()
-            ->whereNotNull("event_id")
-            ->get();
+        foreach ($this->vacationRequest->event_ids as $eventId) {
+            $calendarEvent = Event::find($eventId);
 
-        /** @var Vacation $vacation */
-        foreach ($vacations as $vacation) {
-            Event::find($vacation->event_id)->delete();
-
-            $vacation->update([
-                "event_id" => null,
-            ]);
+            if ($calendarEvent->googleEvent->getStatus() !== "cancelled") {
+                $calendarEvent->delete();
+            }
         }
+
+        $this->vacationRequest->update([
+            "event_ids" => null,
+        ]);
     }
 }
diff --git a/app/Infrastructure/Jobs/SendVacationRequestDaysToGoogleCalendar.php b/app/Infrastructure/Jobs/SendVacationRequestDaysToGoogleCalendar.php
index d00201a..04082b1 100644
--- a/app/Infrastructure/Jobs/SendVacationRequestDaysToGoogleCalendar.php
+++ b/app/Infrastructure/Jobs/SendVacationRequestDaysToGoogleCalendar.php
@@ -7,8 +7,9 @@ namespace Toby\Infrastructure\Jobs;
 use Illuminate\Bus\Queueable;
 use Illuminate\Contracts\Queue\ShouldQueue;
 use Illuminate\Foundation\Bus\Dispatchable;
+use Illuminate\Support\Carbon;
+use Illuminate\Support\Collection;
 use Spatie\GoogleCalendar\Event;
-use Toby\Eloquent\Models\Vacation;
 use Toby\Eloquent\Models\VacationRequest;
 
 class SendVacationRequestDaysToGoogleCalendar implements ShouldQueue
@@ -22,21 +23,55 @@ class SendVacationRequestDaysToGoogleCalendar implements ShouldQueue
 
     public function handle(): void
     {
-        $vacations = $this->vacationRequest->vacations()
-            ->whereNull("event_id")
-            ->get();
+        $days = $this->vacationRequest
+            ->vacations()
+            ->orderBy("date")
+            ->pluck("date");
 
-        /** @var Vacation $vacation */
-        foreach ($vacations as $vacation) {
+        $this->vacationRequest->event_ids = new Collection();
+        $ranges = $this->prepareRanges($days);
+
+        foreach ($ranges as $range) {
             $event = Event::create([
                 "name" => "{$this->vacationRequest->type->label()} - {$this->vacationRequest->user->fullName}",
-                "startDate" => $vacation->date,
-                "endDate" => $vacation->date,
+                "startDate" => Carbon::create($range["from"]),
+                "endDate" => Carbon::create($range["to"])->addDay(),
             ]);
 
-            $vacation->update([
-                "event_id" => $event->id,
-            ]);
+            $this->vacationRequest->event_ids->add($event->id);
         }
+
+        $this->vacationRequest->save();
+    }
+
+    protected function prepareRanges(Collection $days): array
+    {
+        $ranges = [];
+        $index = 0;
+        $first = $days->shift();
+
+        $ranges[$index] = [
+            "from" => $first,
+            "to" => $first,
+        ];
+
+        foreach ($days as $day) {
+            if ($day->diffInDays($ranges[$index]["to"]) !== 1) {
+                $index++;
+
+                $ranges[$index] = [
+                    "from" => $day,
+                    "to" => $day,
+                ];
+
+                continue;
+            }
+
+            if ($day->isAfter($ranges[$index]["to"])) {
+                $ranges[$index]["to"] = $day;
+            }
+        }
+
+        return $ranges;
     }
 }
diff --git a/database/migrations/2022_03_17_105827_remove_event_id_from_vacations_table.php b/database/migrations/2022_03_17_105827_remove_event_id_from_vacations_table.php
new file mode 100644
index 0000000..b5f8c8a
--- /dev/null
+++ b/database/migrations/2022_03_17_105827_remove_event_id_from_vacations_table.php
@@ -0,0 +1,23 @@
+<?php
+
+declare(strict_types=1);
+
+use Illuminate\Database\Migrations\Migration;
+use Illuminate\Database\Schema\Blueprint;
+use Illuminate\Support\Facades\Schema;
+
+return new class() extends Migration {
+    public function up(): void
+    {
+        Schema::table("vacations", function (Blueprint $table): void {
+            $table->dropColumn("event_id");
+        });
+    }
+
+    public function down(): void
+    {
+        Schema::table("vacations", function (Blueprint $table): void {
+            $table->string("event_id")->nullable();
+        });
+    }
+};
diff --git a/database/migrations/2022_03_17_105927_add_event_ids_column_to_vacation_requests_table.php b/database/migrations/2022_03_17_105927_add_event_ids_column_to_vacation_requests_table.php
new file mode 100644
index 0000000..571f1ee
--- /dev/null
+++ b/database/migrations/2022_03_17_105927_add_event_ids_column_to_vacation_requests_table.php
@@ -0,0 +1,23 @@
+<?php
+
+declare(strict_types=1);
+
+use Illuminate\Database\Migrations\Migration;
+use Illuminate\Database\Schema\Blueprint;
+use Illuminate\Support\Facades\Schema;
+
+return new class() extends Migration {
+    public function up(): void
+    {
+        Schema::table("vacation_requests", function (Blueprint $table): void {
+            $table->json("event_ids")->nullable();
+        });
+    }
+
+    public function down(): void
+    {
+        Schema::table("vacation_requests", function (Blueprint $table): void {
+            $table->dropColumn("event_ids");
+        });
+    }
+};