The settlement remained rudimentary for many years. A school began operating in 1884 and moved into purpose-built premises three years later. The first store wasn't opened until Welshman Jackie Jones began selling goods from an upturned boat in the late 1880s. Rosebud suffered from a lack of direct access to Melbourne. When a pier was finally built in 1888, it failed to extend into the deep water, so ferries and passenger ships from the metropolis had to dock at Dromana, a larger town about eight km to the north. A road was formed by clearing a path at Anthonys Nose, the point where Arthurs Seat (305m) meets the sea, halfway between Rosebud and Dromana. This, at last, gave Rosebud a road connection to surrounding towns and Melbourne. The Post Office then opened on 27 March 1889. 
Although some companies offered ferry passengers a ride to Rosebud after they disembarked at Dromana, the bulk of the tourism trade went to Dromana and nearby Arthurs Seat, while Dromana remained the transportation hub for goods brought by road and sea.
In the early twentieth century, developers attempted to market Rosebud as an English-style seaside resort with the creation of the Clacton-on-sea estate (today known as the "avenues"). Vacant land was offered at just 2 pounds per block in an effort to stimulate investment in the area. Take up was slow; society wasn't affluent enough to allow many of the middle class to own holiday homes so far from the city. This slow growth continued in the inter-war years; the township consisted of about ten shops and a presbyterian church, built of wood on a single day in 1923. The first pub (the Rosebud Hotel) wasn't built until 1939-40. Built in the prevailing art deco style, it remains the only pub in the town to this day.
Local businessmen had noticed a slowly growing phenomenon in the late 1930s and 1940s - the popularity of camping on the Rosebud foreshore, a cheap and interesting alternative to staying at guesthouses or hotels. After World War II, aided by the explosion in the number of people owning a car, camping at Rosebud over the Christmas-New Year holidays became a tradition for many Melbourne families. The Rosebud Foreshore Committee was set up to administer the area and take bookings, which are now made twelve months in advance. By the twenty first century, camping on the foreshore has taken on a cultural dimension and there are families who are fourth and even fifth generation visitors. Many Melburnians can reminisce about summer holidays at Rosebud.
By the 1960s, Rosebud had emerged as the largest town on the southern peninsula, complete with a shopping centre and extensive sporting facilities. In time it became home to an increasing number of permanent residents. The town's shopping strip and most of its amenities are located on an extended strip of the Nepean Highway, which runs parallel to the beach. Rosebud proper extends from Lonsdale Street (the border with McCrae) for 3km to Boneo Road, where Rosebud West begins, while Rosebud South is a pocket of suburban streets directly south of Rosebud on the foothills of Arthurs Seat.
Rosebud is shielded by camping grounds lined with banksias, tea tree and sheoak. During the summer months and as late as Easter campers can be found in these areas. Rosebud is one of the main towns on the Mornington Peninsula mostly because of its shopping areas. Rosebud Plaza (formerly known as Port Phillip Plaza) has undergone major redevelopment and now includes K-Mart, Safeway, Coles and Target. The second shopping centre in the town is the Rosebud Centro which includes Safeway and nearby is IGA and Rosebud Cinemas. There is also a shopping strip along the Nepean Highway.