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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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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 30 April 2023

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  • Villa

Prices
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$811pp Total price $1,622
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Reserve now for 2024 with a fully refundable deposit of $625

Use our Advanced Registration service to secure your 2024 holiday with a deposit of $625, fully refundable when prices are published

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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 – 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 2 May 2023

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  • Villa

Prices
from

$825pp Total price $1,650
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Reserve now for 2024 with a fully refundable deposit of $625

Use our Advanced Registration service to secure your 2024 holiday with a deposit of $625, fully refundable when prices are published

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Villa Isidora

Palekastro & Far East Crete, Crete, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Stunning contemporary villa
  • Mesmerising sea views
  • Gym
  • Close to vibrant Sitia

Prices are based on 2 sharing for 7 nights on Tuesday 24 October 2023

Accommodation Only

  • Villa

Prices
from

$827pp Total price $1,653
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Reserve now for 2024 with a fully refundable deposit of $625

Use our Advanced Registration service to secure your 2024 holiday with a deposit of $625, fully refundable when prices are published

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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.
Simpson Kids

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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 22 October 2023

Accommodation Only

  • Villa

Prices
from

$835pp Total price $1,670
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Reserve now for 2024 with a fully refundable deposit of $625

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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 4 October 2023

Accommodation Only

  • Villa

Prices
from

$837pp Total price $1,674
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Reserve now for 2024 with a fully refundable deposit of $625

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Myrtle Cottage

Paxos, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Delightful cottage with superb views
  • Recently renovated
  • Mature, flower-filled garden
  • Terrace for sun and shade

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

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  • Villa

Prices
from

$847pp Total price $1,694
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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 1 October 2023

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  • Villa

Prices
from

$862pp Total price $1,724
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Reserve now for 2024 with a fully refundable deposit of $625

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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 on Sunday 1 October 2023

Accommodation Only

  • Villa

Prices
from

$865pp Total price $1,729
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Reserve now for 2024 with a fully refundable deposit of $625

Use our Advanced Registration service to secure your 2024 holiday with a deposit of $625, fully refundable when prices are published

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Simply Simpson

The simple things in life often give the greatest pleasure and we believe our Simply Simpson Collection offers the chance to experience a more authentic taste of local living in some of the most idyllic locations in the Mediterranean. Take time to discover our comfortable, no-frills accommodation and join us on the road less travelled.
Simply Simpson

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Kouremenos Suites

Palekastro & Far East Crete, Crete, Greece

Apartment | Bedroom 1 | Sleeps 2-4

  • Simply Simpson suites
  • Magical east coast setting
  • Ideal for walkers
  • Short stroll to beach and tavernas

Prices are based on 2 sharing for 7 nights on Saturday 23 September 2023

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  • Suite

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$865pp Total price $1,730
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Villa Santolina

Lefkada, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Stylish contemporary villa
  • Beautiful views
  • Walking distance to sandy beach and tavernas
  • Simpson family extras

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

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  • Villa

Prices
from

$872pp Total price $1,743
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Reserve now for 2024 with a fully refundable deposit of $625

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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

  •  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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  • Villas in Greece
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  • Villas in Mallorca
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  • 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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