It was founded by Robert Munro, Reginald Collins and Jack Mines and began operations with a single Aeronca Model K seaplane and a hangar at a location formerly occupied by a lumber mill on north Lake Washington.

[6] Kenmore Air originally made its money by accessing remote and sometimes dangerous locations during its early years.

In July 1946, pilot Jack Mines was killed while flying supplies to a search and rescue team in the nearby Cascade mountains; as a result, Collins and Munro became the two owners of Kenmore Air.

[6][8] In the 1950s, Kenmore Air began its charter business by offering flights to fishing and hunting spots in the Pacific Northwest.

The aircraft flew in several pieces of large equipment to the glacier, including diesel engines, railroad cars, and tractors.

[6][8] In the 1960s, Kenmore Air expanded its maintenance services to include the de Havilland Canada DHC-2 Beaver seaplane.

[9] In the early 1970s, in a contract with the US Navy, Kenmore Air transported unarmed torpedoes to a joint US-Canadian testing facility near Vancouver Island.

In 1998, Kenmore Air gained a federal permit allowing them to begin operations there, pending approval from Seattle's city council.

[6] Residents in both Seattle near their Lake Union seaport[12] and in Victoria have been growing increasingly concerned about noise and safety on the water.

In Sept 2011 Victoria the St. James Community commissioned a report [13] that calls for "serious restrictions on seaplane businesses" (which include other services like helicopters).

Kenmore Air Express began twice daily service from Friday Harbor to Victoria International Airport in the city of Sidney.

[16] Kenmore Air Express provides daily, year-round service to the Washington communities of Eastsound and Friday Harbor.

Kenmore Air's livery also appears in Microsoft Flight Simulator X on the Cessna 208 Caravan and de Havilland Canada DHC-2 Beaver.