Playboy, the company best known for barmaid bunnies and see-all centerfolds, is going back to a past life in South Florida.
The lifestyle brand just bought a Miami Beach hotel and plans to turn it into a “members only” private club, according to a financial disclosure with the U.S. Securities and Exchange Commission.
The move evokes a business model of decades past when Playboy owned a hotel on Collins Avenue and a club on Biscayne Boulevard.
Playboy, which also announced last year it is moving its headquarters from L.A. to South Beach, agreed to pay $12.5 million for the Freehand Hotel, best known for its Broken Shaker bar and its lush landscaping along Indian Creek.
The closing of the purchase of the cluster of five buildings at 27th Street and Indian Creek Driveis set for Dec. 15. The seller is London-based hotel brand Generator.
The company put up about $5 million for the deal and is looking to recoup that from the future sale of memberships to the private club, according to the SEC filing.
“We welcome the investment,” said Miami Beach City Commissioner Joseph Magazine. “South Florida continues to be an attractive place for capital investments in lifestyle and hospitality.”
The Freehand, built in 1936, won a Dade Heritage Trust Preservation Award in 2017 for its use and renovation of the historic buildings.
The buildings have 89 rooms and have doubled as both a hostel with shared rooms and an affordable hotel with private ones. The property features tropical fruit trees, and greens and herbs grown on a rooftop garden.
The Freehand is also known for the Broken Shaker, a popular and highly regarded bar that draws eclectic crowds. Playboy hasn’t yet specified plans for what it will keep or add at the hotel. The hotel website is accepting reservations into early December and the Broken Shaker remains open for business, according to both bar and hotel websites.
“Playboy will rehabilitate and revive it,” Commissioner Magazine, also chairman of the city’s finance committee, said of the property, and “will pay respect to the historic fabric of the building and the neighborhood.”
Playboy executives did not respond to a request from the Miami Herald for comment or more information about the company’s plans for the hotel.
Playboy’s past in South Florida
Playboy’s growing footprint in South Florida is a return of sorts.
South Florida’s original Playboy Club, with its bunny barmaids, opened in 1961 at 77th Street and Biscayne Boulevard in Miami. The site, across the street from an adult theater, is now an auto supply shop. The club moved to an inn near the airport in the early-‘80s, but shut down a few years later.
In 1970, Playboy poobah Hugh Hefner invested $15 million to open the Playboy Plaza in Miami Beach, creating a signature hotel from a former Hilton. A news article described it at the time: “The Playboy Plaza boasts 468 luxurious guest rooms plus an exciting selection of showroom lounges, restaurant and intimate bars staffed by beautiful bunnies.”
The hotel was later converted to condos and today is called the Castle Beach Club. But a time capsule remains in the vacant Playboy theater. Replete with a rich history even pre-dating Playboy, the theater is now up for sale.
Playboy’s headquarters move to South Beach
Forty years later, in 2025, Playboy announced it was returning to South Florida, with headquarters in the penthouse of a new luxury office building in Miami Beach called Rivani, 1691 Michigan Ave. near Lincoln Road. The company also announced plans for a future club.
Playboy called it a strategic move, and said then that it underscores the “brand’s next chapter with expanded hospitality offerings, advanced content studios and renewed cultural presence.” At the time, Playboy also said the company was developing a new Playboy Club in Miami Beach, including a “world-class restaurant” along with “an exclusive members-only space inspired by the storied Playboy Mansion.”
Playboy also is building content studios in the Rivani to support its “growing creator network,” Ben Kohn, CEO of Playboy Inc. told the Miami Herald in 2025. The studios will be home to the production of podcasts, photography and other media ventures.
“Our vision is to create world-class content and experiences that resonate globally,” Kohn said. He sees Miami Beach as “the ideal home for Playboy’s next chapter.”
Playboy has just about turned the page from its old chapter.
In 2020, the company ceased publishing its monthly Playboy magazine, founded in 1953 by Hefner and once the most identifiable part of the brand. In 2015, the magazine, also known for its in-depth articles along with the centerfolds, stripped nudity from its pages.
Playboy today has an 11-year lease for that office in the Rivani building. In the first year, it will pay about $2.1 million in rent.
Playboy has started hiring for its new Miami Beach headquarters. The city initially approved $200,000 in economic development initiatives for the first year of the contract, but so far hasn’t provided any money to the company, Commissioner Magazine said, because it hasn’t yet hit the required hiring threshold.
As of Sept. 30, Playboy hadn’t moved into the new headquarters, the SEC filing said.
