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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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Agni Cottage

Corfu, Greece

Villa | Bedroom 1 | Sleeps 2

  • Charming, romantic cottage
  • On Agni water's edge
  • Comfortable and cosy
  • Walking distance to tavernas

Prices are based on 2 sharing for 7 nights on Wednesday 19 October 2022

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  • Cottage

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$927pp Total price $1,854
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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 2 October 2022

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  • Villa

Prices
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$953pp Total price $1,905
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Reserve now for 2023 with a fully refundable deposit of $650

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Casa di Maura

Meganissi, Greece

Villa | Bedrooms 4 | Sleeps 6

  • Stylish contemporary house
  • On the edge of Spartachori village
  • Stunning sea views
  • Tavernas/mini-markets 2min walk

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

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$953pp Total price $1,906
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The Artist's House

Paxos, Greece

Villa | Bedroom 1 | Sleeps 2

  • Romantic stone house
  • Ideally positioned overlooking the sea
  • Bright and comfortable
  • Beach 5min walk

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

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$955pp Total price $1,909
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Villa Akoni

Meganissi, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Stylish contemporary villa
  • Finished to a high spec
  • Beautiful sea views
  • Waterside tavernas at Vathy 5min walk

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

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$959pp Total price $1,917
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Villa Oleana

Lefkada, Greece

Villa | Bedrooms 3 | Sleeps 6

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

Prices are based on 2 sharing for 7 nights on Sunday 9 October 2022

Accommodation Only

  • Villa

Prices
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$959pp Total price $1,918
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Reserve now for 2023 with a fully refundable deposit of $650

Use our Advanced Registration service to secure your 2023 holiday with a deposit of $650, fully refundable when prices are published

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The Stone House – Greece

Paxos, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Comfortable and charming house
  • Stunning 20m infinity pool
  • Delightful sea views
  • Spacious open-plan living area

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

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$985pp Total price $1,970
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Loggos View House

Paxos, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Delightful and charming villa
  • Beautiful sea views
  • Light and airy
  • Loggos 20min walk or 2min drive

Prices are based on 2 sharing for 7 nights on Sunday 2 October 2022

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$994pp Total price $1,987
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Moundela

Paxos, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Beautifully positioned new villa
  • Delightful sea views to Anti Paxos
  • Kafenion 10min walk
  • Beach/shops/restaurants 5min drive

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

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$1,011pp Total price $2,022
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Villa Flora

Paxos, Greece

Villa | Bedrooms 4 | Sleeps 8

  • Beautiful family villa
  • Splendid sea views
  • Spacious and shaded terraces
  • Beach 5min walk

Prices are based on 2 sharing for 7 nights on Sunday 2 October 2022

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  • Villa

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$1,050pp Total price $2,100
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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

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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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  • Destinations

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    • Provence
    • The Dordogne & South West
    • Vendée
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    Mallorca

    Mallorca

    • Fornalutx & Sóller
    • Pollença & Puerto Pollença

    Greece

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    • Corfu
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    • Villas with childcare
    • Luxury villas
    • Off the beaten track villas
    • Car-free villas
    • Large group villas
    • Villas together
    • Romantic villas for two
    • Family Favourite villas
    • Teen-friendly villas
    • Beachfront villas
    • Villas with heated pools
    • Villas near the beach
    • Villas near a restaurant

    Back

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    Back

  • Holiday inspiration

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    Holiday Types

    Holiday Types

    • Couples holidays
    • Beach holidays
    • Large group holidays
    • Car-free holidays
    • Twin Centre holidays
    • 10-night holidays
    • Countryside holidays
    • Honeymoons
    • Babymoons
    • Walking Holidays in Crete
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    Family Holidays

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    • Holidays with childcare
    • Easter holidays
    • Half-term holidays
    • Multi-gen holidays

    Collections

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    Our Blog

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