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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

Prices are based on 2 sharing for 7 nights on Tuesday 4 April 2023

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$624pp Total price $1,248
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The Rou Estate

Corfu, Greece

Villa | Bedrooms 2-5 | Sleeps 2-10

  • Beautifully restored hamlet
  • 14 stylish and elegant houses
  • Breathtaking views
  • Magnificent landscaped gardens

Prices are based on 2 sharing for 7 nights on Sunday 16 October 2022

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$680pp Total price $1,359
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Sivota Senses – Villa Amalia

Sivota, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Innovative contemporary villa
  • Light and spacious
  • Sandy beach 5min walk
  • Sivota harbour 10min walk

Prices are based on 2 sharing for 7 nights on Sunday 30 April 2023

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$686pp Total price $1,372
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Sivota Senses – Villa Loukas

Sivota, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Innovative contemporary villa
  • Light and spacious
  • Sandy beach 5min walk
  • Sivota harbour 10min walk

Prices are based on 2 sharing for 7 nights on Sunday 30 April 2023

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$686pp Total price $1,372
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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 7 May 2023

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$688pp Total price $1,375
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Villa Palekastro

Palekastro & Far East Crete, Crete, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Short walk to Kouremenos Beach
  • Beautiful views
  • Gentle stroll to nearest taverna
  • Authentic Crete at its best

Prices are based on 2 sharing for 7 nights on Tuesday 17 October 2023

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$717pp Total price $1,433
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Villa Kambos

Palekastro & Far East Crete, Crete, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Short walk to best beach in Crete
  • Set in unspoilt Xerokambos
  • Beautiful views
  • Short drive to tavernas

Prices are based on 2 sharing for 7 nights on Tuesday 25 October 2022

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Prices
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$725pp Total price $1,450
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Reserve now for 2023 with a fully refundable deposit of $650

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Villa Anlys

Lefkada, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Comfortable private villa
  • Superb sea and mountain views
  • Delightful pergola for dining
  • Simpson family extras available

Prices are based on 2 sharing for 7 nights on Sunday 9 October 2022

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  • Villa

Prices
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$725pp Total price $1,450
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Reserve now for 2023 with a fully refundable deposit of $650

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Muses Beach Villas – Urania

Palekastro & Far East Crete, Crete, Greece

Villa | Bedroom 1 | Sleeps 2

  • Stunning beachfront location
  • Authentic Crete
  • Short walk to tavernas
  • Close Palekastro

Prices are based on 2 sharing for 7 nights on Tuesday 18 October 2022

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$736pp Total price $1,472
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Simpson Secret – Epiros Coast

Sivota, Greece

Villa | Bedroom 1 | Sleeps 2

  • Stylish and comfortable villa
  • Light and airy
  • Sandy and pebble beach at 30 paces
  • Taverna/shops 5min drive

Prices are based on 2 sharing for 7 nights on Sunday 30 April 2023

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$740pp Total price $1,479
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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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    Mallorca

    • Fornalutx & Sóller
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    • Romantic villas for two
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    • Teen-friendly villas
    • Beachfront villas
    • Villas with heated pools
    • Villas near the beach
    • Villas near a restaurant

    Back

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    • Honeymoons
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