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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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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 2 May 2021

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Prices
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$983pp Total price $1,966
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Prices
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$404pp Total price $807
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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

Package holiday

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  • Departs 04 May 2021

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$1,022pp Total price $2,044
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  • Departs 19 Oct 2021

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Muses Beach Villas – Cleo

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

Package holiday

  • Villa
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  • Departs 04 May 2021

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$1,095pp Total price $2,189
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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 Saturday 1 May 2021

Package holiday

  • Villa
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Prices
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$1,138pp Total price $2,275
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  • Villa

Prices
from

$454pp Total price $907
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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 Saturday 1 May 2021

Package holiday

  • Villa
  • Return flights from London Gatwick Airport
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    Included option varies by selected accommodation, arrival airport & date

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Prices
from

$1,138pp Total price $2,275
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  • Villa

Prices
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$454pp Total price $907
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Villa Vereniki

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 4 May 2021

Package holiday

  • Villa
  • Return flights from London Gatwick Airport
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Prices
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$1,167pp Total price $2,334
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Muses Beach Villa – Thalia

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

Package holiday

  • Villa
  • Return flights from London Gatwick Airport
  • Car hire or transfers

    Included option varies by selected accommodation, arrival airport & date

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  • Departs 04 May 2021

Prices
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$1,167pp Total price $2,334
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  • Villa
  • Departs 19 Oct 2021

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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 20 April 2021

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Prices
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$1,178pp Total price $2,356
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  • Villa

Prices
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$633pp Total price $1,265
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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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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 Saturday 1 May 2021

Package holiday

  • Villa
  • Return flights from London Gatwick Airport
  • Car hire or transfers

    Included option varies by selected accommodation, arrival airport & date

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Prices
from

$1,207pp Total price $2,413
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Accommodation Only

  • Villa

Prices
from

$523pp Total price $1,045
View details
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 House

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 Saturday 1 May 2021

Package holiday

  • Villa
  • Return flights from London Gatwick Airport
  • Car hire or transfers

    Included option varies by selected accommodation, arrival airport & date

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Prices
from

$1,207pp Total price $2,413
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  • Villa

Prices
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$523pp Total price $1,045
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Simpson Travel in the press

  • ‘[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

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Travel advice from the Foreign Office

For up-to-date advice and information on travelling abroad, including passports, visas and health and safety, please visit the Foreign Commonwealth & Development Office website or call 020 7008 1500.

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.

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    Holiday Types

    • Couples holidays
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    Family Holidays

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