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Meet the luxury travel expert: Jason Anastasinis, founder and MD of TravelStaytion

Ina Yulo Stuve talks to Anastasinis about using technology to deliver first-class guest experiences.

By Ina Yulo Stuve   |  

Technology has disrupted many an industry over the past few decades, and travel is one of them. Whether it’s reaching a younger customer base who depend on the Internet for booking their accommodations, to automating the logistical headaches associated with planning a trip, tech start-ups have changed the way we travel.

Leveraging technology to deliver a first-class experience to holiday bookers was exactly what founder and managing director Jason Anastasinis aimed to do when he launched TravelStaytion, the traveller-first, technology-led online holiday rental marketplace. “Our platform provides a number of easy-to-use tools to search and book memorable experiences quickly and easily, alongside other benefits such as options to split payments between friends,” he explains.

The platform also allows the team to better understand a guest’s preferences and travel needs and identifies properties and experiences that fit what they’re looking for.

When it comes to hosts, Anastasinis proudly shares that TravelStaytion’s model supports property owners in strategically positioning their properties in front of their target audience. “Technology is how we do this at scale,” he explains. “It allows us to create a platform for owners to achieve the ultimate stay status; getting better reviews, bigger revenues, and repeat visitors. It also gives property owners access to invaluable data and insights, tools, and guides, so they can continually deliver memorable experiences.”

Jason Anastasinis
Jason Anastasinis launched TravelStaytion, the traveller-first, technology-led online holiday rental marketplace

In a marketplace business, choosing who you include in your partnership network is integral to your company’s success. “We’ve always had a clear idea about who we want to work with – professionals who seek to provide a quality experience to guests,” says Anastasinis. “So far, we have focused particularly on growing our community of property owners and managers, and, in turn, our property portfolio in the UK, Italy, US, Spain and Greece. As we continue to grow, we want to continue to provide the same level of support to our community, which is why we’re focused on growing our local support networks in these countries at this time.”

LLM writer Ina Yulo Stuve chats with Anastasinis about changing customer behaviours post-pandemic and what makes a good host.

Did you always want to work in the travel industry? 

Growing up, I always had a passion for travel. However, it was only when I had completed my masters in London and had observed the opportunity for holiday rentals that I knew it was an avenue I had to explore initially. I wanted to provide property owners with income amidst the Greek property crisis, and also observed the trend that more Brits were choosing to stay in villas and apartments on holidays. I then recognised an opportunity to use technology to bridge the gap between traditional real estate and the travel industry. 

TravelStaytion was the first venture in my career. It was a start-up. I understood that greater consistency in the holiday rental experience was required, and I knew that this couldn’t be achieved by individual owners without the help of experts. So, although I had no prior tech experience, I understood that a platform to standardise the whole market was required to ensure guests could enjoy a great stay every time. I put my all into making it happen, I attended countless exhibitions to understand the market, I gathered a team and recruited the now CTO to help kickstart platform development, and in 2012 we launched TravelStaytion.

made by the sea villa pool
Made By The Sea Villas are located in the beautiful coastal town of Mades in Crete

If you had to describe TravelStaytion in three words, what would they be? 

Traveller-first – Our priority is putting our guests’ needs first, in the business of hospitality, every stay matters. Our guests’ stay is our measure of success.

Community-centric – Our trusted community of property managers are committed to providing a high quality, standardised, and consistent service. We work in partnership with property owners to offer the most sought-after and curated spaces on the market.

Technology-led – Technology is what makes the high standards of stay possible at scale. We see it as the true passport to creating a new standard in stay.

What were some of the obstacles you faced when scaling your business? 

When starting any new business, it’s normal to encounter obstacles. However, we stuck to our guns as we knew there was a gap in the market, and we had a clear vision of how to standardise both the booking and property management process for travellers, property owners and managers alike. At the start, there was resistance to change within the industry with some travel agents and tour operators not willing to cooperate. Then when it came to the competition, other competitors had already launched.

