James Deering first beheld Vizcaya's completed main house on Christmas Day, 1916. According to accounts of the occasion, his designer—Paul Chalfin—staged an elaborate theatrical ceremony for Deering's arrival by Venetian gondola: miniature antique canons fired a salute, and friends dressed in Chalfin-designed Italian peasant costumes danced to Italian folk music. Chinese lanterns hung from the trees in the gardens, the construction of which would continue until 1922.

When he was in residence at Vizcaya during the winter months, Deering hosted parties for visiting luminaries such as film stars Lillian Gish and Marion Davies, politician William Jennings Bryan, inventor Thomas Edison, artist John Singer Sargent, and President Warren G. Harding, as well as family and less famous friends. Deering also entertained his guests on the two yachts that he maintained at Vizcaya: Psyche and Nepenthe. To help Deering maintain the illusion of carefree luxury, housekeeper Cecelia Adair and twelve of her staff members were readily available, and lived in rooms on the mezzanine and third floor of Vizcaya's two western towers. Running Vizcaya to Deering's standards was a monumental task. Laundry was done by hand and dried discreetly in walled yards; carpets, curtains and linens were removed, cleaned, and stored at the end of the season; and each summer, every book in the library was wrapped in newspaper to discourage insect infestation. Deering also owned pet monkeys and birds, which required care in his absence.

The village, located across what is now South Miami Avenue, was built between 1917 and 1922 to house staff—such as a chauffeur, a French chef, a pastry chef, and the estate superintendent—and to support life in the main house. A greenhouse supplied fresh flowers, fruit, and vegetables for Deering, his guests, and staff. Cows provided milk, and chickens furnished a ready supply of fresh eggs. A farm stand sold surplus eggs and produce, although the income generated was surely negligible. On the precious bayfront property, Deering and Chalfin set aside an area for staff members to use as their own private beach. A simple dance platform encouraged recreation after a day's hard work.