Rooms have to be found for dozens of Secret Service agents, someone has to carry a selection of presidential basketballs, and of course the family dog needs his own state-of-the-art aircraft.
Bo, the president's Portuguese Water Dog, arrived separately on one of two MV-22 Ospreys, a hybrid aircraft which takes off like a helicopter but flies like a plane.
It was the first time the Ospreys have been taken on holiday by a US president.
More than 70 hotel rooms, each costing up to $345 (£220) a night, have been booked out for Secret Service agents, who took charge of luggage including two large mesh bags full of basketballs.
The Obamas are staying in Chilmark on the western tip of the island, an area that is dotted with multi-million dollar homes. The neighbours include actor Ted Danson and the singer Carly Simon.
On several previous visits the Obamas had stayed at the 28-acre Blue Heron Farm, but it has since been sold to Britain's most celebrated architect, Baron Foster of Thames Bank.
The president has therefore had to downsize to a $7.6 million, 5,000-square foot retreat on nine acres which is owned by a businessman friend from Chicago. It includes a basketball court.
As a result Mr Obama will be staying closer to public roads which will have to be closed as his motorcade heads for the golf course of bookshop.
The Martha's Vineyard Times newspaper warned residents to expect "extraordinary and lengthy up-island detours". Local officials also emailed residents, saying: "Anyone aggrieved by this closing should email or call the White House."