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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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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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Sapphire

Sivota, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Stylish and comfortable villa
  • Stunning sea views
  • Spacious pool terrace
  • Glorious sunsets

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

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$1,507pp Total price $3,013
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The Scented Garden

Paxos, Greece

Villa | Bedroom 1 | Sleeps 2

  • Stylish contemporary house
  • Light and spacious
  • Delightful walled garden
  • Adults only

Prices are based on 2 sharing for 7 nights

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$1,511pp Total price $3,022
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The Secret Garden

Paxos, Greece

Villa | Bedroom 1 | Sleeps 2

  • Stylish contemporary house
  • Light and spacious
  • Delightful walled garden
  • Adults only

Prices are based on 2 sharing for 7 nights

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  • Departs 02 May 2021

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$1,511pp Total price $3,022
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The Herb Garden

Paxos, Greece

Villa | Bedroom 1 | Sleeps 2

  • Stylish contemporary house
  • Light and spacious
  • Delightful walled garden
  • Adults only

Prices are based on 2 sharing for 7 nights

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  • Departs 02 May 2021

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$1,511pp Total price $3,022
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Olive Cottage

Paxos, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Charming restored stone house
  • West coast with beautiful sunsets
  • Bright and airy
  • Lakka/tavernas/beach 5min drive

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

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$1,519pp Total price $3,037
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Simpson Secrets

Our search for exceptional villas occasionally leads us along the road less travelled to find hidden gems just too lovely to leave behind. Aimed at the adventurous at heart, each Simpson Secret offers a unique take on what a holiday off the beaten track can be.
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Simpson Secret – Corfu

Corfu, Greece

Villa | Bedroom 1 | Sleeps 2

  • Stylish and secluded
  • Private pool and Jacuzzi
  • Stunning sea views
  • Restaurants, shops and beaches 5min drive

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

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$1,544pp Total price $3,088
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Kalami Bay House

Corfu, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Charming seafront property
  • Between Kalami and Kouloura
  • Small path down to the sea
  • Kalami tavernas/shops/beach 10min walk

Prices are based on 2 sharing for 7 nights

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  • Departs 02 May 2021

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$1,572pp Total price $3,144
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Joanna's House

Paxos, Greece

Villa | Bedroom 1 | Sleeps 2

  • Delightful house for two
  • In traditional hamlet
  • Stunning sea views
  • Adults only

Prices are based on 2 sharing for 7 nights

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  • Departs 02 May 2021

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$1,606pp Total price $3,212
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Thodoris House

Paxos, Greece

Villa | Bedrooms 2 | Sleeps 3

  • Delightfully restored house
  • In traditional hamlet
  • Light and comfortable
  • Adults only

Prices are based on 2 sharing for 7 nights

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  • Departs 02 May 2021

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$1,613pp Total price $3,226
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The Windmill

Paxos, Greece

Villa | Bedroom 1 | Sleeps 2

  • Intimate round house
  • Cosy and comfortable
  • Adults only
  • Stunning sea and island views

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

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  • Villa
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$1,613pp Total price $3,226
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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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