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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 Sunday 7 May 2023

Accommodation Only

  • Villa

Prices
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$755pp Total price $1,509
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Reserve now for 2024 with a fully refundable deposit of $625

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The Bay House

Ithaca, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Light and airy house
  • Beautiful views of Vathy
  • Comfortable and welcoming
  • Vathy shops and restaurants 5min drive

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

Accommodation Only

  • Villa

Prices
from

$765pp Total price $1,530
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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.
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Acqua di Mare – Villa Siena

Lefkada, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Stunning beach front location
  • Stylish and contemporary
  • Lawned garden

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

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  • Villa

Prices
from

$767pp Total price $1,534
View details
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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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 17 October 2023

Accommodation Only

  • Villa

Prices
from

$768pp Total price $1,535
View details
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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Reserve Now
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 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 8 October 2023

Accommodation Only

  • Villa

Prices
from

$782pp Total price $1,563
View details
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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The Saints

Corfu, Greece

Villa | Bedrooms 1-2 | Sleeps 2-4

  • A cluster of six 1 and 2-bedroom cottages
  • Each with private terrace
  • Stunning sea views
  • Shared swimming pool

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

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  • Cottage

Prices
from

$788pp Total price $1,575
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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 30 April 2023

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Prices
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$795pp Total price $1,589
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Villa Velanidia

Rethymno & Central Crete, Crete, Greece

Villa | Bedroom 1 | Sleeps 2

  • Attractive and idyllic stone house
  • A charming retreat for two
  • Delightful mature gardens
  • Unspoilt Crete at its best

Prices are based on 2 sharing for 7 nights on Tuesday 10 October 2023

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  • Villa

Prices
from

$801pp Total price $1,602
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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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The Harbour House

Paxos, Greece

Villa | Bedroom 1 | Sleeps 2

  • Delightful harbour house suite
  • Gaios waterfront
  • Roof terrace with harbour views
  • Shops and restaurants on your doorstep

Prices are based on 2 sharing for 7 nights on Wednesday 4 October 2023

Accommodation Only

  • Suite

Prices
from

$804pp Total price $1,608
View details
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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Kastanida House

Paxos, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Welcoming family home
  • Comfortable and private
  • Delightful extensive walled gardens
  • Loggos/Lakka/Gaios 10min drive

Prices are based on 2 sharing for 7 nights on Sunday 6 October 2024

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Prices
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$810pp Total price $1,619
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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
  • Villas in Corsica
  • Holidays in France
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  • Holidays in Greece
  • Villas in Greece
  • Holidays in Italy
  • Villas in Italy
  • 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
    • Villas with heated pools
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