Spotlight: Tailored Stay Adds a New Level of Customer Care to the Vacation Rental Industry

Tailored Stay Adds a New Level of Customer Care to the Vacation Rental Industry

The travel industry has been hit hard by the pandemic. But there are still some who want or need to stay in vacation rentals throughout the country. And those consumers may prefer a personalized experience when they arrive.

Luckily, that’s exactly what Tailored Stay provides. More specifically, the concierge service provides grocery delivery, pre-made dinners, and even holiday services. Read more about the idea and the company’s journey in this week’s Small Business Spotlight.

What the Business Does

Prepares vacation rentals for guests.

Founder and President Kristin Fitzgerald told Small Business Trends, “We aim to take the stress out of vacation arrival by placing groceries and celebration items in vacation rental homes BEFORE the guests arrive.”

Business Niche

Providing convenient service.

Fitzgerald says, “By securing partnerships with top vacation rental property management companies we are able to gain access to the units, differentiating us from many other grocery services. We have received great testimonials for having provided memorable and safe vacation experiences in remote destinations this year.”

How the Business Got Started

After wishing for a similar service.

Fitzgerald explains, “The concept of Tailored Stay came separately to two of our founders. Tera Bennett was looking to have Birthday balloons, cupcakes and champagne placed in her Airbnb prior to arrival. She spent hours on the phone to achieve this and thought, ‘Wouldn’t it be great if there was a service that did this?’

At the same time, Fitzgerald and her husband Stephen arrived in Paris late at night. And they struggled to find an open grocery store to get basic late night meal and breakfast items. Because of that, they wished there was a service they could pay to make it easier on them.

Biggest Win

Creating valuable partnerships.

Fitzgerald says, “Hospitality is ultimately about people. And without working together on the shared goal of exceptional guest experiences, we wouldn’t get the word out as readily or build trust as fast as we have in Northern New Mexico.”

Biggest Risk

Launching in a remote area of New Mexico.

Fitzgerald explains, “None of our original founders live in the area. We were able to find wonderful personnel who truly care about hospitality to execute on the ground. Without them we could have suffered in product and delivery. At the same time, we offer over 6K items on our website. Without our wonderful IT staff, that could have looked more like 60. And we would have had very limited offerings.”

Biggest Challenge


Fitzgerald adds, “There were some on our team who were ready to fold. But through true grit and hope we were able to prevail. We stayed afloat by delivering locally (not our original business model) and by ensuring potential vacation guests, who would drive from neighboring states that we could help them more ‘safely’ vacation.”

How They’d Spend an Extra $100,000

Expand technology and service area.

Fitzgerald says, “Our technology could use some work in terms of speed and user experience. We would also expand operations to multiple beach locations so more vacationers could experience stress-free vacation arrival through the services of Tailored Stay.”

Team Tradition

Virtual meetings.

Fitzgerald explains, “We meet virtually every Wednesday and usually open up with a funny tidbit about the hard work of being a startup and close the meeting with a cheers and glass of wine to celebrate accomplishments big and small.”

Favorite Quote

“Traveling—it leaves you speechless, then turns you into a storyteller.” ? Ibn Battuta

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Find out more about the Small Biz Spotlight program

Image: Tailored Stay; Top Image: Kristin Fitzgerald, Tera Bennett, Stephen Fitzgerald, Nicholas Armstrong, Anna Arrow, Mark Dominic Grosso

Annie Pilon Annie Pilon is a Senior Staff Writer for Small Business Trends and has been a member of the team for 12 years. Annie covers feature stories, community news and in-depth, expert-based guides. She has a bachelor’s degree from Columbia College Chicago in Journalism and Marketing Communications.