Puerto Rico boasts many historic hotels that maintain the original mystique and essence of the property while seamlessly incorporating modern amenities like fine dining restaurants and relaxing pools.

You can stroll the halls of the oldest convent in Puerto Rico, which was converted into a luxury hotel by a department store tycoon in the 1950s; wake up to an ocean view in what used to be the home of a Spanish artillery captain in the 1700s; or take a swim in the resort pool where jet setters of the 1950s and ‘60s spent their holiday vacations.

A stay at each of these hotels comes with its own unique story:

Room view at El Convento Hotel.

Ocean views from a room at the El Convento Hotel.

Hotel El Convento

100 Calle del Cristo, San Juan

In the heart of Old San Juan stands the imposing Hotel El Convento, a former Carmelite convent turned luxury hotel. Commissioned by a wealthy Spanish noblewoman in 1651, this was the first convent on Puerto Rico and was occupied by nuns until 1903.

After several decades empty, the building was acquired by Robert Frederic Woolworth, heir to the Woolworth fortune, who opened the European-style Hotel El Convento in 1962. From there, the hotel was taken over by the government, then passed to a group of local investors. After being closed for two years of renovations, Hotel El Convento reopened in 1997, restored to its original splendor.

Outside view of the Parador Guánica 1929.

The Parador Guánica 1929.

Parador Guánica 1929

Km 2.5 Los Veteranos Avenue, PR-3116, Guánica

As the name implies, Parador Guánica 1929 was constructed in the 1920s in the town of Ensenada, located in the municipality of Guánica on the south side of the island. The town isn’t much older than the hotel (1909) and was established by the South Porto Rico Sugar Company to house workers for the nearby sugar cane plantations and processing plant.

The hotel was originally named the American Hotel and featured architecture inspired by Spanish haciendas. Typical guests of the American Hotel were the executives, investors and politicians with stakes in what became the most powerful sugar company in the Caribbean. The current owners maintained the original 1920s architecture while making upgrades to the facilities and adding modern amenities.

Room view at the Condado Vanderbilt Hotel.

The elegance of the Condado Vanderbilt Hotel.

Condado Vanderbilt Hotel

1055 Ashford Ave, San Juan

The railroad tycoon Frederick William Vanderbilt commissioned the Condado Vanderbilt Hotel in 1917, when the now-affluent neighborhood of Condado was just a strip of palm tree-lined beach. The Warren & Wetmore architecture firm, famous for developing Grand Central Station in Manhattan and the New York Vanderbilt Hotel, designed the building in classic Spanish Revival style.

Opened in 1919, the hotel's stunning ocean views and opulent interiors attracted Hollywood and European royalty, including notable guests such as Errol Flynn, Bob Hope, Arthur Rubinstein, President Franklin Roosevelt and his wife Eleanor.

After several decades of name changes and renovations, the hotel closed its doors in the 1990s and was dormant until 2014. Under new management, it has been restored to the Old World sophistication and style that characterized much of its 100-year history.

Outside view of La Concha Hotel.

Outside view of La Concha Hotel.

La Concha A Renaissance Resort

1077 Ashford Ave, San Juan

During the 1950s, Puerto Rico came into its own as a tourism destination and, as a result, modern hotels started to appear — most notably Hotel La Concha a Renaissance Resort in Condado. Designed by architects Osvaldo Toro and Miguel Ferrer, the innovative style of the building is known as Tropical Modernism, which was inspired by nature to create distinctly modern spaces in a tropical context.

One of its most emblematic features is the double curved ceiling of the Perla banquet hall, originally named Club La Concha, which resembles the interior of a conch shell and features enormous glass windows overlooking the Atlantic Ocean. The hotel was inaugurated in 1958, and then reopened in 2007 after a $220 million renovation.

Room view at the Gallery Inn.

Room view at the Gallery Inn.

The Gallery Inn

Norzagaray 204, San Juan

In 1961, the artist Jan D'Esopo moved to Puerto Rico looking for inspiration and with the intention of setting up an art studio. On the north side of Old San Juan, on Norzagaray street, she fell in love with a building that was once the home of a Spanish artillery captain back in the 1730s. Parts of the building were in ruins, but the original bones were still intact.

Over the years, she transformed her home into 18 apartments and then The Gallery Inn, an artist alcove in the middle of the Old City where art, music and hospitality collide. Each room of the hotel features original artwork on its wall, sculptures are scattered throughout the property, and every window offers a view of either the ocean or the colorful buildings of Old San Juan.

View of the lobby at the Meliá Century Hotel in Ponce.

The lobby at the Meliá Century Hotel in Ponce.

Meliá Century Hotel

75 Calle Cristina, Ponce

On Plaza Las Delicias in the historic center of Ponce, the Meliá Century Hotel has stood the test of time, expanding and adapting with each passing decade. Built in 1895 by Don Bartolo Meliá, a Spanish merchant, the hotel began with nine rooms. In 1915, the Hotel Meliá expanded capacity to 21 rooms, which were designed in the neoclassical and modern styles by architect Alfredo Wiechers.

In 1940, the hotel added another 26 rooms developed by well-known local architect Francisco Porrata Doria, who added a balconied facade and pillars. A third expansion occurred in 1960, adding another 26 rooms. The hotel underwent its most recent renovation in 2014 when it came under new ownership. Meliá Century Hotel is the only hotel in Puerto Rico that has maintained uninterrupted operation for more than 120 years.

Chandelier at El San Juan Hotel

The elegant Chandelier Bar at the Fairmont El San Juan Hotel. 

Fairmont El San Juan Hotel

Nestled in two miles of the award-winning Isla Verde beach, Fairmont El San Juan Hotel is a gem of the 1960’s Puerto Rican hospitality. Designed by legendary architect Morris Lapidus in 1958, the resort became a beacon for tourists and iconic entertainers like Sammy Davis Jr., Nat King Cole, Frank Sinatra, Eddie Fisher, Carol Channing, and Liza Minelli, among other icons of the time. 

A grand chandelier remains as a testament of the era it was built, as the hotel followed a redesign to blend its timeless splendor with modern-tropical elegance.

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