Tailored Stay

Travel thoughtfully when you pre-order all your vacation rental nee...


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Tailored Stay Overview

Tailored Stay is a turn-key solution providing curated concierge services for vacation rental guests, including online groceries, beverages and celebration packages. Guests pre-order on one easy to use platform and all items are in the unit upon arrival.

Tailored Stay saves time and stress while enhancing the vacation experience by ensuring that guests arrive to a fully-stocked rental, increasing their satisfaction and bringing more business to local retailers and property managers.

One Extra Step...

Picture this: You’ve arrived at your vacation destination, after a long flight or stressful drive. You find all the beautiful property amenities you need including a fully-equipped kitchen.

Unfortunately, the fridge is bare. Kids and friends are begging to go to the pool, trails or lake while you begrudgingly search for the nearest grocery store. And let’s be honest, most of us aren’t exactly thrilled to spend their precious vacation time waiting in line at the local Walmart.

Now there is an alternative. For those of us who desire the simple convenience of a fully-stocked kitchen and celebration items at our vacation rental, there’s Tailored Stay.

Convenience At Your Fingertips

With Tailored Stay, you can quickly and easily pre-order all your groceries, beverages and even personalized celebration packages and have them delivered and arranged in your vacation rental, all before you arrive.

That means no more standing in lines after a long day of travel. No more debating what you can or can’t fit in your carry on. No more last-minute trips to the drug store or supermarket. Instead, you can dive into your vacation straight away!

Tailored Stay’s team of dedicated Vacation Tailors are motivated to deliver top-notch hospitality. Whether you need a few groceries or are gearing up for a family reunion or wedding, they offer just the right services you need to have the added convenience to enjoy a memorable vacation.

How It Works

Tailored Stay makes it easy to plan for meals and celebration supplies weeks or even months before your vacation. Stress less and start enjoying your vacation the moment you step through the door. Simply:

Tailored Stay covers all the bases so you can can shop for what you need, pay at checkout and have your items delivered just hours before you arrive, all on one platform.

Tailored Stay has partnered with local retailers to give you a comprehensive ecommerce experience. They also work with property managers for temporary access to your rental, so they can stock your place with everything you need to get your vacation started right.

Trailblazing Success

Tailored Stay has a fully-developed website and e-commerce engine with back-end integrations to grocery and other retailers systems and processes. They have several existing relationships with property management companies.

Now moving into post beta phase, Tailored Stay is concluding their operational pilot program in Red River and Angel Fire, NM while ramping up in Lake Geneva, WI. During their 2-year pilot in NM, they have fulfilled and collected valuable operational data on 150+ unique vacation customer orders.

Wins And Testimonials

Tailored Stay has gained some PR and loyal advocates while in the beta phase. Most notably seen here: https://smallbiztrends.com/2021/01/tailored-stay-business-feature.html


And more!

Our Founding Story

Tailored Stay started out as the simple solution to a problem that many people, including our founders, have encountered on their getaways.

Founders Kristin and Stephen Fitzgerald had the frustrating experience of arriving late at their vacation rental homes in Paris. Not able to speak the language, they had to find an open grocery store for basic items. At one point, Kristin turned to Stephen and said, ‘I would have paid to have basic items stocked here’.

Just a few short weeks later they met with Founder Tera Bennett who had spent hours on the phone trying to get a Nashville vacation rental stocked with champagne, balloons and cupcakes for her best friend’s Birthday.

Over a conversation about their mutual love of travel, hospitality, great food and wine, that evening, Tailored Stay was born.

Today, having proven the concept on a small scale and tested scalability, Tailored Stay is ready to expand to a destination near you!

The Tailored Stay Team

Kristin Fitzgerald, CEO | Kristin is the head lead as well as the brand and product leader, She spent 10 years in digital marketing before founding Tailored Stay.

Stephen Fitzgerald, CFO | Stephen is the primary funding source. He has held SVP and VP level positions at major hotel chains and travel distributors. 

Nicholas Armstrong, CTO | Nicholas brings a 25-year career in retail and healthcare IT infrastructure and technology stacks

Cecilia Cuff, Operations Director | Cecilia has a Hyatt hotels background and is a gifted entrepreneur with operations experience in restaurants and hospitality.

Mark Grosso, General Counsel | Mark is the former marketing leader at Verizon. He specializes in general civil and business law practice.

Pat Parker, Website Lead IT | Pat keeps things going. She has been in the IT business for the last 25-years, dedicating the last 12 specifically to WooCommerce and WordPress sites.

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