The company is offering at least a $200 token to go towards products such as the Surface RT and the Surface Pro.
Microsoft is far behind Apple in terms of global tablet sales and market share.
One US-based analyst expressed doubts that many people would swap their iPad for a Microsoft product.
“Do I think that many people will take [Microsoft] up on this offer? In a word, no,” said Gartner mobile device analyst Van Baker. “The app ecosystem is the problem for Microsoft and this offer doesn’t fix that problem.”
There was a far greater range of mobile apps available for iPads than for Windows devices, giving Apple a competitive edge, said Mr Baker.
Microsoft has been engaged in an aggressive US marketing campaign to try to tempt Apple iPad users to buy Windows-based tablets.
In May, Microsoft launched an iPad v Windows comparison website, coupled with head-to-head advertising campaigns.
Microsoft has experienced problems trying to sell Surface devices.
In the first quarter of this year, Apple shipped 19.5 million iPads, compared with 900,000 Microsoft tablets.
In the second quarter, Microsoft shipped only 300,000 Surface devices, technology publication CiteWorld said.
Although Microsoft announced a revenue of $853 million on Surface sales in its latest financial regulatory filing, the company took a $900 million loss after failing to shift Surface RT devices.
Microsoft’s $200 (£150) gift certificate offer is valid in its bricks and mortar stores. A Surface RT tablet costs $349, and a Surface Pro retails at $799.