Sandpiper grows faster with MyLodgeTax Pro + Streamline VRS

Sandpiper Management is a vacation rental company based in Seabrook Island, South Carolina. In 2021, Tony Napolitano and his wife partnered with a family member to take over and grow the business. What began as a traditional property management and cleaning company evolved into a full-service short-term rental business focused on delivering professional hospitality and peace of mind to homeowners.

“We decided to go all-in on rentals,” Tony says. “We phased out the management side entirely and focused on building a true vacation rental business.”

As Sandpiper CFO, Tony manages accounting and finance and turned to Avalara as tax requirements grew. “Once we started growing, we knew we needed a better way to handle tax compliance,” he explains. “That’s when we adopted Streamline and Avalara.”

Before partnering with Avalara, Tony managed tax compliance manually, a time-consuming and error-prone process. “Every month, I’d go through each reservation, calculate the correct state, county, and local taxes, and then submit returns for every homeowner,” he explains. “In South Carolina, some jurisdictions still require paper coupons to be mailed in. It felt like doing taxes in the 1960s.”

The increasing number of rental properties only magnified the challenge. Managing 60 properties across multiple jurisdictions meant tracking constantly changing tax rates, filing schedules, and remittance rules, often varying by city or county.

Adding to the complexity were the evolving tax policies of marketplaces like Airbnb and Vrbo.

“One month they’re filing state tax, the next they’re not filing county or local taxes. It’s constantly changing,” Tony says. “Staying on top of it all was becoming a full-time job and I already had one.”

Manually managing these variables created risk and limited Sandpiper’s ability to scale. Tony needed a way to offload the burden of compliance so he could focus on growing the business.

As Sandpiper transitioned into a dedicated short-term rental business, the need to automate tax compliance became increasingly urgent. Tony evaluated Avalara MyLodgeTax Pro and quickly saw how it could reduce complexity and free up time for growth.

“Avalara’s offering stood out right away,” Tony says. “From the start, it was clear the solution was designed specifically for short-term rental businesses like ours. I wasn’t looking for a one-size-fits-all tool, I needed something that truly understood the tax challenges we face.”

Although Sandpiper was already using Streamline for property management, the decision to choose Avalara wasn’t based solely on the integration. “We chose Avalara for the functionality and support, even before it was integrated with Streamline. Once that integration became available, it just made everything that much easier.”

Tony was also impressed by Avalara’s ability to take ownership of the tax process. “The biggest value was knowing I wouldn’t have to manage the filings myself. That meant less stress, fewer errors, and more time to grow the business.”