The district occupies the southwestern part of the Karelian Isthmus. The landscape is hilly and forested, with many rock formations. The northern part of the district lies in the basin of the Vuoksi River, which drains into Lake Ladoga. The Vuoksi itself crosses the district from northwest to southeast. Other rivers in the district, the largest of which are the Gryaznovka and the Sestra, drain directly into the Gulf of Finland. There are many lakes in the district, especially in the basin of the Vuoksi. Lake Glubokoye is the largest one.
The western part of the Karelian Isthmus, inhabited by Karelians and Finns, historically lay between Russia and Sweden (later Russia and Finland) and changed hands on a regular basis. Vyborg was founded in 1293 as a Swedish fortress for protection from the Novgorod Republic. In 1323, the Treaty of Nöteborg established the border between Novgorod and Sweden along the Sestra River. This border corresponds to the current southern limits of Vyborgsky District. In 1403, Vyborg was chartered. The Novgorod Republic besieged Vyborg in 1411, and the Grand Duchy of Moscow, which by then annexed Novgorod, besieged it in 1495, but on both occasions the fortress was not conquered. According to the Treaty of Stolbovo, the whole Karelian Isthmus was ceded to Sweden and the border moved southeast. In 1710, during the Great Northern War, the troops of Tsar Peter the Great conquered Vyborg, and eventually the whole area was annexed to Russia. This was confirmed by the Treaty of Nystad in 1721.
In the course of the administrative reform carried out in 1708 by Peter the Great, the area was included into Ingermanland Governorate (known since 1710 as Saint Petersburg Governorate). In 1719, it became a part of Vyborg Province, and in 1744, Vyborg Governorate with the seat in Vyborg was established. In 1783, it was transformed into Vyborg Viceroyalty, then in 1801 back into Vyborg Governorate. In 1801, Vyborg Governorate was renamed Finland Governorate, and in 1812, it was renamed back and included into the Grand Duchy of Finland, which had previously been ceded to Russia by Sweden. After 1812, it was known as the Viipuri Province. On July 17, 1919, the Viipuri Province became a part of independent Finland. The border between Finland and Soviet Union was drawn along the Sestra River.
After the Winter War, Finland ceded this territory to the Soviet Union by the terms of the Moscow Peace Treaty. The territory was recaptured by Finns between 1941 and 1944 during the Continuation War but was again ceded to the Soviets after the Moscow Armistice. The secession was formalized after signing of the Paris Peace Treaty in 1947. Viipuri Province was divided, with the larger part ceded to Soviet Union and the smaller part remaining in Finland. The population was resettled to Finland and replaced by migrants from Central Russia.
Vyborgsky District with the administrative center in Vyborg was established in March 1940 as a part of the Karelian Autonomous Soviet Socialist Republic (Karelian ASSR). On March 31, 1940, the Karelian ASSR was transformed into the Karelo-Finnish Soviet Socialist Republic. On November 24, 1944, Vyborgsky District was transferred from Karelo-Finnish Soviet Socialist Republic to Leningrad Oblast.
Another district established in March 1940 was Yaskinsky District with the administrative center in the work settlement of Yaski (Jääski). It was a part of the Karelian ASSR, and of the Karelo-Finnish Soviet Socialist Republic after March 31, 1940. On November 24, 1944, Yaskinsky District was transferred from Karelo-Finnish Soviet Socialist Republic to Leningrad Oblast. On October 1, 1948, the district was renamed Lesogorsky, and on January 13, 1949, all localities whose names originated in Finnish were renamed using Russian names. In particular, Yaski was renamed Lesogorsky and Enso was renamed Svetogorsk. On December 9, 1960, Lesogorsky District was abolished and merged into Vyborgsky District.
On May 16, 1940, Kannelyarvsky District with the administrative center in the selo of Kennelyarvi (Kanneljärvi) was established as well. It was a part of Leningrad Oblast. On August 22, 1945, the administrative center of the district was moved from Kennelyarvi to the selo of Rayvola (Raivola) and the district was renamed Rayvolovsky. On October 1, 1948, the district was renamed Roshchinsky, and on January 12, 1949, all localities whose names originated in Finnish were renamed using Russian names. In particular, Rayvola was renamed Roshchino. On July 31, 1959, Roshchino was granted urban-type settlement status. On February 1, 1963, Roshchinsky District was abolished and merged into Vyborgsky District.