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Authorities allowed residents into the first area to be cleared for re-entry, a zone of about two dozen parcels in the northern part of Lahaina, between 8am and 4pm.
The August 8 wildfire killed at least 97 people and destroyed more than 2,000 buildings, most of them homes.
Officials urged residents not to sift through the ashes for fear of raising toxic dust.
The prospect of returning has stirred strong emotions in residents who fled in vehicles or on foot as the wind-whipped flames raced across Lahaina, the historic capital of the former Hawaiian kingdom, and overcame people stuck in traffic trying to escape.
Some survivors jumped over a sea wall and sheltered in the waves as hot black smoke blotted out the sun.
From a National Guard blockade near the burn zone, Jes Claydon has been able to see the ruins of the rental home where she lived for 13 years and raised three children.
Little remains recognisable beyond the jars of sea glass that stood outside the front door.
Ms Claydon hoped to collect those jars and any other mementos she might find.
“I want the freedom to just be there and absorb what happened,” she said.
“Whatever I might find, even if it’s just those jars of sea glass, I’m looking forward to taking it. It’s a piece of home.”
Her home was a single-storey cinderblock house painted a reddish colour, similar to the red dirt in Lahaina. A few of the walls are still standing, and some green lawn remains, she said.
Authorities have divided the burned area into 17 zones and dozens of sub-zones.
Residents or property owners of the first to be cleared for reentry were being allowed to return on supervised visits on Monday and Tuesday.
Darryl Oliveira, interim administrator of the Maui Emergency Management Agency, said officials also want to ensure they have the space and privacy to reflect or grieve as they see fit.
“They anticipate some people will only want to go for a very short period of time, a few minutes to say goodbye in a way to their property,” Hawaii governor Josh Green said last week.
“Others may want to stay several hours. They’re going to be very accommodating.”
Those returning were being given water, shade, washing stations, portable toilets, medical and mental health care, and transportation assistance if needed.
Non-profit groups also offered personal protective equipment, including masks and overalls.
Officials have warned ash could contain asbestos, lead, arsenic or other toxins.
