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France

  • Provence
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  • Vendée
  • Aquitaine Coast
  • Ile de Ré

Mallorca

  • Fornalutx & Sóller
  • Pollença & Puerto Pollença

Greece

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

Turkey

  • Akyaka
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  • Islamlar & Uzumlu
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Italy

  • Tuscany
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Corsica

  • Calvi & The Balagne
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Villas

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  • Family villas
Hotels

Hotels

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Holiday inspiration

Holiday inspiration

Holiday Types

  • Couples holidays
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  • Large group holidays
  • Car-free holidays
  • Twin Centre holidays
  • 10-night holidays
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  • Honeymoons
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  • Walking Holidays in Crete
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Family Holidays

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Luxury villa holidays in Greece

Once synonymous with family-run pensions and simple rooms to rent, Greece now offers some of the finest luxury villa holidays in the Mediterranean. The heart-felt hospitality, rich history and seemingly endless summers are still here, but today you’ll also find stunning contemporary accommodation with private pools, perfect for families and couples.

The Mediterranean holidays with more choice

With deep gorges and snow-capped peaks, pristine sandy beaches and gleaming white-pebble coves, the appeal of a villa holiday in Greece is as broad as the country’s astonishing history is long. From rural cottages to sleek seaside villas, the Simpson Travel luxury villa collection reflects this wonderful diversity, whilst incorporating the essentials of air-conditioning, wifi and a private pool in the vast majority of our properties.

Your guide to the Greek Islands

The larger islands such as Corfu, Crete, Lefkada, Zakynthos and Kefalonia offer the widest choice of villa holidays for families, couples or groups – and the most child-friendly beaches. On Zakynthos and Lefkada, you’ll find the renowned Simpson Travel Crèches & Children’s Clubs, whilst Sivota, Skopelos, Ithaca, Paxos, Kefalonia, Corfu and Crete offer a range of carefully chosen cottages and villas for two. For the slightly more adventurous, the smaller hideaways such as Paxos, Skopelos, Ithaca and Meganissi blend the charm of a classic Greek island escape with the luxury of a contemporary villa with its own private pool. And if island life is not your style, the pretty harbour town of Sivota gives you the chance to mix coast and the magnificent countryside of the interior.

So much choice can sometimes be a challenge, so if you’d like help narrowing down your personal selection, just get in touch with our Greece experts or explore our regional guides.

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Villa Porphyra

Lefkada, Greece

Villa | Bedrooms 4 | Sleeps 6

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

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

Accommodation Only

  • Villa

Prices
from

$722pp Total price $1,444
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 Almyra

Palekastro & Far East Crete, Crete, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Short walk to best beach in Crete
  • Set in unspoilt Xerokambos
  • Beautiful views
  • Short drive to tavernas

Prices are based on 2 sharing for 7 nights on Tuesday 10 October 2023

Accommodation Only

  • Villa

Prices
from

$722pp Total price $1,444
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 Kambos

Palekastro & Far East Crete, Crete, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Short walk to best beach in Crete
  • Set in unspoilt Xerokambos
  • Beautiful views
  • Short drive to tavernas

Prices are based on 2 sharing for 7 nights on Tuesday 17 October 2023

Accommodation Only

  • Villa

Prices
from

$722pp Total price $1,444
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 Fegari

The Gulf of Mirabello & South East Crete, Crete, Greece

Villa | Bedroom 1 | Sleeps 2-4

  • Delightful stone house 
  • Private swimming pool
  • Stunning sea views
  • Comfortable and welcoming

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

Accommodation Only

  • Villa

Prices
from

$722pp Total price $1,444
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 Rou Estate

Corfu, Greece

Villa | Bedrooms 2-5 | Sleeps 2-10

  • Beautifully restored hamlet
  • 14 stylish and elegant houses
  • Breathtaking views
  • Magnificent landscaped gardens

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

Accommodation Only

  • Villa

Prices
from

$743pp Total price $1,485
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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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The Bay House

Ithaca, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Light and airy house
  • Beautiful views of Vathy
  • Comfortable and welcoming
  • Vathy shops and restaurants 5min drive

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

Accommodation Only

  • Villa

Prices
from

$765pp Total price $1,530
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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Acqua di Mare – Villa Siena

Lefkada, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Stunning beach front location
  • Stylish and contemporary
  • Lawned garden

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

Accommodation Only

  • Villa

Prices
from

$767pp Total price $1,534
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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Muses Beach Villas – Urania

Palekastro & Far East Crete, Crete, Greece

Villa | Bedroom 1 | Sleeps 2

  • Stunning beachfront location
  • Authentic Crete
  • Short walk to tavernas
  • Close Palekastro

Prices are based on 2 sharing for 7 nights on Tuesday 17 October 2023

Accommodation Only

  • Villa

Prices
from

$768pp Total price $1,535
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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Neritos House

Ithaca, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Comfortable welcoming house
  • Stunning sea and mountain views
  • Light and airy
  • Vathy shops and restaurants 5min drive

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

Accommodation Only

  • Villa

Prices
from

$774pp Total price $1,548
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 Anlys

Lefkada, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Comfortable private villa
  • Superb sea and mountain views
  • Delightful pergola for dining
  • Simpson family extras available

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

Accommodation Only

  • Villa

Prices
from

$782pp Total price $1,563
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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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Why travel with us..?

Talk to one of our experts

Talk to one of our experts
CONTACT US

A brand you can trust

A brand you can trust

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
  • Villas in Corsica
  • Holidays in France
  • Villas in France
  • Holidays in Greece
  • Villas in Greece
  • Holidays in Italy
  • Villas in Italy
  • Holidays in Mallorca
  • Villas in Mallorca
  • Holidays in Turkey
  • 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
    • Kaş

    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
    Hotels with childcare
    Car-free hotels
  • 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

    • Simpson Exclusive
    • Simpson Secrets
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    • Simply Simpson
    • Simpson Kids
    • Simpson Bespoke

    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
    Advance Registration
    Our heritage
    Awards
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