Seasonal Hilton Head Island Vacation Specials & Deals

When fall makes its way to the Lowcountry, you can always look forward to beautiful days on the sea islands. Whether you’re celebrating our area’s vibrant heritage at the Gullah Food Festival or enjoying the Lowcountry’s natural bounty at the Bluffton Arts & Seafood Festival, you’ll find so many reasons to pack your bags for an October getaway to Hilton Head. These October vacation specials are just the icing on the cake (or in our case, the butter on the cornbread!)
Remember to open your free 7-Day Vacation Guide for more incredible ways to enjoy fall on the island. We hope to see you soon!

With shorter minimum stays and lower rates, now is the perfect time of year to take advantage of long weekends, fall breaks and all of the festivities on Hilton Head Island!

View Discounted Properties

Live Like a Local when you visit in the off-season for a monthly visit. You will enjoy less crowded roads restaurants and beaches as well as highly discounted rates!

Featured Monthly Properties

Enjoy beautiful year-round weather and swing away when you book a weekly stay for a golf getaway this fall. One dozen Titleist Pro VI Golf Balls are on us!

Golf Course View Properties

Your home away from home for the Holidays!  Weekly reservations will receive a Publix Gift Card to prepare all of your familys favorites in our fully stocked kitchens!

Island Holiday Homes and Villas