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The best holiday villas in Greece

After the year of social distancing, 2021 will be the time to reunite the generations and reach out to family and loved ones from whom we have been separated for too long. While we often feel like we need an excuse like a big birthday or a wedding to organise a multi-generational trip, in the years to come we will no doubt celebrate the simple pleasure of being able to get together once more.

Five Star Greece has been representing Greece’s most distinguished properties for over 18 years. The expert and highly motivated team of six, based in London, Athens and Brussels, have an enviable record of sourcing the right location for families and groups who want to create a memorable holiday experience – whether it is a large villa, a small hotel or a yacht.

The advisors will carefully listen to your brief, suggest things you may not have thought of based on their unrivalled knowledge and love of Greece and its islands and then wrap guests up in all the luxury they need, with help at every step of the way. From authentic local experiences, sports, gastronomy and sightseeing, to boating, helicopter safaris, massages or a Greek party with bouzouki and dancing, if you give them enough notice, they can arrange most things.

The ultimate way to enjoy a large group holiday in Greece is to rent out a holiday villa. Here are the team’s personal choices for 2021 family holidays.

Danae von Hirsch: Paros DY

Paros DY sleeps 22 in equal style and comfort with great outdoor spaces in the sought-after area of Santa Maria, with its family-friendly sandy beaches and the nearby bars, boutiques and waterfront restaurants of the beautiful port of Naoussa. Its configuration of two separate villas allows groups to retreat into privacy. Five Star Greece’s Paros concierge is dedicated to helping groups explore the island in style.

The firepit terrace at Paros DY
Paros DY

Dimitris Kaganis: Skiathos 1L

With a fabulous pool, beautiful views, lush gardens, its own sandy beach, excellent staff and a main house with a scattering of cottages surrounding, this property enjoys a high number of repeat clients and is ideally suited to a large family group. Skiathos has its own airport and is famed for its beautiful beaches and its lively, easy town where youngsters can roam freely.

Beachfront villa, Skiathos 1L on the island of Skiathos
Skiathos 1L

Titos Siopoulos: Villa Skinos

Make the odyssey to the beautiful and unspoiled island of Ithaca, where calm, peacock-coloured waters lap white stone beaches backed by cliffs and a few small fishing villages provide local colour and the authentic Greek island experience. A surprisingly large number of the Greek-Australian diaspora stem from this island, so in summer there is a real home-away-from-home feeling. For large families, Villa Skinos – with its main house and separate cottages, comfortably furnished beach, Skinos yacht, water sports on tap, full staff and over 160 hectares of land – has a fantastic track record.

Villa Skinos
Villa Skinos

Ileana von Hirsch: Kilada PRS

An easy drive from Athens, this is a very special property on a lovely stretch of unspoiled coastline, the so-called “Gold Coast of Greece”. The stone towers and collonaded terraces of this eight-bedroom villa echo the medieval glory days of this region. The villa is set in splendid grounds thick with lavender and rosemary and dotted with olive, pomegranate and citrus trees. Stone steps lead down to a tranquil and unspoiled beach.

Guests can take a boat from the property’s dock on a day cruise or to the elegant and car-free island of Spetses. The hinterland also has rich offerings: a spa at the nearby Amanzoe hotel, a visit to the ancient theatre of Epidaurus, the ruins of Mycenae and the 19th-century town of Nafplio are all within driving distance. The Peloponnese is also home to some very good wineries and artisanal food producers, so gastronomic tours, as well as cultural ones, can all be arranged.

Kilada PRS on its secluded peninsular
Kilada PRS

Maria Spanoudak: Crete Beach House

From Crete myself, I recommended heading to Crete Beach House to enjoy each other’s company and nature. In June, guests can watch the spectacle of turtles coming up onto the beach to lay their eggs and the hatchlings making their arduous way down to the water a few weeks later. For those wanting more social life and five-star services all-included, try Crete 1C, in the heart of Elounda with a private swimming jetty, experienced staff and fabulous views.

Beach toys for guests of Crete Beach House
Crete Beach House

Alex Staikos: Mani HNG

A large property spread over several beautiful houses and with a yurt on the garden for the occasional overflow, the owner of Mani HNG is an English historian who specialises in this fascinating corner at the southernmost tip of Greece and takes interested clients on tours to view the splendour of classical and byzantine Greece. Order his wonderfully readable trilogy called The Chronicles of Mistra – a rip-roaring historical yarn set in the last days of the Byzantine empire.

To make an enquiry, email

Mani HNG seen from the pool
Mani HNG

This article was produced with content supplied by Five Star Greece and is a Signature Luxury Travel & Style digital exclusive. Be the first to see more exclusive online content by subscribing to the enewsletter here.

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