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  • Destinations

    Destinations

    France

    France

    • Provence
    • The Dordogne & South West
    • Vendée
    • Aquitaine Coast
    • Ile de Ré

    Mallorca

    Mallorca

    • Pollensa & Puerto Pollensa

    Greece

    Greece

    • Corfu
    • Crete
    • Ithaca
    • Kefalonia
    • Lefkada
    • Meganissi
    • Paxos
    • Zakynthos
    • Sivota & Epirus

    Turkey

    Turkey

    • Akyaka
    • Bozburun Peninsula
    • Islamlar & Uzumlu
    • Kalkan
    • Kaş

    Italy

    Italy

    • Tuscany
    • Umbria
    • Puglia

    Corsica

    Corsica

    • Calvi & The Balagne
    • Porto Vecchio & Bonifacio
    • The Valinco
  • Villas

    Villas

    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
    Family villas
  • Hotels

    Hotels

    Simpson Hotels
    Partner hotels
    Family hotels
    Beachfront hotels
    Adult-only hotels
    Romantic hotels for two
    Hotels with childcare
    Car-free hotels
  • Holiday inspiration

    Holiday inspiration

    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 Greece
    • Special Interest Holidays

    Family holidays

    Family holidays

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

    Collections

    Collections

    • Simpson Exclusive
    • Simpson Secrets
    • Simpson Hotels
    • Simply Simpson
    • Simpson Kids
    • Simpson Bespoke

    More inspiration

    More inspiration

    • Our Blog
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    About us

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Luxury Greek Island holidays

Picture the quintessential Greek holiday scene: small white pebble coves and soft sandy beaches; friendly harbourside tavernas and silvery olive groves; tiny hamlets, historic towns and peaceful churches. Our carefully chosen Greek Island destinations and handpicked collection of luxury villas and boutique hotels offer all this and more. 

Often described as stepping back in time, the Greek Islands offer a heady combination of ancient landscapes, stunning coastlines and picturesque fishing villages. And yet within this mix of fascinating history and rich culture, a Simpson Travel luxury villa or hotel holiday allows you to experience the Mediterranean at your own pace, which can be as slow as you want it to be.

Which Greek Island is for you?

While the blue seas, stunning views and pine-scented countryside are part of all our Greek Island destinations, there are distinguishing features that give each island its own identity.

Explore the UNESCO-listed Corfu Town or ancient ruins of Knossos in Crete; tap into the exclusive tranquillity of Meganissi or the simplicity of a beach holiday on diminutive Paxos – whichever you choose, there’s a unique Greek Island holiday waiting to happen. You may prefer Skopelos and Kefalonia as featured in the movies, or the Homeric history of Ithaca, but for a family holiday with young children, our crèches and children’s clubs on Lefkada and Zakynthos tick many boxes. After all, with professional nannies on standby, mummies and daddies can have some well-earned time out.

Things to do on the Greek Islands

When you want to venture further afield than your own private villa swimming pool or the peaceful garden of your boutique hotel, you’ll be spoiled for choice. Hire a boat and find a secluded bay far away from the modern world. Explore the winding streets of pretty villages or go walking through pine forests and ancient olive groves. A Greek Island holiday with Simpson Travel allows you to experience the authentic Mediterranean – and that includes the food: freshly caught fish, hearty meat dishes and shining Greek salads that can be consumed leisurely with a carafe of wine at a table overlooking the sea.

This is your Greek Island holiday – so what will it be?

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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 per person, based on 2 sharing for 7 nights
on Sunday 4 May 2025

Accommodation Only
Villa
Prices
from
£285pp
Total price £570
View details
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 per person, based on 2 sharing for 7 nights
on Sunday 5 October 2025

Accommodation Only
Villa
Prices
from
£335pp
Total price £670
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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Apothikes Beach Suites

Palekastro & Eastern 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 per person, based on 2 sharing for 7 nights
on Tuesday 29 April 2025

Accommodation Only
Villa
Prices
from
£360pp
Total price £720
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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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 per person, based on 2 sharing for 7 nights
on Sunday 4 May 2025

Accommodation Only
Villa
Prices
from
£360pp
Total price £720
View details
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Muses Beach Villas – Erato

Palekastro & Eastern Crete , Crete , Greece

Villa | Bedroom 1 | Sleeps 2

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

Prices are per person, based on 2 sharing for 7 nights
on Tuesday 21 October 2025

Accommodation Only
Villa
Prices
from
£368pp
Total price £735
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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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 per person, based on 2 sharing for 7 nights
on Sunday 4 May 2025

Accommodation Only
Villa
Prices
from
£390pp
Total price £780
View details
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Muses Beach Villas – Cleo

Palekastro & Eastern Crete , Crete , Greece

Villa | Bedroom 1 | Sleeps 2

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

Prices are per person, based on 2 sharing for 7 nights
on Tuesday 21 October 2025

Accommodation Only
Villa
Prices
from
£410pp
Total price £820
View details
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Villa Palekastro

Palekastro & Eastern 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 per person, based on 2 sharing for 7 nights
on Tuesday 29 April 2025

Accommodation Only
Villa
Prices
from
£410pp
Total price £820
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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Elia Beach Villa

Ithaca , Greece

Villa | Bedrooms 2 | Sleeps 4

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

Prices are per person, based on 2 sharing for 7 nights
on Sunday 4 May 2025

Accommodation Only
Villa
Prices
from
£410pp
Total price £820
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

Close
Go to property page

Lemonia Beach Villa

Ithaca , Greece

Villa | Bedrooms 2 | Sleeps 4

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

Prices are per person, based on 2 sharing for 7 nights
on Sunday 5 October 2025

Accommodation Only
Villa
Prices
from
£410pp
Total price £820
View details
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Why travel with us..?

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See what others say about us

See what others say about us
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

  • 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
  • Runner up Telegraph travel awards 2023

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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.

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