Calle 21 y O, Vedado, Plaza, La Habana 10400, Cuba
No pool on this list has had a more eventful life than the one at the Hotel Nacional de Cuba. Opened in December 1930, the hotel was designed by McKim, Mead & White — the same New York firm behind Penn Station and the original Madison Square Garden — and was built on a hilltop overlooking the Straits of Florida, allegedly financed in part with mob money. Within three years of opening, 400 army officers loyal to the deposed Cuban president barricaded themselves inside and were bombarded from land and sea by government troops. The hotel survived, bearing the pockmarked signs of the siege, and promptly got back to the business of being glamorous.
" A 1930s Art Deco landmark perched on a rocky outcrop overlooking the Malecón, declared a National Monument and honoured with UNESCO Memory of the World status.
The pool attracted a guest list so absurd it reads like someone shuffled a deck of cards containing every famous person of the twentieth century: Gary Cooper, Errol Flynn, Fred Astaire, Rita Hayworth, Marlene Dietrich, Marlon Brando, Winston Churchill, Walt Disney, Nat King Cole, and Johnny Weissmuller, who reportedly impressed the staff by jumping from a second-floor window directly into the pool — which, for a man who played Tarzan for a living, was probably the minimum expected. The hallways are lined with photographs of every famous guest who ever stayed, over 300 faces in the hotel's Hall of Fame, with rooms named after the biggest names, including the Ava Gardner room and the Frank Sinatra room.
In December 1946, the hotel hosted the Havana Conference, an infamous mob summit organised by Lucky Luciano and Meyer Lansky to carve up the casino business. Frank Sinatra was the entertainment, though officially he was just there on holiday; the entire hotel had been booked by the dons for their families to spend Christmas in the city. Five years later, Sinatra returned on honeymoon with Ava Gardner. They took a third-floor suite and, the story goes, he kept her there for most of the trip — which is either deeply romantic or deeply Sinatra, depending on your perspective. They did eventually venture out, exploring the city, drinking mojitos, and visiting the red-light district of La Playita by night. Gardner returned without him in later years, using the pseudonym Miss Grey, to reminisce about the good times. She was known to drink daiquiris for breakfast by the pool after nights out with Hemingway, which is the most Ava Gardner sentence ever written.
" There is something deeply romantic, and deeply sad, about returning alone to your honeymoon hotel. But Ava was never one for half measures.
After the Revolution in 1959, Castro converted the hotel into a dormitory for 900 peasant women who had come to Havana to learn to sew. The pool that had hosted Weissmuller and the Rat Pack was now the property of the revolution. It has since returned to hotel use. The Nacional has two outdoor pools surrounded by palm trees, with a poolside restaurant and a drinks service throughout the day, and rooms start from around $150 per night — making it by far the most affordable pool on the list, and arguably the one with the best stories.
Two outdoor pools surrounded by palm trees, with a poolside restaurant for lunch and a drinks service throughout the day. This is the pool Johnny Weissmuller reportedly impressed the staff with by jumping into from a second-floor window — the minimum expected, perhaps, from a man who played Tarzan for a living.
The on-site cabaret hosts nightly music and dance shows.
The hotel runs free guided tours of the grounds and its old military fortifications, taking you past the antique cannons of the Santa Clara Battery, now part of a UNESCO World Heritage Site.
A gloriously low-key tribute to the hotel's past, the Film Corner snack bar features a gallery of old Hollywood star portraits.
The hotel's famous terrace has arguably the best sunset views in Havana.
From the archives
From the Neptune Pool at Hearst Castle to the cabanas of the Beverly Hills Hotel, discover the iconic swimming pools where Hollywood's elite lounged, schemed, and made history.
26 hotels with genuine old Hollywood pedigree — from the Beverly Hills Hotel to Raffles Singapore — still taking reservations, still serving martinis, and still trading on golden-age glamour.