Oleshky (Ukrainian: Олешки, pronounced [oˈlɛʃkɪ] ^ⓘ), previously known as Tsiurupynsk from 1928 to 2016, is a city in Kherson Raion, Kherson Oblast, southern Ukraine, located on the left bank of the Dnieper River with the town of Solontsi to the south. It is the oldest city of the oblast and one of the oldest in southern Ukraine. It is known for its proximity to the Oleshky Sands, a large desert region. Oleshky is the site of artist Polina Rayko's home, a national cultural monument of Ukraine. It also hosts the administration of Oleshky urban hromada, one of the hromadas of Ukraine. It had a population of 24,124 (2022 estimate). As of 2025, the city is occupied by Russia.

The city is located in the south of Ukraine, near Kherson. It is a port on the Konka River. The Oleshky Sands are located in close proximity to the town.

The area around Oleshky has been known since antiquity. Herodotus mentioned Scythian forests in the mouth of the Dnieper in the 5th century BCE, which were called "Oleshye" (from the Slavic word for forest) by the Slavs. The area has been inhabited since ancient times: stone molds for metal casting have been found near the city dating back to the Late Bronze Age, indicating the existence of a bronze tool workshop.

The settlement of Oleshia has been known since medieval times. Its name was derived from the forest area, and is related to the modern name "Oleshky". Until the 10th century, the town belonged to the Byzantine sphere of influence, but then became a client of Kievan Rus.

It is believed by some historians that Oleshia existed from the 10th to the 13th century as a large Slavic trading city, which was a stronghold of Kievan Rus in the lower Dnieper. It was a major port and important fishing site. A trade route from Kyiv to Byzantium and the Transnistria region ran through the city. Eventually, the site of Oleshia became a Genoese trade colony. In the mid-15th century, Oleshia was destroyed by the Ottoman Empire, who established Ochakiv nearby as a post to control the Dnieper River.

From the 15th to 18th century, the territory of modern Oleshky was under the control of the Crimean Khanate, who permitted the Zaporozhian Cossacks to settle there. After the Cossacks sided with the enemies of Russian Tsar Peter the Great, they were driven from their settlements along the Kamianka River in 1711. The Crimean Khanate permitted the Zaporozhians to establish a Sich on the Khanate's territory. The Cossacks established the Oleshky Sich [uk] above the Dnieper–Bug estuary near where the modern town of Oleshky is located. Eventually in 1734, the Cossacks were officially allowed to return to the Russian Empire.

Intensive settlement of the region around Oleshky began in 1783 after the annexation of Crimea by the Russian Empire. In May 1784, fifty state peasants settled at the site of the Cossack fortress Oleshky and founded a settlement of the same name. In 1785, they were joined by another 258 people. The settlement was originally part of Taurida Oblast, until this administrative unit was abolished in 1796. It was transferred to the short-lived second Novorossiya Governorate until that too was abolished in 1802. In 1802, after the formation of the Taurida Governorate, Oleshky became the seat of Dneprovsky Uyezd within the governorate. Oleshky was also granted town status.

The Tsarist government was interested in rapidly settling the Taurida region. Due to this as well as Oleshky's status as uyezd center, contributed to rapid growth of the small town during the early 19th century. In addition to state peasants, other citizens from various backgrounds settled in the town. By 1832-33, 2,908 people lived in the town, and there were 430 houses. The population grew rapidly again during the Crimean War in 1853–1856, when Oleshky became a supply point for the Russian army, and troops passed through the town on their way to defend Sevastopol. By 1859, the number of residents in Oleshki had reached 6,500 people.