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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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Loggos View House

Paxos, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Delightful and charming villa
  • Beautiful sea views
  • Light and airy
  • Loggos 20min walk or 2min drive

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

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$1,619pp Total price $3,237
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Villa Selina

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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$1,627pp Total price $3,254
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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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Diamantina

Corfu, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Historic renovated cottage
  • Central village location (Agios Stephanos)
  • Delightful walled courtyard
  • Simpson family extras available

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

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$1,650pp Total price $3,299
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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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Kastanida House

Paxos, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Welcoming family home
  • Comfortable and private
  • Delightful extensive walled gardens
  • Loggos/Lakka/Gaios 10min drive

Prices are based on 2 sharing for 7 nights

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$1,665pp Total price $3,329
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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

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

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$1,665pp Total price $3,329
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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.
Simpson Kids

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Villa Georgia

Corfu, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Beautifully positioned villa
  • Stunning views
  • Stylish and elegant
  • Use of Bella Mare Hotel facilities

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

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$1,668pp Total price $3,336
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Spilia Bay House

Meganissi, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Stunning sea views
  • Modern interiors
  • Walking distance to Spilia Beach
  • Close to Spartochori and tavernas

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

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$1,668pp Total price $3,336
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Villa Simi

Lefkada, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Stylish east coast villa
  • Beautiful sea views
  • Stylish interiors
  • Short stroll to private pontoon

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

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$1,700pp Total price $3,400
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Villa Akoni

Meganissi, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Stylish contemporary villa
  • Finished to a high spec
  • Beautiful sea views
  • Waterside tavernas at Vathy 5min walk

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

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$1,702pp Total price $3,404
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Villa Mentes

Meganissi, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Stylish contemporary villa
  • Finished to a high spec
  • Beautiful sea views
  • Waterside tavernas at Vathy 5min walk

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

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  • Return flights from London Gatwick Airport
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$1,702pp Total price $3,404
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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

  • Holidays in Corsica
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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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