The area was inhabited for approximately 8,000 years by Native Americans of the Fernandeño-Tataviam and Chumash-Venturaño tribes that lived in the Santa Monica Mountains and Simi Hills and close to the Arroyo Calabasas (Calabasas Creek) tributary of the Los Angeles River in present-day Woodland Hills. The first Europeans to enter the San Fernando Valley were the Portola Expedition in 1769, exploring 'Alta California' for Spanish missions and settlements locations. Seeing it from present-day Sepulveda Pass, the oak savanna inspired them to call the area Santa Catalina de Bononia de Los Encinos (Valley of the Oaks). The Mission San Fernando Rey de España (Mission San Fernando) was established in 1797 and given the Valley's land, including future Woodland Hills. After the Mexican War of Independence the secularized Mission lands became the Rancho Ex-Mission San Fernando.

Woodland Hills is often very hot during the summer and gets very cool in the winter; on some winter nights the temperature has been known to dip below freezing. In July 2006 Woodland Hills recorded the highest temperature ever in Los Angeles County, hitting 119 °F at Los Angeles Pierce College. The climate is classified as a Csa in the Köppen climate classification, which is characterised by mild rainy winters and hot dry summers. This climate is often referred to as a Mediterranean climate. The precipitation of Woodland Hills ranges from 17 to 23 inches annually: the lower amount of annual rainfall is in the lower portions in the Valley, whereas the higher amounts are in the hills surrounding. Nonnatural flora often grown in the area is typical of Mediterranean vegetation: citrus, lavender, rosemary, cypress and many others.

It is also home to The Woodland Hills Recreation Center (Shoup Park) a 19-acre park. The park has a small indoor gymnasium without weights and with a capacity of 300; it may be used as an auditorium. The park also has a lighted baseball diamond, outdoor lighted basketball courts, a children's play area, a lighted American football field, picnic tables, a lighted soccer (football) field, and lighted tennis courts. Woodland Hills Pool is an outdoor seasonal unheated swimming pool.

The Warner Center Park, also known as Warner Ranch Park, is also located in Woodland Hills. The park, unstaffed and unlocked, has a children's play area and picnic tables. Serrania Park in Woodland Hills is an unstaffed, unlocked pocket park. It has a children's play area, hiking trails, and picnic tables. Alizondo Drive Park in Woodland Hills is an unstaffed, unlocked, and undeveloped park used for brush clearance once per year.

Along the western boundary of Woodland Hills is the large Upper Las Virgenes Canyon Open Space Preserve, a regional park with a trail network for miles of hiking, mountain biking, and equestrian rides. The trailhead and parking are at the very western end of Victory Boulevard in Woodland Hills. Scheduled walks and programs are offered. The Santa Monica Mountains National Recreation Area has various parks nearby to the south of the community. The Top of Topanga Overlook gives panoramic views of the verdant Woodland Hills neighborhoods and the Valley.