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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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Showing search results for 'Greece'. (161 results found)

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Blue Jasmine Hotel

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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Kefalonia, Greece

Prices from £727pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Hotel | 1-2 bedrooms | Sleeps 2-5

  • Stylish Simpson Hotel
  • Adult Only on select weeks
  • 12 air-conditioned suites

Lefkada, Greece

Prices from £781pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Villa | 1 bedroom | Sleeps 2

  • Romantic cottage just for two
  • Mesmerising sea views
  • Stylish interiors

Lefkada, Greece

Prices from £806pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Villa | 1 bedroom | Sleeps 2

  • Romantic cottage just for two
  • Mesmerising sea views
  • Stylish interiors

Palekastro & East Crete, Crete, Greece

Prices from £810pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Villa | 1 bedroom | Sleeps 2

  • Beachfront location
  • Authentic Crete
  • Short walk to tavernas

Mousses Crèche & Children's Club

From our Hatchlings Crèches that welcome little ones from the age of just 6 months to Tribe, a club created especially for teens, we’ve given our younger guests a place where they belong, with expert supervision and flexible session times to fit around your holiday.
Simpson Tots to Teens

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Lefkada, Greece

Prices from £813pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Villa | 2-3 bedrooms | Sleeps 2-6

  • 12 delightful 2-3 bedroom villas
  • First-class childcare with UK trained NNEB-qualified nannies
  • Large shared gated swimming pool

Lefkada, Greece

Prices from £819pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Villa | 1 bedroom | Sleeps 2

  • Romantic cottage just for two
  • Mesmerising sea views
  • Stylish interiors

Kefalonia, Greece

Prices from £820pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Apartment | 1 bedroom | Sleeps 2

  • Romantic open-plan suite
  • Beautiful sea views
  • Large roof terrace

Palekastro & East Crete, Crete, Greece

Prices from £835pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Villa | 1 bedroom | Sleeps 2

  • Beachfront location
  • Authentic Crete
  • Short walk to tavernas

Avithos Beach Estate

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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Kefalonia, Greece

Prices from £839pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Hotel | 2-4 bedrooms | Sleeps 2-6

  • Delightful Simpson Hotel
  • Close to one of Kefalonia's finest beaches
  • Six 2-bedroom and two 4-bedroom suites

Arosmari Village Hotel

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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Chania & West Crete, Crete, Greece

Prices from £854pp Help

Price is based on 2 sharing for 1 week, including flights, car hire or transfers.

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Hotel | 1-2 bedrooms | Sleeps 2-4

  • Simpson Hotel
  • Adult Only
  • A cluster of ten 1 and 2-bedroom cottages