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  • 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

    Family holidays

    Family holidays

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

Paxos, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Beautifully appointed villa
  • Glorious sea views
  • Stylish and comfortable
  • Summer kitchen

Prices are based on 2 sharing for 7 nights on Sunday 19 May 2024

Package holiday

  • Villa
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Prices
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£2,133pp Total price £4,266
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The Yiameli Collection - Levandi

Zakynthos, Greece

Villa | Bedrooms 5 | Sleeps 9

  • Idyllic sea views
  • Beach 2-minute drive
  • Generous outdoor space
  • Tavernas 3-minute drive

Prices are based on 2 sharing for 7 nights on Sunday 19 May 2024

Package holiday

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  • Return flights from London Gatwick Airport
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Prices
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£2,171pp Total price £4,342
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Pelagia

Paxos, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Comfortable and charming house
  • Delightful sea views
  • Set in an acre of gardens
  • Gaios 10min drive

Prices are based on 2 sharing for 7 nights on Sunday 8 September 2024

Package holiday

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Prices
from

£2,344pp Total price £4,687
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  • Villa

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£1,647pp Total price £3,293
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Simpson Exclusive

The most luxurious of our villas include a dedicated pre-departure booking service to arrange all the indulgent essentials before you travel, from private chefs to spa treatments – and while you’re away, your personal Concierge will be on hand to add the finishing touches.
Simpson Exclusive

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Mikro Nisi House

Zakynthos, Greece

Villa | Bedrooms 5 | Sleeps 10

  • Beautiful Simpson Exclusive villa
  • Stunning waterfront location
  • Stylish and spacious interiors
  • Mesmerising sea views with sea access

Prices are based on 2 sharing for 7 nights on Sunday 5 May 2024

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Prices
from

£2,486pp Total price £4,972
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Simpson Exclusive

The most luxurious of our villas include a dedicated pre-departure booking service to arrange all the indulgent essentials before you travel, from private chefs to spa treatments – and while you’re away, your personal Concierge will be on hand to add the finishing touches.
Simpson Exclusive

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Villa Christianna

Corfu, Greece

Villa | Bedrooms 4 | Sleeps 8

  • Simpson Exclusive
  • Delightful spacious villa
  • Stylish and elegant
  • Magnificent sea views

Prices are based on 2 sharing for 7 nights on Sunday 6 October 2024

Package holiday

  • Villa
  • Return flights from London Gatwick Airport
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Prices
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£2,587pp Total price £5,174
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Villa Ammos

Chania & West Crete, Crete, Greece

Villa | Bedrooms 2 | Sleeps 2-4

  • Beachfront villa with infinity pool
  • Spectacular views across Kissamos Bay
  • Contemporary and stylish interiors
  • Walking distance to restaurants

Prices are based on 2 sharing for 7 nights

Package holiday

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  • Departs 27 Apr 2024

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£2,801pp Total price £5,602
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Villa Artemis

Corfu, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Stylish contemporary villa
  • Spacious interiors
  • Roof terrace with outstanding views
  • Infinity pool

Prices are based on 2 sharing for 7 nights on Sunday 8 September 2024

Package holiday

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Prices
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£2,911pp Total price £5,822
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The Village House

Ithaca, Greece

Villa | Bedrooms 5 | Sleeps 8

  • Beautifully renovated house
  • Characterful interiors
  • Gentle stroll to shops and tavernas
  • Perfect for large groups

Prices are based on 2 sharing for 7 nights

Package holiday

  • Villa
  • Return flights from London Gatwick Airport
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    Included option varies by selected accommodation, arrival airport & date

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  • Departs 11 Aug 2024

Prices
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£3,837pp Total price £7,673
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  • Departs 21 Jul 2024

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Simpson Exclusive

The most luxurious of our villas include a dedicated pre-departure booking service to arrange all the indulgent essentials before you travel, from private chefs to spa treatments – and while you’re away, your personal Concierge will be on hand to add the finishing touches.
Simpson Exclusive

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The Mantilari Estate

Rethymno & Central Crete, Crete, Greece

Villa | Bedrooms 11 | Sleeps 25

  • Simpson Exclusive
  • Luxury accommodation in 10-acre private estate
  • Two swimming pools (one heated)
  • Vineyard and wine cellar

Prices are based on 2 sharing for 7 nights on Saturday 18 May 2024

Accommodation Only

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Simpson Exclusive

The most luxurious of our villas include a dedicated pre-departure booking service to arrange all the indulgent essentials before you travel, from private chefs to spa treatments – and while you’re away, your personal Concierge will be on hand to add the finishing touches.
Simpson Exclusive

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Villa Klymene

Corfu, Greece

Villa | Bedrooms 5 | Sleeps 10

  • Simpson Exclusive
  • North east Corfu location
  • Spectacular sea views
  • Stylish and contemporary

Prices are based on 2 sharing for 7 nights

Package holiday

  • Villa
  • Return flights from London Gatwick Airport
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    Included option varies by selected accommodation, arrival airport & date

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  • Departs 29 Sep 2024

Prices
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£4,026pp Total price £8,052
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  • Departs 26 May 2024

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Why travel with us..?

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See what others say about us

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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

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  • Award - Telegraph 2018
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  • 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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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.

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