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Private Villa Holiday in Val d’Orcia

Self Drive to Tuscany, Italy

Best time to travel
May – Oct
Ideal length
7 nights
Sleeps up to
4 guests
From price based on full occupancy
€1,299 pp (incl flights)

At a glance

  • Direct return flights from Dublin to Pisa.
  • 7 days’ pre-arranged car rental in a Ford Grand C Max, or similar.
  • 7 nights’ accommodation in a luxury two bedroom villa in Val d’Orcia.
  • Private gardens featuring a spacious pool and alfresco dining area.
  • A wealth of opportunities to experience Val d’Orcia’s scenic hiking trails and picturesque towns and hamlets.
Let's plan your trip!
Jelanda Bedroom
Perfect for a small family or couple, the villa is a two bedroom, two bathroom property.
Jelanda Living Room
The villa features cosy interiors which are traditionally furnished.
Jelanda Patio
The villa has an outdoor dining space for al fresco candlelit dinners.
Spend afternoons on the outdoor terrace and by the garden pool.


Val d’Orcia’s beautiful landscape has inspired many Renaissance painters, enamoured by the castles, cypress trees and village hamlets that are dotted throughout the rolling hills. The ultimate destination for a secluded escape in Tuscany, we’ve created a suggested itinerary that features a luxury villa stay amid the olive groves and vineyards of the cultivated lands. With a rental car at your disposal, you can curate your very own experience, whether that’s driving to the ancient towns and cities of Tuscany, hiking the panoramic trails or simply unwinding with loved ones in your luxury Italian homestead.

View all of our luxury holidays to Italy.

Trip Overview

Depart from Dublin to Pisa.

On arrival, pick up your rental car and drive to your luxury villa in the rolling hills of Tuscany’s Val d’Orcia. Your home for the next seven nights, check out the spacious rooms and expansive outdoor space.

Relax in the postcard-perfect surroundings.

The private gardens are a wonderful space to relax the afternoon away. Lounge by the private pool and enjoy marvellous views over the surrounding countryside.

Pool at Villa Jalenda
Walk and hike along the trails of Val d’Orcia.

A landscape defined by rolling hills and vineyards, dotted with Renaissance villages and medieval ruins, this is undeniably one of the most scenic routes to experience in all of Italy. Explore at your leisure and stumble upon quaint spots to enjoy lunch.

Val d’Orcia Trails
Enjoy fabulous sunsets over Val d’Orcia.

Spend evenings socialising in the garden with family and friends. Watch the marvellous sunset over the Tuscan landscape before sitting down for a candlelit dinner alfresco. For extra special occasions, we can arrange a private chef.

Val d’Orcia Sunset
Dine out in Tuscany.

A region renowned for its marvellous cuisine, we would love to reserve tables at some of our favourite restaurants. We can also arrange tailored experiences like private wine tastings or visits to local cheesemakers and artisanal bakers.

Tuscan cuisine
Experience the picturesque towns that surround Val d’Orcia.

With a rental car at your disposal, set out to explore destinations like the Romanesque San Quirico d’Orcia and the fairytale town of Pienza, home to Flemish tapestries and 15th-century architecture.

Drive to the international airport for your flight home.

Drop off your rental car and board your flight home. Arrive in Dublin.

Tailoring your holiday

OROKO Itineraries are created with you in mind and no two are the same. These can be used to help plan your trip - or we can design a completely different itinerary to suit you.

Let's plan your trip!

Where to rest your head

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Villa Jelanda

The luxury villa of Jelanda lies along the rolling hills of the Tuscan countryside. One of the most romantic spots in the region, it is set within the cultivated lands of Val d’Orcia.

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What people are saying

In summary, it was a first class trip which we truly enjoyed. We have not one single complaint and in fact we tip our hats to OROKO, you exceeded our expectations. It is a great feeling when you just know everything is organised.

Rose & John – Sorrento, May 2019


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Your once in a lifetime experience starts here!