Filters

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.

+ Show more

Showing search results for 'Greece'. (142 results found)

Available

The Gulf of Mirabello & Southeast Crete, Crete, Greece

Prices from £660pp Help

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

Close

Villa | 1 bedroom | Sleeps 2-4

  • Five modern sea front suites
  • Magical setting in charming village
  • On Crete’s unspoilt southern shore

Meganissi, Greece

Prices from £686pp Help

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

Close

Villa | 3 bedrooms | Sleeps 6

  • Stylish contemporary villa
  • Finished to a high spec
  • Waterside tavernas at Vathy 5-minute walk

Lefkada, Greece

Prices from £793pp Help

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

Close

Villa | 1 bedroom | Sleeps 2

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

Lefkada, Greece

Prices from £819pp Help

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

Close

Villa | 1 bedroom | Sleeps 2

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

Lefkada, Greece

Prices from £819pp Help

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

Close

Villa | 1 bedroom | Sleeps 2

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

Palekastro & Far East Crete, Crete, Greece

Prices from £824pp Help

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

Close

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

Close

Lefkada, Greece

Prices from £839pp Help

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

Close

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

Palekastro & Far East Crete, Crete, Greece

Prices from £850pp Help

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

Close

Villa | 1 bedroom | Sleeps 2

  • Beachfront location
  • Authentic Crete
  • Short walk to tavernas

Kefalonia, Greece

Prices from £872pp Help

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

Close

Villa | 1 bedroom | Sleeps 2

  • Romantic suite with large terrace
  • Beautiful sea views
  • Gentle stroll to the sea

The Gulf of Mirabello & Southeast Crete, Crete, Greece

Prices from £877pp Help

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

Close

Villa | 1 bedroom | Sleeps 2-4

  • Four comfortable self-catering suites
  • Magical beachfront location
  • On Crete's unspoilt southern shore