Old Havana (Habana Vieja)
Old Havana is the place to stay of choice for most tourists for its rich history and architecture. Habaguanex (the commercial wing of the Historian's Office) runs a number of charming smaller boutique hotels, although if you want more amenities and a pool try the Saratoga or Parque Central (which are located around Parque Central - see below). While Old Havana is the place to be during the day at night the restaurants and nightlife is disappointing with most bars closing early and the best paladares and clubs located elsewhere.
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Central Havana
Centro Habana' falls between the restored Old Havana and posh city suburbs further west and is for the most part relatively run-down. The significant exception is the area around Parque Central which while officially designated as part of Centro Habana is actually better seen as an adjunct of the Old City. There are some good restaurants (Nardos / La Guardia) as well as one of the best nightclubs (Casa de Musica Galliano), but don't expect too much during the day.
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Vedado
Vedado was the first real suburb of Havana and is home to many gorgeous mansions which add so much character to the city. As Havana expanded Vedado became much more central and now is mid-way (10 minute taxi ride) between the old city and the Western suburbs of Miramar / Playa. It is also home to the historic Nacional, Habana Libre (formerly Hilton) and Riviera Hotels as well as many of the best private restaurants in the city.
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Miramar and Playa
People on repeat visits or in Cuba on business often prefer to stay in Miramar, the business / diplomatic district, which has a number of large good value, good service hotels of which the pick is the Meliá Habana. There are also some great restaurants in this area and a number of good bars and clubs (although they are a little dispersed so transport is helpful).
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Havana
'Arguably Latin America's best-preserved city, Havana is one of the oldest, grandest and safest cities in the Americas, and packs a cultural punch well beyond its size [.] Havana glories in its history, has a dynamic cultural life and thrives on the gregarious personality of its inhabitants, 'los habaneros'. This is a city pulsing with energy that will sweep you up and hold you captive until long after you leave.'
Time Out Guide to Havana and Best of Cuba 2003