TravelStaytion founder and MD, Jason Anastasinis

STRz spotlight: TravelStaytion founder Jason Anastasinis

UK / Greece: Jason Anastasinis, founder and MD of holiday rental platform TravelStaytion, speaks to STRz about the recovery of the Greek holiday rental market since the 2008 financial crash, the impact of the EU short-term rental initiative, and his vision for the company’s future.

  • Please introduce yourself, TravelStaytion and the services you provide in the short-term rental industry.

TravelStaytion is a collection of quality properties composed of intelligent technology, a community of professional property owners, local support and standards, curated to offer exceptional stays to every guest. Our mission is to create memories through elevated stays.

We work in partnership with professional property managers and owners to offer the most sought-after and curated spaces on the market. Our services allow property owners to achieve the ultimate stay status by getting better reviews, bigger revenues, and repeat visitors. This, in turn, provides a consistent and professional platform for our guests, driven by value and quality, with no unwelcome surprises.

Our high standards in service and systems elevate how guests experience stays, and ultimately, destinations. We have over 90,000 properties worldwide, with stays created through connections to professional property owners who have a better way to manage stays.

  • Tell us about your background – what brought you into the short-term rental market originally?

I grew up in Greece and have always had a deep passion for travel. I came to London in 2008 to complete my Masters, and when I graduated, I saw an opportunity to explore the short-term rental market.

The reality is I launched my career during the financial crash of 2008, when the tough economic situation was inspiring property owners to maximise their income from their assets. Add that to the growing trend of British travellers buying and choosing villas and apartments over hotels for holidays, I saw an opportunity to bridge the gap between traditional real estate and the travel industry using technology.

That’s where TravelStaytion enters the picture. I understood that property owners needed a consistent and high-quality holiday rental experience, something that individual owners couldn’t achieve without expert help. And even though I had no prior tech experience, I knew that technology was key to enabling property managers to deliver the quality standards that guests increasingly expect.

That’s why in 2012, we launched TravelStaytion.

  • How does TravelStaytion set itself apart from competitors in the intersection between hotels and short-term rentals?

We’re in the business of hosting, and it’s more than just a passion for us. We treat every stay as a unique experience that sets up our guests’ days for the better.

At TravelStaytion, there is real knowledge and expertise behind how we’ve created a new standard in stay. We’re travellers first, which means we prioritise our guests’ needs above all else, and we work in partnership with our community of professional property managers and owners to offer the most sought-after and curated spaces on the market, which allows us to bring the professionalism and experience of a hotel to holiday rentals. Moreover, technology is what makes the high standards of stay possible at scale.

Our guests’ stay is our measure of success, technology underpins everything we do.

The intersection between being traveller-first, community centric and technology-led is where we differentiate ourselves from competitor short-term rental companies.

  • How has the Greek holiday rental / real estate market evolved since the property crash of 2008?

Prior to the property crash, the market was booming, with foreign investors flocking to the country to purchase properties, particularly in popular tourist destinations such as Athens, Mykonos, Santorini and Crete.

Post-2008, the Greek real estate market and construction, in general, took a significant hit. Property values plummeted, and many investors faced significant losses. That said, despite the challenging economic conditions, the Greek holiday rental market remained resilient.

Travellers continued to visit the country, attracted by its rich history, culture, and natural beauty. Many property owners also began to offer their properties as holiday rentals to generate additional income, which helped to sustain the market.

The Greek government also introduced policies to encourage foreign investment in the real estate market, such as offering residence permits to non-European Union citizens who invested in property worth over €250,000.

As a result, since 2008, the Greek real estate market has shown signs of recovery, particularly in the holiday rental sector, due to a number of factors:

● Lower property prices following the financial crisis

● As tourism remained stable in Greece, there was an increased demand for holiday rentals

● The Greek government has invested in infrastructure developments, such as improving roads, airports, and public transport, making it easier for travellers to access popular destinations

● The introduction of new policies to attract foreign investors, such as reducing property taxes and offering a tax exemption on income earned from short-term rentals

● Diversification of the market, with investors looking beyond traditional holiday destinations to areas such as Kea, Crete and Rhodes.

  • How has the evolution of the holiday rental market impacted the local economy and communities?

The evolution of the holiday rental market in Greece has had a positive impact on the local economy and communities. The holiday rental market has contributed significantly to the local economy, creating jobs in areas such as property management, cleaning, and maintenance, providing income for local residents.

It has benefitted the local real estate sector at large, with significant investment being directed toward projects intimately linked with tourism and holidays, and it has also generated income for property owners, who can use the revenue to improve their properties, invest in local businesses, and support the local economy.

Additionally, the holiday rental market has helped to spread tourism beyond traditional destinations, bringing visitors to lesser-known areas of Greece and providing a boost to local businesses such as restaurants, shops, and tour operators. This has helped to create a more diverse and sustainable tourism industry in Greece.

