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The Story Behind Tailored Stay

It’s All About Arrival

Tera Bennett knows the value of a first impression. That’s why she spent hours on the phone trying to source someone who would put pre-arrival balloons and champagne in the vacation rental home she booked for her best friend’s birthday. ” I can’t find anyone who will make sure the things I want are in the unit when I get there. I wish there was a service that offered this,” she thought. A few days later when sitting around a table drinking wine with friends, she voiced this out loud. On that day, Tailored Stay was born.

With an emphasis on elevated guest experiences, Tera thrives in the role of Founder and Chief Creative Officer at Tailored Stay. “There’s nothing I love more than simplicity, elegance, and a thoughtful personal touch. Especially when I’m staying at a home away from home.”

Tera puts a critical eye on everything that passes through Tailored Stay. She’s focused on ensuring that guests have an easy way to order an arrival experience that they can’t find anywhere else. “My goal is to WOW our customers when they walk through the door,” she says. ‘For the guests, It should be as easy as showing up’.

There’s Got to Be a Better way

Kristin Fitzgerald has spent a few jet-lagged evenings with her husband looking for grocery stores in foreign cities.
“The first thing we always do after we arrive is stock up on essentials,” she says, “but the last time we traveled the thought occurred to us about how great it would be to have a bottle of wine, cheese, crackers and breakfast items waiting when we checked in.”

Kristin had similar thoughts when traveling with kids and family. “I have a sister whose family has special dietary needs. We always need to find a place with a kitchen and cook meals from scratch.” A novice chef herself, Kristin appreciates the option of being able to cook when
vacationing at a home rental property. She loves the idea that basic pantry and refrigerated items could already be there when a guest arrives.

As the President and Co-Founder of Tailored Stay, Kristin’s message is simple. “Let us take care of essentials so guests have the time to enjoy their stay and experience all their destination has to offer.”


How did you get all this in the kitchen before we got here?

Tailored Stay, of course!


What We Value



Saving you time to spend with loved ones instead of at the store while on vacation.


We work closely with owners to help them provide the best stay experience possible.


We’re vacation rental fans, and we know what is important to guests.

Quality over quantity

You can’t buy everything on TailoredStay, but what you can buy, we stand behind 100%. 

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