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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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Simpson Hotels

United by warm welcomes, excellent service and attention to detail, our handpicked Simpson Hotels include our unique Adult Only Collection and, for families, comfortable, versatile accommodation in locations well suited to guests of all ages.
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Katouna Suites

Lefkada, Greece

Hotel | Bedroom 1 | Sleeps 2

  • First Simpson Hotel on Lefkada
  • 10 stylish and contemporary suites
  • Adult Only
  • Mesmerising sea views

Prices are based on 2 sharing for 7 nights on Sunday 2 May 2021

Package holiday

  • Room & breakfast
  • 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

$961pp Total price $1,922
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Accommodation Only

  • Room & breakfast

Prices
from

$382pp Total price $763
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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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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

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

$983pp Total price $1,966
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Accommodation Only

  • Villa

Prices
from

$404pp Total price $807
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Simpson Hotels

United by warm welcomes, excellent service and attention to detail, our handpicked Simpson Hotels include our unique Adult Only Collection and, for families, comfortable, versatile accommodation in locations well suited to guests of all ages.
Simpson Hotels

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GK Beach Hotel

Chania & West Crete, Crete, Greece

Hotel | Bedrooms 1 | Sleeps 2-6

  • Delightfully situated Simpson Hotel
  • Beautiful gardens
  • 23 suites and a 2-bedroom penthouse, all with sea view
  • Beachfront bar and taverna

Prices are based on 2 sharing for 7 nights on Tuesday 19 October 2021

Package holiday

  • Room & breakfast
  • 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

$1,008pp Total price $2,015
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Accommodation Only

  • Room & breakfast

Prices
from

$337pp Total price $674
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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

  • 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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$1,022pp Total price $2,044
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  • Villa
  • 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
  • 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
from

$1,095pp Total price $2,189
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  • Departs 19 Oct 2021

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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
  • 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

$1,138pp Total price $2,275
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Accommodation Only

  • Villa

Prices
from

$454pp Total price $907
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 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

$1,138pp Total price $2,275
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Accommodation Only

  • Villa

Prices
from

$454pp Total price $907
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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The Waterside Apartments

Paxos, Greece

Apartment | Bedroom 1 | Sleeps 2

  • Two romantic waterside apartments
  • Charming village of Loggos
  • Comfortable interiors
  • Balconies overlooking the harbour

Prices are based on 2 sharing for 7 nights on Sunday 2 May 2021

Package holiday

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

    Included option varies by selected accommodation, arrival airport & date

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Prices
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$1,148pp Total price $2,295
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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
  • Car hire or transfers

    Included option varies by selected accommodation, arrival airport & date

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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

    Close
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  • Departs 04 May 2021

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

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Reviews

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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    Mallorca

    • Pollença & Puerto Pollença

    Greece

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    • Corfu
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    • Beachfront villas
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  • Hotels

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  • 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
    • Solo Travel
    • Experiences and Activities

    Family Holidays

    Family Holidays

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

    Collections

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    • Simpson Exclusive
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    Be Inspired

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