However, TravelStaytion offered something different, seeking to create a seamless experience for all involved in the holiday rental experience. Speaking of competitive environments, being in London can be a little intimidating for someone launching a start-up. But despite securing no initial funding, we received incubation space and support from Bayes School (formerly Cass Business School). This gave us the confidence and drive to grow TravelStaytion, enabling us to employ three people in London and another four in Greece.

made by the sea villa interior
Made By The Sea Villas provide a stylish and luxurious escape

What is your strategy for hiring and retaining talent? 

We have a clear vision here at TravelStaytion, which helps us attract incredible talent and workers that are passionate about tech and the travel space. We offer all staff continuous learning and development opportunities, as well as the chance to contribute to the growth of our company. Key benefits also include training and development programmes, flexible hours, health insurance, and more. We want our people to feel like they have a voice and that they can be heard. TravelStaytion aims to respond and improve as an organisation in line with our employees’ needs and thoughts.  

Are there any changes in customer behaviour that you’ve noticed since the pandemic? 

The pandemic allowed consumers to build up their savings. Now, despite the cost-of-living crisis and people looking to spend more wisely on certain things, we’re seeing that our customers are still willing to indulge. We’ve seen an increase in customers opting for higher budget, quality properties to capitalise on the amenities that a villa or an apartment can offer, such as outdoor areas, barbecues and private pools.

Having already familiarised themselves with holiday rentals, particularly when lockdown restrictions eased and hygiene standards were paramount, we also observed increased demand for a more standardised experience with holiday rentals, and an increased demand for privacy when booking holidays. TravelStaytion is equipped to cater to all of these demands.

What are some of the characteristics that all of your top hosts share?

Strong, local support networks and presence are a big part of our host network. Not only does that mean that there is often someone nearby who can promptly address any issues that arise during a guest’s stay, but it also means that guests can have a positive experience by providing them with recommendations on local attractions, restaurants, and activities.

A strong local presence also means property management is that bit more seamless. They can support with tasks such as cleaning and maintenance and it also means there are people there to support with bookings, help facilitate the check-in and check-out process, and handle any issues that arise with guests.

Guest-oriented services also play an integral part in TravelStaytion properties. For us, travellers’ stays are not just about the property, but also about the experiences offered to the guest. The stay is not just where guests sleep, but where the collective memories of their entire trip are made.

This could include offering guests’ amenities such as complimentary breakfasts, cleaning services, or providing them with access to a concierge service that can help them plan their itinerary and make reservations. In some instances, it could also mean offering guests unique and memorable experiences, such as spa treatments or guided tours in nearby areas. 

made by the sea villa views
Made By The Sea Villas have stunning ocean views and direct beach access

Where is your favourite place to go on holiday? 

Crete, Greece. It has pristine beaches, there is a rich gastronomic, historical, and cultural offering, including hundreds of ancient sites, breath-taking landscapes and hiking paths to explore. I feel it’s unique, which is what I seek in a destination. 

A particularly beautiful area of Crete, is Mades, a beautiful coastal town located just a 15-minute drive away from Heraklion, the largest city in Crete. It’s calmer and quieter than neighbouring towns, and has a stunning sandy beach. One of our holiday rental properties, Made By The Sea Villas, is in the perfect spot for travellers looking to stay in Mades. Located directly above the water, it offers stunning beachside views. There’s even a stretch of beach directly accessible from the villa itself. 

What’s next for TravelStaytion? 

Firstly, we’re looking to continue to expand our team. When we started out, there were just two of us, and now we have around 50 staff that make TravelStaytion what it is today. We want to grow by 50% in terms of headcount by the end of 2023. Secondly, we want to grow our property portfolio. Currently, we have roughly 85,000 properties on the platform.

As we look to the future, we aim to become the largest provider of quality stays, continuing to develop innovative technology, offering more tools to support property managers while building local presence and expertise. 

Factbox

TravelStaytion

Address: 26 Cadogan Square, London SW1X 0JP
Phone: 020 3624 0359
Website: travelstaytion.com
Instagram: instagram.com/travelstaytion