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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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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

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

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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 Sunday 7 May 2023

Accommodation Only

  • Villa

Prices
from

$937pp Total price $1,874
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Reserve now for 2024 with a fully refundable deposit of $625

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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

Accommodation Only

  • Villa

Prices
from

$942pp Total price $1,883
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Reserve now for 2024 with a fully refundable deposit of $625

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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 on Tuesday 23 May 2023

Accommodation Only

  • Villa

Prices
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$948pp Total price $1,895
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Reserve now for 2024 with a fully refundable deposit of $625

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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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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 11 October 2023

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  • Cottage

Prices
from

$960pp Total price $1,920
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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 14 May 2023

Accommodation Only

  • Villa

Prices
from

$972pp Total price $1,944
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Reserve now for 2024 with a fully refundable deposit of $625

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Villa Heleni

Paxos, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Beautiful contemporary villa
  • Magnificent sea views
  • Spacious outside dining
  • Beach tavernas 5min walk

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

Accommodation Only

  • Villa

Prices
from

$972pp Total price $1,944
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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 View

Meganissi, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Stunning sea views
  • Spacious modern interiors
  • Beautiful roof terrace
  • Walking distance to Spilia Beach

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

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  • Villa

Prices
from

$975pp Total price $1,950
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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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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

Accommodation Only

  • Villa

Prices
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$997pp Total price $1,994
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Juniper House

Paxos, Greece

Villa | Bedrooms 3 | Sleeps 7

  • Comfortable and charming house
  • Stunning sea views
  • Beautiful gardens
  • 3 en-suite bedrooms

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

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  • Villa

Prices
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$1,004pp Total price $2,007
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Why travel with us..?

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A brand you can trust

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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

  •  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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    • Romantic villas for two
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