For more than a hundred years a hotel stood on this site, the very first building overlooking the southern end of Bondi Beach. The original building was named the Cliff House Hotel and was built around 1880. The Cliff House was demolished in the early 1920s and a new hotel built by Mr. Jack Shaw around 1926. It was called the Hotel International. Mr. Shaw did not own the hotel for long however; shortly after the Catholic Church turned down his offer for the use of the hotel for a convention, business went downhill. Shaw became disenchanted and sold the Hotel International to the hotelier, newspaper owner and sporting personality, Sir Joynton Smith, who named it the Astra.

In 1937, Oldfield’s Hotels Pty Ltd, owned by Mr. Allen Oldfield and his three sons, took control of the hotel. They had previously owned hotels in Captain’s Flat and Goulburn, and it was under the Oldfields' leadership that the Astra flourished. The first floor, namely The Casino Bar, was a dining room with linen table cloths and excellent cuisine. The room accommodated 100 diners and there was always an orchestra entertaining the patrons. It was noted for its Christmas dinners, with bookings being taken two months ahead! People would come and sit in the big leather chairs, listen to the music in the lounge and engage in conversation. Waiters, including Peter Finch it is said, would serve drinks. There was a dress code for the top floor, and if you did not dress properly you were not permitted to enter. Furthermore, if you were not there by 3pm there was nowhere to sit!

During World War II it was taken over by the government for the air force and later by the British wrens.

The Astra was on a par with the Hotel Australia, the old Wentworth and the Usher's Hotel; the Bondi Hotel was not in the same class. Parts of the movie Summer of the Seventeenth Doll with Ernest Borgnine, John Mills, Angela Lansbury and Anne Baxter were filmed at the Astra in 1959. The long island bar with eight taps was then one of the largest in Sydney. It was all tiles, cream and green, but classy and well kept. There was a lot of spit and polish, and one end of the snack bar was famous for its pies. People came from miles around and ordered them by the dozen.

Oldfield's sold the Astra in December 1967 for about $700,000 to Intercapital Hotels Pty Ltd; “We’d been there for 30 years and that was sufficient,” they said. In 1973, Intercapital changed its name to Castle Hotels Pty Ltd and its holding company was taken over by Cambridge Credit Corporation Ltd, who then sold the hotel to CG Maloney.

After a few years, Bondi residents took a petition to Waverley Council complaining that the Astra patrons were habitually disturbing the neighbourhood. The council in turn took it to the Metropolitan Licensing Board, and after lengthy hearings the Astra submitted a development application to become a retirement village. On 22nd October 1984 Bondi Beach Astra Retirement Village was opened by Mr. John Brown, Minister for Sport, Recreation and Tourism. These days, the building hosts a thriving community of over 55-year olds who love to take advantage of its fabulous Bondi location and rich heritage.