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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 Almyra

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 2 May 2023

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Prices
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$688pp Total price $1,375
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Reserve now for 2024 with a fully refundable deposit of $625

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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 2 May 2023

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  • Villa

Prices
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$689pp Total price $1,378
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Villa Asteriskos

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 April 2023

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Prices
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$702pp Total price $1,404
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Petrino House

Ithaca, Greece

Villa | Bedrooms 2 | Sleeps 2-4

  • Traditional stone house
  • Private pool with spectacular valley views
  • Beautiful gardens
  • Close to beaches and tavernas

Prices are based on 2 sharing for 7 nights on Sunday 8 October 2023

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Prices
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$704pp Total price $1,407
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Reserve now for 2024 with a fully refundable deposit of $625

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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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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 10 October 2023

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  • Villa

Prices
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$714pp Total price $1,428
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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 1 October 2023

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  • Villa

Prices
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$719pp Total price $1,437
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Amphitheatre Suites

Chania & West Crete, Crete, Greece

Villa | Bedrooms 1-2 | Sleeps 2-4

  • Five elegant and spacious suites
  • 1-bedroom suites (can be interconnected)
  • 2-bedroom suites with private pools
  • Communal pool

Prices are based on 2 sharing for 7 nights on Tuesday 25 April 2023

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  • Suite

Prices
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$722pp Total price $1,444
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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.
Simpson Secrets

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Simpson Secret – Epirus Coast

Sivota & Epirus, 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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Prices
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$736pp Total price $1,472
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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 15 October 2023

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$743pp Total price $1,485
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Villa Anthilia

Sivota & Epirus, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Stylish, contemporary interiors
  • Magnificent sea views
  • Single storey
  • Lawned garden

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

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$754pp Total price $1,507
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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

  •  Silver British travel awards 2017
  • Award - Telegraph 2018
  • Award - Baby 2019
  • Award - Conde Naste Traveller 2020
  • Award - Conde Naste Traveller 2021
  • Award - Conde Naste Traveller 2022
  •  Silver British travel awards 2021/22

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Holiday ideas

  • Holidays in Corsica
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  • Holidays in France
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  • Holidays in Greece
  • Villas in Greece
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  • Holidays in Mallorca
  • Villas in Mallorca
  • Holidays in Turkey
  • Villas in Turkey

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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    • Beachfront villas
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