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Mallorca

  • Fornalutx & Sóller
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Greece

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

Turkey

  • Akyaka
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Italy

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Holiday inspiration

Holiday inspiration

Holiday Types

  • Couples holidays
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  • Car-free 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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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

Accommodation Only

  • Villa

Prices
from

$865pp Total price $1,729
View details
Reserve now for 2024 with a fully refundable deposit of $625

Use our Advanced Registration service to secure your 2024 holiday with a deposit of $625, fully refundable when prices are published

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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

Accommodation Only

  • Villa

Prices
from

$874pp Total price $1,747
View details
Reserve now for 2024 with a fully refundable deposit of $625

Use our Advanced Registration service to secure your 2024 holiday with a deposit of $625, fully refundable when prices are published

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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 10 October 2023

Accommodation Only

  • Villa

Prices
from

$875pp Total price $1,750
View details
Reserve now for 2024 with a fully refundable deposit of $625

Use our Advanced Registration service to secure your 2024 holiday with a deposit of $625, fully refundable when prices are published

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The Windmill

Paxos, Greece

Villa | Bedroom 1 | Sleeps 2

  • Intimate round house
  • Cosy and comfortable
  • Adults only
  • Stunning sea and island views

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

Accommodation Only

  • Villa

Prices
from

$885pp Total price $1,769
View details
Reserve now for 2024 with a fully refundable deposit of $625

Use our Advanced Registration service to secure your 2024 holiday with a deposit of $625, fully refundable when prices are published

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Kalami Bay House

Corfu, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Charming seafront property
  • Between Kalami and Kouloura
  • Small path down to the sea
  • Kalami tavernas/shops/beach 10min walk

Prices are based on 2 sharing for 7 nights on Sunday 22 October 2023

Accommodation Only

  • Villa

Prices
from

$885pp Total price $1,770
View details
Reserve now for 2024 with a fully refundable deposit of $625

Use our Advanced Registration service to secure your 2024 holiday with a deposit of $625, fully refundable when prices are published

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Loutsa Villa

Ithaca, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Superbly positioned villa
  • Bright and airy
  • Direct beach access
  • Taverna and café 10min walk

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

Accommodation Only

  • Villa

Prices
from

$894pp Total price $1,787
View details
Reserve now for 2024 with a fully refundable deposit of $625

Use our Advanced Registration service to secure your 2024 holiday with a deposit of $625, fully refundable when prices are published

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Kastanida House

Paxos, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Welcoming family home
  • Comfortable and private
  • Delightful extensive walled gardens
  • Loggos/Lakka/Gaios 10min drive

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

Accommodation Only

  • Villa

Prices
from

$904pp Total price $1,808
View details
Reserve now for 2024 with a fully refundable deposit of $625

Use our Advanced Registration service to secure your 2024 holiday with a deposit of $625, fully refundable when prices are published

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Steno

Paxos, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Delightfully comfortable house
  • Light and spacious
  • Wonderful sea views
  • Beach/Gaios 8min drive

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

Accommodation Only

  • Villa

Prices
from

$910pp Total price $1,819
View details
Reserve now for 2024 with a fully refundable deposit of $625

Use our Advanced Registration service to secure your 2024 holiday with a deposit of $625, fully refundable when prices are published

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Strati

Paxos, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Delightfully comfortable house
  • Light and spacious
  • Wonderful sea views
  • Beach/Gaios 8min drive

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

Accommodation Only

  • Villa

Prices
from

$910pp Total price $1,819
View details
Reserve now for 2024 with a fully refundable deposit of $625

Use our Advanced Registration service to secure your 2024 holiday with a deposit of $625, fully refundable when prices are published

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Villa Asteriskos

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 17 October 2023

Accommodation Only

  • Villa

Prices
from

$919pp Total price $1,837
View details
Reserve now for 2024 with a fully refundable deposit of $625

Use our Advanced Registration service to secure your 2024 holiday with a deposit of $625, fully refundable when prices are published

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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

  • Holidays in Corsica
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  • Villas in Turkey

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

Menu

  • Destinations

    Destinations

    France

    France

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

    Mallorca

    Mallorca

    • Fornalutx & Sóller
    • Pollença & Puerto Pollença

    Greece

    Greece

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

    Turkey

    Turkey

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

    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
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  • 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

    Collections

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    Our Blog

    Our Blog

    • Where to go
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    • What's new
    • Views and reviews
    • Family travel
    • 2023 holidays
    • Give the gift of travel
  • About us

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    Why Simpson Travel?
    Travel arrangements
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    Our heritage
    Awards
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