In early 1946, as part of the Puerto Rican industrialization effort known as Operation Bootstrap, the Puerto Rico Industrial Development Co. decided to erect a modern luxury hotel. The facility would be owned by the Commonwealth of Puerto Rico, but leased to the multinational hospitality operator that provided the better bid. The hotel would have 300 bedrooms, the necessary ancillary facilities, and be located adjacent to Fortín de San Gerónimo in Puerta de Tierra. A competition was held to select the design, with three architectural firms in Puerto Rico invited: Schimmelpfennig, Ruiz y González; The Office of Henry Klumb; and Toro Ferrer. Two additional firms from Florida were also invited to participate: Frederick G. Seelman from Palm Beach and Robert Swartburg from Miami. These two firms submitted Spanish Renaissance-style designs, while the three Puerto Rican firms presented modern designs inspired by the International style. The final design chosen was by Toro Ferrer, who also designed the Modern Movement-style Supreme Court Building in San Juan. To operate the hotel, the Puerto Rico Industrial Development Co. invited seven leading American hotel firms. Conrad Hilton, being from New Mexico, opened his letter back with "Mi estimado amigo" and won over the Puerto Ricans. The hotel opened on December 9, 1949. It was Hilton's first hotel outside the continental United States and made Hilton the first international hotel company. The government-backed Puerto Rico Industrial Development Corp. spent $7 million to build and furnish the hotel. After it was built, the government leased the hotel to the Hilton Corp. on a 20-year lease. The hotel was the first in Puerto Rico to offer radios in every room and individually controlled air conditioners. Guests for the opening included Gloria Swanson, Eastern Air Lines President Eddie Rickenbacker, David Rockefeller and numerous other celebrities and notables. The hotel claims to be the birthplace of the Piña colada. In 1954, bartender Ramón “Monchito” Marrero spent three months creating a mix of rum, coconut cream, and pineapple juice. The drink was first served on August 15, 1954. The original hotel was expanded over the years from 300 rooms to 646 rooms. After managing the hotel for 48 years, Hilton International bought the property in 1998. Hilton closed the hotel the following year for a complete renovation, lasting nine months. It reopened on December 25, 1999 celebrating its 50th anniversary after $50 million in renovations. In 2005, the hotel was expanded with the huge Paseo Caribe complex, including shops, restaurants, and 264 villas marketed as the Condado Lagoon Villas. In January 2017, ownership of the hotel was transferred to Park Hotels & Resorts when that company was spun off from Hilton Worldwide. In September 2017, the hotel was heavily damaged by Hurricane Maria, forcing it to close. It reopened in May 2019, following a US$100 million renovation.
Famous guests
Its first of many famous guests were Gloria Swanson and Gertrude Ederle. Between the 1960s and 1980s, many important performers either worked or stayed at the Caribe Hilton, including Marco Antonio Muñiz. Other famous guests have included many world champion boxers during Puerto Rico's golden era of boxing. The nationalbasketball teams of twelve countries also stayed there for 2003's pre-Olympic tournament of the Americas.
Some scenes from were filmed in various areas of the hotel, which was called the Caribe Paradise Resort. It is also the setting for Hunter S. Thompson's The Rum Diary. "22 Jump Street" was also filmed in the lobby of the hotel.