Heat olive oil in a large skillet over medium-high heat.
Add ground beef to the skillet and cook, breaking it apart with a spoon, until browned and cooked through, about 5-7 minutes.
Add diced onion and minced garlic to the skillet with the beef and cook until the onion is softened, about 3 minutes.
Add diced bell peppers to the skillet and cook for an additional 3 minutes, stirring occasionally.
Stir in the rinsed rice, diced tomatoes with their juice, beef broth, dried Italian seasoning, salt, and black pepper.
Bring the mixture to a boil, then reduce heat to low, cover the skillet, and simmer for 18-20 minutes or until the rice is tender and liquid is absorbed.
Remove the skillet from heat and sprinkle shredded cheddar cheese evenly over the top.
Cover the skillet again and let it sit for 2-3 minutes until the cheese melts.
Fluff the mixture with a fork and serve warm.