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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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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 8 October 2022

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$779pp Total price $1,558
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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 9 October 2022

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  • Villa

Prices
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$801pp Total price $1,601
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Villa Maria

Corfu, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Simpson family extras available
  • Prime NE Corfu location
  • Pretty single-storey villa
  • Attractive garden

Prices are based on 2 sharing for 7 nights on Sunday 23 October 2022

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  • Villa

Prices
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$823pp Total price $1,645
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Simpson Secret – Crete

Rethymno & Central Crete, Crete, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Charming house in rural village
  • Set amongst rolling hills and vineyards
  • Carefully tended garden with barbecue and bread oven
  • Authentic Crete at its best

Prices are based on 2 sharing for 7 nights on Tuesday 31 May 2022

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  • Villa

Prices
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$823pp Total price $1,645
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Reserve now for 2023 with a fully refundable deposit of $650

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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 9 October 2022

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  • Villa

Prices
from

$840pp Total price $1,680
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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 18 October 2022

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  • Villa

Prices
from

$843pp Total price $1,685
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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 on Wednesday 5 October 2022

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  • Villa

Prices
from

$845pp Total price $1,689
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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 on Sunday 16 October 2022

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  • Villa

Prices
from

$853pp Total price $1,705
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Reserve now for 2023 with a fully refundable deposit of $650

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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 8 October 2022

Accommodation Only

  • Villa

Prices
from

$861pp Total price $1,722
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Reserve now for 2023 with a fully refundable deposit of $650

Use our Advanced Registration service to secure your 2023 holiday with a deposit of $650, fully refundable when prices are published

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Villa Alba

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 8 October 2022

Accommodation Only

  • Villa

Prices
from

$861pp Total price $1,722
View details
Reserve now for 2023 with a fully refundable deposit of $650

Use our Advanced Registration service to secure your 2023 holiday with a deposit of $650, fully refundable when prices are published

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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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Holiday ideas

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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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