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Luxury villas, boutique Simpson Hotels and unforgettable holidays

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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 Secrets

Our search for exceptional villas occasionally leads us along the road less travelled to find hidden gems just too lovely to leave behind. Aimed at the adventurous at heart, each Simpson Secret offers a unique take on what a holiday off the beaten track can be.
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Simpson Secret – Crete

Rethymno & Central Crete, Crete, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Charming house in rural village
  • Set amongst rolling hills and vineyards
  • Carefully tended garden with barbecue and bread oven
  • Authentic Crete at its best

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

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$825pp Total price $1,650
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Villa Isidora

Palekastro & Far East Crete, Crete, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Stunning contemporary villa
  • Mesmerising sea views
  • Gym
  • Close to vibrant Sitia

Prices are based on 2 sharing for 7 nights on Tuesday 24 October 2023

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  • Villa

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$827pp Total price $1,653
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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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Villa Maria

Corfu, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Simpson family extras available
  • Prime NE Corfu location
  • Pretty single-storey villa
  • Attractive garden

Prices are based on 2 sharing for 7 nights on Sunday 15 October 2023

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$835pp Total price $1,670
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Joanna's House

Paxos, Greece

Villa | Bedroom 1 | Sleeps 2

  • Delightful house for two
  • In traditional hamlet
  • Stunning sea views
  • Adults only

Prices are based on 2 sharing for 7 nights on Wednesday 4 October 2023

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$837pp Total price $1,674
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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 7 May 2023

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$847pp Total price $1,694
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Olive Cottage

Paxos, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Charming restored stone house
  • West coast with beautiful sunsets
  • Bright and airy
  • Lakka/tavernas/beach 5min drive

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

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$862pp Total price $1,724
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Thodoris House

Paxos, Greece

Villa | Bedrooms 2 | Sleeps 3

  • Delightfully restored house
  • In traditional hamlet
  • Light and comfortable
  • Adults only

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

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Prices
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$865pp Total price $1,729
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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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Kouremenos Suites

Palekastro & Far East Crete, Crete, Greece

Apartment | Bedroom 1 | Sleeps 2-4

  • Simply Simpson suites
  • Magical east coast setting
  • Ideal for walkers
  • Short stroll to beach and tavernas

Prices are based on 2 sharing for 7 nights on Saturday 23 September 2023

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$865pp Total price $1,730
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Villa Santolina

Lefkada, Greece

Villa | Bedrooms 3 | Sleeps 6

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

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

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$872pp Total price $1,743
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Spilia Bay House

Meganissi, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Stunning sea views
  • Modern interiors
  • Walking distance to Spilia Beach
  • Close to Spartochori and tavernas

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

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$874pp Total price $1,747
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Why travel with us..?

Talk to one of our experts

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CONTACT US

A brand you can trust

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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

  •  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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  • Destinations

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    France

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

    Mallorca

    Mallorca

    • Fornalutx & Sóller
    • Pollença & Puerto Pollença

    Greece

    Greece

    • Corfu
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    • Ithaca
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    • Meganissi
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    • Zakynthos
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    • Calvi & The Balagne
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  • 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

    Back

  • Hotels

    Hotels

    • Simpson Hotels
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    Back

  • 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 Crete
    • Special Interest Holidays
    • Experiences and Activities

    Family Holidays

    Family Holidays

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

    Collections

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    Our Blog

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