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Just a short crosswalk away from the world's most famous beach is one of Waikiki's most popular hotels, the Sheraton Princess Kaiulani. The 1,142-room hotel sits on the former Ainahau Estate, where the last princess of Hawaii called home. The ten-acre oasis was complete with lush gardens, ponds, and the Victorian-style home owned by Princess Victoria Kaiulani and her father, Archibald Cleghorn, the Governor of Oahu. Since 1955, the hotel has captured the warmth of a true Hawaiian home, calling back visitors year after year.

Waikiki didn't always have the Sheraton Princess Kaiulani. After the war years, tourism in the mid-1950's reached a new peak in Hawaii. Regularly scheduled airline services from the West Coast boosted Honolulu as an accessible, desirable travel destination. With Transatlantic Ocean's new packaged group tours, cost-wary travelers who used to spend days on an ocean liner could now affordably board a plane and reach Hawaii in a few hours. Trade was also rapidly on the rise. To capitalize on this increasing boom in travel and trade, Matson constructed its third hotel, the Princess Kaiulani in 1955.

Formerly the site of the Moana cottages, the land was cleared in 1953 to make way for a new high-rise. The architectural firm Gardner A. Dailey, F.A.I.A and Associates designed the new hotel and Pacific Construction Company built it at an approximate cost of $4.5 million. The site for the hotel was on the old Waikiki Road, now the bustling Kalakaua Avenue.

The entrance to the hotel's parking lot marks the approximate arched entrance to Governor Cleghorn's Ainahau garden, filled with flora from the islands and around the world. Princess Kaiulani would enter the estate from Waikiki through her private driveway located just near the arched entrance. She winded through rows of palm trees to reach the white, Victorian-style house set deep within the grounds. Because it stood on the former entrance of the royal Ainahau Estate, the hotel was named in honor of Hawaii's most beloved monarch, Princess Kaiulani.

The hotel opened on June 11, 1955, which was also Kamehameha Day, celebrating the birthday of the first King of all Hawaii. At the time, the hotel's Princess Wing was the tallest building in Hawaii (11 stories, 131 feet above the ground). It was the largest hotel built in Hawaii since The Royal Hawaiian in 1927. More than 100 guests, including Matson officials, community leaders, and government officials were on hand to celebrate the opening of the
Princess Kaiulani Hotel. A near-life size portrait of Princess Kaiulani painted by Hawaii artist, Lloyd Sexton, was dedicated in the main lobby following a lei ceremony. 

The Princess Kaiulani Hotel touted their “every room with a view.” Each makai (ocean) room had a spacious balcony furnished with lounging chairs, allowing a view of Waikiki Beach and the shore from Diamond Head to Pearl Harbor. Mauka (mountain) rooms had broad picture windows. The original hotel lobby design and motif was Polynesian with terrazzo floors, columns paneled in golden Philippine mahogany and furniture framed in Koa wood and upholstered in bright fabric. A tropics and Orient setting surrounded the Orchid Pool. A Japanese fence enclosed the grounds on three sides and contained thousands of Japanese willow branches closely woven together.

The top floor of the hotel was dedicated to public rooms, including the Robert Louis Stevenson Room, named for the famed poet and author who befriended the princess. The architects designed the entire 11th floor to open into panoramic views of Waikiki Beach. Twelve luxury penthouse suites were added in 1959.

In 1959, the year Hawaii entered statehood; Matson sold all of its hotel properties, including the four year-old Princess Kaiulani Hotel, to the Sheraton hotel chain. The Diamond Head Wing (now the Kaiulani Wing) opened in September 1960 at a cost of $2.8 million, adding 210 rooms. A showroom seating up to 700 was added to the property, as well as a 275-car garage. In 1963, Sheraton sold all of its Hawaiian hotels to Kyo-ya Company, Ltd., while continuing to manage the hotels under the Sheraton name with a long-term contract. The last wing of the Sheraton Princess Kaiulani, the 29-floor Ainahau Tower, opened in 1970.

For more information on the Sheraton Princess Kaiulani, please call the hotel at 1-808-922-5811 in the United States and Canada.