Welcome to MyStay Hilton Head Island Vacations, where thoughtfully selected homes and genuine hospitality come together to create unforgettable Hilton Head vacations. Every home in our collection has its own personality, but they all share the same promise: comfort, quality, and a place you'll look forward to coming back to year after year.

Featured stays

Discover amazing places to stay

Stay Before the Year Ends

Trade the rush of the season for a quieter side of Hilton Head. Enjoy 5% off select stays through December 2026.

MySTAY

When we started MyStay Vacations, we weren't trying to become the biggest vacation rental company on Hilton Head, we simply wanted to be the kind of company we'd want to book with ourselves. One that communicates well, pays attention to the little things, and genuinely cares about every stay. That commitment still shapes every home we manage and every guest we welcome.


- Brian & Kristen

"No matter how 'prepared' you think you are or how much you 'know' the island... it was fantastic to be able to call and have someone immediately answer, literally every single time."

— The Robinsons

Experiences

Every detail is thoughtfully planned to create a Hilton Head stay that feels effortless, personal, and unforgettable.

Your Guide to Hilton Head Island

Villa & Resort Living

Our Private Homes