Surf Side Cottages began as "Surf Side Colony," a community of seaside, Cape Cod cottages in South Wellfleet in the late 1940's and early 1950's. This cottage colony had a number of owners over the years, and in 2005, they were sold as condominiums. This means that each cottage now has a different owner, but they all are still available for rent to individuals and families looking to stay in a cottage by the sea.

Armand and Lisa Audette founded "Blue Sky Property Management" in 2008, after successfully managing (and owning) The Even'tide Resort Motel and Cottages, also in South Wellfleet. With a combined 62 years of hospitality experience on Cape Cod, they know how to treat the Cape Cod visitor. This is attested to by the many positive comments and reviews they've received and by their winning "Top Rental Manager, 2011" by FlipKey.com, an online rating company.