Toledo is a very touristic city and has many places to enjoy nightlife.
Around the Plaza de Cuba, in the new city, near the Roman circus, there are a multitude of places where you can have "tapas", beer, wine and other drinks. A few suggestions: La Darra, El Pasito (good wines), El Zahorí (during the daytime it is a bar and turns into a pub in the evening), Cervecería Santa Brava (a classic), La Vaca del Cielo (drink and dancing), El Horreo (restaurant).
In the old city, near the Plaza de Zocodover, there are some interesting places like El Trebol (c/ Santa Fe) and La Abadía (c/ Alfileritos), famous for their "pulgas" (literally "fleas"), delicious small sandwiches in baguette bread. There is a great variety of them. La Abadía is also famous for its caves. Nearby is El Pícaro, a good place for drinks.
Outside the city, and near el Cigarral de las Mercedes, Terraza Monterrey combines a quiet area for drinks and talk with a more lively area for dancing. It is usually very crowded.
Near the Puente de San Martín, not far from Terraza Monterrey is the Venta del Alma. It is and old inn from the 15th century. It has an indoor area for dancing and also a courtyard with a quieter atmosphere. Crowded.
There are some other terrazas opposite the "Estación de autobuses". Less crowded than the other places.
The Parador, outside the city (only by car or taxi) is a quiet place to have a coffee. If you want to enjoy the best view of the city don't miss it. It is superb, especially at night.
For late nighters, Sythons is an after hours disco in a very small street near the Alcázar. Everybody knows it. It is the closest place to the "Residencia". It is usually quite crowded, hot and smoky, but you can dance and drink until even later than sunrise. Don't miss the following day's Workshop events.