  • Are there any specific challenges or opportunities that you have observed in the Greek holiday rental market in recent years? 

While there are challenges to the Greek holiday rental market, we believe there are opportunities for property owners and investors who can adapt to changing market conditions and meet the evolving needs of guests:


● Covid-19 pandemic: The pandemic resulted in a decrease in tourism, with many properties left vacant or operating at reduced capacity.

● Increasing competition: The growing popularity of holiday rentals in Greece led to increasing competition among property owners, putting pressure on rental prices and making it more difficult for property owners to attract guests.


● Growing demand for sustainable tourism: Owners who can offer eco-friendly and socially responsible experiences will benefit from this demand.

● Domestic tourism: International travel restrictions have led to an increase in domestic tourism in Greece, creating chances for owners to attract local guests and promote properties to a wider audience.

● Technology: Online booking platforms are making it easier for property owners to promote their rentals and connect with potential guests, thereby helping to increase occupancy rates and generate more revenue.

● Investment opportunities: The Greek government continues to offer incentives for foreign investment in the real estate market, which presents opportunities for investors looking to purchase properties in Greece.

  • What do these changes in the Greek holiday rental market mean for TravelStaytion?

Our strong presence in Greece and deep knowledge of the Greek holiday rental market positions TravelStaytion to take advantage of the opportunities and move in tune with the evolving Greek holiday rental market.

To cater to the diverse needs and interests of guests, TravelStaytion has expanded its portfolio beyond traditional holiday destinations to include properties in lesser-known areas of Greece that offer unique experiences.

The company has also integrated with online booking platforms and other technologies to make it easier for guests to find and book properties and for property owners to manage their rentals more efficiently. As a result, TravelStaytion has become a significant player in the Greek market, helping to highlight the country’s offerings on a global scale and adding value to the industry.

All in all, we are optimistic about the future of the Greek holiday rental market. Greece has a rich culture and is gaining a growing reputation as a sustainable tourism destination.

  • How do you anticipate the threat of regulations affecting TravelStaytion’s business e.g. from the Greek government or the proposed European Commission short-term rental initiative?

The short-term rental industry in Greece and the EU is subject to complex and ever-changing regulations. As a company, however, we understand the importance of staying up to date with the latest regulations and compliance requirements to ensure our operations are legal and ethical.

While the proposed European Commission short-term rental initiative may have an impact on the industry, I believe it to be a positive one, and our strategic approach is to work with professionals who comply with local authorities and EU regulations.

We aren’t particularly concerned about any specific regulations in Greece or the EU as we have already implemented country regulations as standard. The company’s compliance approach involves obtaining necessary licences and registrations, such as registration with the Greek National Tourism Organisation [GNTO] and obtaining all necessary licences and registrations in other countries where it operates.

Overall, while the regulatory landscape in Greece and the EU is complex, TravelStaytion is committed to ensuring that its operations are legal and ethical. The company is taking proactive steps to stay compliant with existing regulations and will continue to adapt its operations as necessary to ensure compliance with any new regulations as they arise.

  • How has TravelStaytion been able to emerge from the pandemic and are there any innovations you have implemented as a result?

Our focus on the traveller experience and exceptional stays from the outset has allowed us to emerge from the pandemic stronger than ever. We aim to capitalise on the whole booking experience from A-Z and ensure that our customers have an exceptional experience from the minute they click on the search field on our website until the very last minute they stay in our properties.

During the pandemic, we observed 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. We have also noted a growing trend that travellers use, on average, six to seven filters per search, with a strong preference for amenities. In response to this, we have given priority to properties with strong and unique amenities in searches by increasing the number of times they appear and placing greater emphasis on all of the benefits the property has to offer.

Moreover, as lockdown restrictions eased yet hygiene standards remained paramount, we also observed increased demand for the privacy that holiday rentals provide. Guests also wanted a more standardised experience with holiday rentals and increased demand for privacy when booking holidays. At TravelStaytion, we are equipped to cater to all these demands.

  • What is your vision for TravelStaytion?

My vision for TravelStaytion is to establish the company as the global leader in the holiday rental market through our commitment to quality standards and innovation in technology.

Looking forward, we see several areas of opportunity to capitalise on in the next five years.​

Firstly, the vacation rental industry is growing fast, and we intend to capture this opportunity by continuing to expand our portfolio of properties and enhance our services to meet the evolving needs of travellers.

Secondly, we plan to expand into new and emerging markets such as LATAM, which will help us diversify our offerings and tap into new customer segments.

Thirdly, we also see an opportunity in sustainability, which is becoming an increasingly critical issue for travellers. We want to lead the way in promoting and helping our property management community to provide better and more eco-friendly practices and services and hold them to higher standards.

We will continue to focus on innovation, quality standards, and meeting the evolving needs of our customers, and are confident in our ability to innovate and deliver on our vision to transform the holiday rental market.

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