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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 Exclusive

When only the best will do...


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Mimosa

Meganissi, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Simpson Exclusive
  • Stylish contemporary villa
  • Stunning sea views
  • Steps down to water's edge

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

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$1,158pp Total price $2,316
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Reserve now for 2023 with a fully refundable deposit of $650

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Villa Porphyra

Lefkada, Greece

Villa | Bedrooms 4 | Sleeps 6

  • Stylish contemporary villa
  • Beautiful views
  • Simpson family extras
  • Walking distance to sandy beach and 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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$1,180pp Total price $2,360
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The Kissamos Estate

Chania & West Crete, Crete, Greece

Villa | Bedrooms 1-3 | Sleeps 2-6

  • Eight luxury private villas with infinity pools
  • One, two or three bedrooms
  • Contemporary and stylish interiors
  • Heated pools available

Prices are based on 2 sharing for 7 nights on Saturday 29 April 2023

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$1,180pp Total price $2,360
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Thanelli

Paxos, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Superbly positioned villa
  • Outstanding sea views
  • Stylish and comfortable
  • Beach/tavernas 5min walk

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

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$1,182pp Total price $2,363
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Villa Heleni

Paxos, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Beautiful contemporary villa
  • Magnificent sea views
  • Spacious outside dining
  • Beach tavernas 5min walk

Prices are based on 2 sharing for 7 nights on Sunday 1 October 2023

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$1,182pp Total price $2,363
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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 9 October 2022

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$1,228pp Total price $2,456
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The Yiameli Collection - Meli

Zakynthos, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Sought-after NE Zakynthos coast location
  • Idyllic sea views
  • Elegant interiors
  • Beach 2-minute drive

Prices are based on 2 sharing for 7 nights on Sunday 25 September 2022

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$1,245pp Total price $2,490
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Kouloura Harbour View

Corfu, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Wonderfully positioned villa overlooking Kouloura Bay
  • Stunning sea views
  • Bright and spacious
  • Beach/taverna 5min drive

Prices are based on 2 sharing for 7 nights on Sunday 7 May 2023

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$1,277pp Total price $2,554
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Juniper House

Paxos, Greece

Villa | Bedrooms 3 | Sleeps 7

  • Comfortable and charming house
  • Stunning sea views
  • Beautiful gardens
  • 3 en-suite bedrooms

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

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  • Villa

Prices
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$1,278pp Total price $2,555
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Reserve now for 2023 with a fully refundable deposit of $650

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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 6 September 2022

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  • Villa

Prices
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$1,309pp Total price $2,617
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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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Why travel with us..?

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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

Awards

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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.

Copyright © 2022 Simpson Travel

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    • Villas with childcare
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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
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