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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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Showing search results for 'Greece'. (145 results found)

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Lefkada, Greece

Prices from £771pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Villa | 1 bedroom | Sleeps 2

  • Romantic cottage just for two
  • Mesmerising sea views
  • Stylish interiors

Lefkada, Greece

Prices from £796pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Villa | 1 bedroom | Sleeps 2

  • Romantic cottage just for two
  • Mesmerising sea views
  • Stylish interiors

Lefkada, Greece

Prices from £796pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

Close

Villa | 1 bedroom | Sleeps 2

  • Romantic cottage just for two
  • Mesmerising sea views
  • Stylish interiors

Palekastro & East Crete, Crete, Greece

Prices from £800pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Villa | 1 bedroom | Sleeps 2

  • Beachfront location
  • Authentic Crete
  • Short walk to tavernas

Mousses Crèche & Children's Club

You’ll find our two crèches and children’s clubs on the beautiful Greek islands of Lefkada and Zakynthos. They offer first-class childcare for tots to ten year olds, with qualified nannies and a flexible timetable so you can book session times to fit around your holiday.
Simpson Crèches

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Lefkada, Greece

Prices from £820pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Villa | 2-3 bedrooms | Sleeps 2-6

  • 12 delightful 2-3 bedroom villas
  • First-class childcare with UK trained NNEB-qualified nannies
  • Large shared gated swimming pool

Palekastro & East Crete, Crete, Greece

Prices from £825pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Villa | 1 bedroom | Sleeps 2

  • Beachfront location
  • Authentic Crete
  • Short walk to tavernas

Palekastro & East Crete, Crete, Greece

Prices from £850pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Villa | 1 bedroom | Sleeps 2

  • Beachfront location
  • Authentic Crete
  • Short walk to tavernas

Lefkada, Greece

Prices from £896pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

Close

Villa | 1 bedroom | Sleeps 2

  • Romantic cottage just for two
  • Mesmerising sea views
  • Stylish interiors

Rethymno & Central Crete, Crete, Greece

Prices from £922pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Villa | 1 bedroom | Sleeps 2

  • Delightful contemporary villa
  • Set in peaceful olive grove
  • Distant sea views

Rethymno & Central Crete, Crete, Greece

Prices from £922pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Villa | 3 bedrooms | Sleeps 6

  • Beautiful stone-built house
  • Rural location
  • Family friendly