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Luxury villa holidays in Greece

Once synonymous with family-run pensions and simple rooms to rent, Greece now offers some of the finest luxury villa holidays in the Mediterranean. The heart-felt hospitality, rich history and seemingly endless summers are still here, but today you’ll also find stunning contemporary accommodation with private pools, perfect for families and couples.

The Mediterranean holidays with more choice

With deep gorges and snow-capped peaks, pristine sandy beaches and gleaming white-pebble coves, the appeal of a villa holiday in Greece is as broad as the country’s astonishing history is long. From rural cottages to sleek seaside villas, the Simpson Travel luxury villa collection reflects this wonderful diversity, whilst incorporating the essentials of air-conditioning, wifi and a private pool in the vast majority of our properties.

Your guide to the Greek Islands

The larger islands such as Corfu, Crete, Lefkada, Zakynthos and Kefalonia offer the widest choice of villa holidays for families, couples or groups – and the most child-friendly beaches. On Zakynthos and Lefkada, you’ll find the renowned Simpson Travel Crèches & Children’s Clubs, whilst Sivota, Skopelos, Ithaca, Paxos, Kefalonia, Corfu and Crete offer a range of carefully chosen cottages and villas for two. For the slightly more adventurous, the smaller hideaways such as Paxos, Skopelos, Ithaca and Meganissi blend the charm of a classic Greek island escape with the luxury of a contemporary villa with its own private pool. And if island life is not your style, the pretty harbour town of Sivota gives you the chance to mix coast and the magnificent countryside of the interior.

So much choice can sometimes be a challenge, so if you’d like help narrowing down your personal selection, just get in touch with our Greece experts or explore our regional guides.

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Villa Vereniki

Chania & West Crete, Crete, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Beautiful sea views above Almyrida
  • Contemporary and stylish
  • Close to tavernas and sandy beach
  • Nearby to watersports and activities

Accommodation only available on Tuesday 18 October 2022 Call for price

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Blue Infinity

Sivota, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Stylish contemporary villa
  • Beautifully designed
  • Stunning sea views
  • Beach and restaurants 5min drive

Accommodation only available on Sunday 9 October 2022 Call for price

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Amalthia Cottage

Ithaca, Greece

Villa | Bedroom 1 | Sleeps 2

  • Simply Simpson
  • Romantic open-plan cottage
  • Private pool and garden
  • 5min drive to Vathy

Accommodation only available on Saturday 8 October 2022 Call for price

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Villa Aetos

Palekastro & Far East Crete, Crete, Greece

Villa | Bedroom 1 | Sleeps 2

  • Short walk to best beach in Crete
  • Set in unspoilt Xerokambos
  • Beautiful views
  • Tavernas and mini-market 5min drive

Accommodation only available on Tuesday 6 September 2022 Call for price

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Nafsika

Corfu, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Delightfully positioned villa
  • Spacious terraces
  • Spectacular sea views
  • Simpson family extras available

Accommodation only available on Sunday 16 October 2022 Call for price

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Villa Ekavi

Corfu, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Comfortable family villa
  • Stunning sea views
  • Spacious outside pool terrace
  • Simpson family extras available

Accommodation only available on Sunday 16 October 2022 Call for price

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Agni Cottage

Corfu, Greece

Villa | Bedroom 1 | Sleeps 2

  • Charming, romantic cottage
  • On Agni water's edge
  • Comfortable and cosy
  • Walking distance to tavernas

Accommodation only available on Wednesday 19 October 2022 Call for price

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The Stone House – Greece

Paxos, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Comfortable and charming house
  • Stunning 20m infinity pool
  • Delightful sea views
  • Spacious open-plan living area

Accommodation only available on Sunday 2 October 2022 Call for price

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The Artist's House

Paxos, Greece

Villa | Bedroom 1 | Sleeps 2

  • Romantic stone house
  • Ideally positioned overlooking the sea
  • Bright and comfortable
  • Beach 5min walk

Accommodation only available on Sunday 14 August 2022 Call for price

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Reviews

Simpson Travel in the media

  • ‘[Simpson Travel] specialise in the sort of magical, unspoilt destinations my family loves’ Author: The Telegraph

  • ‘So how did we find the near-perfection that was Villa Cabanellas in Mallorca? The first step was to approach… Simpson Travel… we needed expertise, not just blinding choice.’ Author: Sunday Times Travel Magazine, The Villas Handbook

  • ‘The Simpson Travel check-in at Heathrow’s Terminal 5 was seamless.’ Author: Family Traveller, Katy Hill

  • ‘Where Simpson [Exclusive] really excels is in its first-hand knowledge of properties and destinations’ Author: House & Garden

  • ‘Simpson [Exclusive] delivers holidays that combine sunshine, five-star luxury and friendly service’ Author: House & Garden

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Travel advice

For up-to-date advice and information on travel from the UK, including passports, visas and health and safety, please visit the Foreign Commonwealth & Development Office website or call 020 7008 1500. For travel from countries outside the UK, please visit your corresponding government website.

The air holidays and flights shown are ATOL protected by the Civil Aviation Authority. Our ATOL number is ATOL 5858. ATOL protection extends primarily to customers who book and pay in the United Kingdom. Find out more about ATOL. Simpson Travel is the trading name of Far & Wide Ltd.

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  • Destinations

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    France

    France

    • Provence
    • The Dordogne & South West
    • Vendée
    • Aquitaine Coast
    • Ile de Ré

    Mallorca

    Mallorca

    • Fornalutx & Sóller
    • Pollença & Puerto Pollença

    Greece

    Greece

    • Corfu
    • Crete
    • Ithaca
    • Kefalonia
    • Lefkada
    • Meganissi
    • Paxos
    • Sivota
    • Zakynthos

    Turkey

    Turkey

    • Akyaka
    • Bozburun Peninsula
    • Islamlar & Uzumlu
    • Kalkan
    • Kaş

    Italy

    Italy

    • Tuscany
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    Corsica

    Corsica

    • Calvi & The Balagne
    • Porto Vecchio & Bonifacio
    • The Valinco
  • Villas

    Villas

    • Villas with childcare
    • Luxury villas
    • Off the beaten track villas
    • Car-free villas
    • Large group villas
    • Villas together
    • Romantic villas for two
    • Family Favourite villas
    • Teen-friendly villas
    • Beachfront villas
    • Villas with heated pools
    • Villas near the beach
    • Villas near a restaurant

    Back

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    Back

  • Holiday inspiration

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    Holiday Types

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    • Couples holidays
    • Beach holidays
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    • Car-free holidays
    • Twin Centre holidays
    • 10-night holidays
    • Countryside holidays
    • Honeymoons
    • Babymoons
    • Special Interest Holidays
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    • Holidays with childcare
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    Collections

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    Our Blog

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