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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 Sonatina

Rethymno & Central Crete, Crete, Greece

Villa | Bedroom 1 | Sleeps 2

  • Delightful contemporary villa
  • Set in peaceful olive grove
  • Wonderfully unspoilt
  • Distant sea views

Prices are based on 2 sharing for 7 nights on Tuesday 16 May 2023

Accommodation Only

  • Villa

Prices
from

$300pp Total price $600
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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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Kyparissi

Ithaca, Greece

Villa | Bedrooms 1-2 | Sleeps 2-4

  • Five charming suites
  • Wonderful position overlooking Kioni
  • Private terraces and balconies
  • Sea views

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

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  • Villa

Prices
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$379pp Total price $757
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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, school-age children or teens, 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 Family Holidays

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Mousses Crèche and Kids' Clubs

Lefkada, Greece

Villa | Bedrooms 2-3 | Sleeps 2-6

  • 12 delightful 2-3 bedroom villas
  • First-class childcare with fully qualified nannies
  • Large gated swimming pool
  • Spacious and secure lawned gardens

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

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  • Villa

Prices
from

$414pp Total price $827
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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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Arethusa Cottage

Ithaca, Greece

Villa | Bedroom 1 | Sleeps 2

  • Simply Simpson
  • Romantic open-plan cottage
  • Private pool and garden
  • 5min drive to Vathy

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

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  • Villa

Prices
from

$472pp Total price $944
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Reserve now for 2024 with a fully refundable deposit of $625

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Muses Beach Villas – Erato

Palekastro & Far East Crete, Crete, Greece

Villa | Bedroom 1 | Sleeps 2

  • Beachfront location
  • Authentic Crete
  • Short walk to tavernas
  • Close to Palekastro

Prices are based on 2 sharing for 7 nights on Tuesday 17 October 2023

Accommodation Only

  • Villa

Prices
from

$481pp Total price $962
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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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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Amalthia Cottage

Ithaca, Greece

Villa | Bedroom 1 | Sleeps 2

  • Simply Simpson
  • Romantic open-plan cottage
  • Private pool and garden
  • 5min drive to Vathy

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

Accommodation Only

  • Villa

Prices
from

$494pp Total price $988
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
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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Apothikes Beach Suites

The Gulf of Mirabello & South East Crete, Crete, Greece

Villa | Bedroom 1 | Sleeps 2-4

  • Magical beachfront location
  • On Crete's unspoilt southern shore
  • Four comfortable self-catering suites
  • Nearest taverna 1min walk

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

Accommodation Only

  • Suite

Prices
from

$516pp Total price $1,032
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
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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Rhodia Beach Villa

Ithaca, Greece

Villa | Bedroom 1 | Sleeps 2

  • Simply Simpson
  • Beautiful views to Kefalonia
  • West facing terrace
  • Private path 2-minute stroll to the beach

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

Accommodation Only

  • Villa

Prices
from

$527pp Total price $1,054
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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 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 2 May 2023

Accommodation Only

  • Villa

Prices
from

$535pp Total price $1,069
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

Close
Reserve Now
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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Nitsa’s House

Ithaca, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Simply Simpson
  • Traditional Ithacan house
  • Spectacular views
  • 3-minute walk to beach

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

Accommodation Only

  • Villa

Prices
from

$560pp Total price $1,119
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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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

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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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