Condado Vanderbilt

'This legendary beachfront icon has been San Juan's crown jewel since 1919, where old-world elegance meets tropical sophistication on pristine Condado Beach.' What's Special? The hotel's Spanish Revival architecture features hand-painted tiles and mahogany furnishings original to the property. As Puerto Rico's first luxury resort, it hosted legendary guests like Frank Sinatra and Rita Hayworth. The oceanfront Serafina Beach Club offers exclusive access to one of San Juan's most coveted stretches of sand, while the rooftop pool provides stunning views of the Atlantic and historic Old San Juan. Don't Miss The world-famous Shanty Bar, an intimate tiki-style lounge that's been a local institution since the 1950s. Walk to historic Old San Juan (15 minutes) to explore El Morro fortress and colorful colonial streets, or catch the sunset at nearby Parque de las Palomas where hundreds of pigeons create a magical evening spectacle.