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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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Cedar Bay Beachside Villas – Lithos

Chania & West Crete, Crete, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Beautiful beachside villa in SW Crete
  • Adult only
  • Stylish and contemporary
  • Taverna 5-minute walk

Prices are based on 2 sharing for 7 nights on Tuesday 6 April 2021

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$1,384pp Total price $2,768
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Simply Simpson

The simple things in life often give the greatest pleasure and we believe our Simply Simpson Collection offers the chance to experience a more authentic taste of local living in some of the most idyllic locations in the Mediterranean. Take time to discover our comfortable, no-frills accommodation and join us on the road less travelled.
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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

Prices are based on 2 sharing for 7 nights on Sunday 9 May 2021

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$1,387pp Total price $2,774
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Villa Melia

Lefkada, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Stylish sea front villa
  • Beautiful sea views
  • Steps down to private pontoon
  • Walking distance to tavernas

Prices are based on 2 sharing for 7 nights on Sunday 2 May 2021

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$1,393pp Total price $2,785
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Villa Santolina

Lefkada, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Stylish contemporary villa
  • Beautiful views
  • Walking distance to sandy beach and tavernas
  • Simpson family extras

Prices are based on 2 sharing for 7 nights on Sunday 2 May 2021

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$1,393pp Total price $2,785
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Villa Taphian

Meganissi, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Stylish contemporary villa
  • Finished to a high spec
  • Spacious terrace with barbecue
  • Waterside tavernas at Vathy 5min walk

Prices are based on 2 sharing for 7 nights on Sunday 2 May 2021

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$1,396pp Total price $2,791
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Neritos House

Ithaca, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Comfortable welcoming house
  • Stunning sea and mountain views
  • Light and airy
  • Vathy shops and restaurants 5min drive

Prices are based on 2 sharing for 7 nights on Saturday 1 May 2021

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$1,421pp Total price $2,841
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$732pp Total price $1,464
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Simpson Kids

Whether you're travelling with babes in arms, toddlers or school-age children, our Simpson Kids programme will help you find the perfect holiday to suit your family. From hotels with expert childcare to villas with complimentary infant packs and garden games for the kids, we have everything you need for a stress-free family holiday.
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Acqua di Mare – Villa Bella

Lefkada, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Stunning beach front location
  • Stylish and contemporary
  • Lawned garden
  • Simpson family extras available

Prices are based on 2 sharing for 7 nights on Sunday 2 May 2021

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$1,434pp Total price $2,867
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The Harbour House

Paxos, Greece

Villa | Bedroom 1 | Sleeps 2

  • Delightful harbour house suite
  • Gaios waterfront
  • Roof terrace with harbour views
  • Shops and restaurants on your doorstep

Prices are based on 2 sharing for 7 nights on Wednesday 6 October 2021

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$1,468pp Total price $2,935
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Casa di Maura

Meganissi, Greece

Villa | Bedrooms 4 | Sleeps 6

  • Stylish contemporary house
  • On the edge of Spartachori village
  • Stunning sea views
  • Tavernas/mini-markets 2min walk

Prices are based on 2 sharing for 7 nights on Sunday 2 May 2021

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$1,478pp Total price $2,955
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Loutsa Villa

Ithaca, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Superbly positioned villa
  • Bright and airy
  • Direct beach access
  • Taverna and café 10min walk

Prices are based on 2 sharing for 7 nights on Saturday 1 May 2021

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$1,494pp Total price $2,987
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$806pp Total price $1,611
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Reviews

Simpson Travel in the press

  • ‘[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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Holiday ideas

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Travel advice from the Foreign Office

For up-to-date advice and information on travelling abroad, including passports, visas and health and safety, please visit the Foreign Commonwealth & Development Office website or call 020 7008 1500.

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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