The San Francisco company's website said Sunday it had received a license from the US Treasury to "welcome guests from around the world to stay one of their 4,000 listings in Cuba."
The move, announced hours before Obama's arrival in Havana, represents the latest effort by his administration to chip away at decades of Cold War-era sanctions.
The Republican-controled Congress has refused to lift an embargo on Cuba, but Obama is betting that a host of incremental and seemingly technical steps will open Cuba's economy, transforming the communist-controled island economically and politically.
Obama's approach is a dramatic U-turn for the US government, which for decades tried to squeeze the Cuban government through sanctions.
"It's a soft war" said John Kavulich, president US-Cuba Trade and Economic Council, "using visitors as the soldiers, commercial airlines as the air force, and cruise ships as the navy."
On Saturday Starwood Hotels & Resorts announced it had signed three hotel deals in Cuba, a first for a US hospitality company since the 1959 revolution.
Until now, only American customers had been allowed to use the service.
Obama's visit is the first by a sitting US president since Calvin Coolidge arrived 88 years ago.
