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Luxury Villa Holiday in Siena

Self Drive to Tuscany, Italy

Best time to travel
May – Oct
Ideal length
7 nights
Sleeps up to
10 guests
From price based on full occupancy
€1,879 pp (incl flights)

At a glance

  • International return flights from Dublin to Pisa.
  • 7 days’ pre-arranged car rental in two Toyota Aygos, or similar.
  • 7 nights’ accommodation in a luxury villa in Siena.
  • Private gardens featuring an outdoor pool, a pool house with an outdoor kitchen and an alfresco dining area.
  • Explore the UNESCO World Heritage Site of historic Siena and enjoy incredible gastronomic experiences.
Let's plan your trip!
Villa Alfieri Pool
Villa Alfieri features a magnificent outdoor pool in the garden, accompanied by a pool house featuring an open kitchen.
Villa Alfieri Living Room
The traditional-style villa exhibits rustic charm with exposed stone walls, vaulted ceilings and antique furnishings.
Villa Alfieri Dining
Alfieri features an elegant sitting room and breakfast room, both with fireplaces, in addition to the spacious dining room and fully-equipped kitchen.
Villa Alfieri Bedroom
The villa's five well-appointed rooms all feature en-suite or private bathrooms.


Siena, a land of rolling hills and infinite culture, is a stunning destination for a private villa holiday. Sitting atop a Tuscan hill and overlooking the historic walled town, we’ve arranged a stay at a private villa that is the perfect base for poolside relaxation, hiking journeys, cultural exploration and gastronomic experiences. With two rental cars at your disposal, you can easily explore the region and enjoy trips to its charming medieval town. Siena’s historic centre is a trove of Italy’s rich history and culinary prowess. Enjoy days adventuring through the region’s stunning natural beauty and unwinding in your spacious garden and outdoor pool.

View all of our luxury holidays to Italy.

Trip Overview

Depart from Dublin to Pisa.

On arrival, pick up your pre-arranged rental cars and drive to your luxury villa in the Tuscan hills. Your home for the next seven nights, settle into your beautifully restored country house.

Make yourself at home.

While away days taking refreshing dips in your outdoor pool and lounging in the garden, admiring views down the Tuscan hills to the city of Siena below. The pergola in your garden is the perfect place for al fresco dining with your loved ones.

Aerial view of Villa Alfieri
Explore the walled city of Siena.

Siena is like an open-air museum of Medieval Italy, dense in monuments and art. Its historic centre, a listed UNESCO World Heritage Site, is famed for its cuisine, art, museums, medieval cityscape and the Palio, a legendary horse race through the city’s colourful streets.

Basilica of San Domenico, Siena
Enjoy incredible dining experiences.

A trip to Siena isn’t complete without a taste of its many gastronomic offerings. Siena’s eateries are diverse, from fine dining restaurants to jazz bars. Stop by local stores to pick up some regional specialities like coppa cured meat and pecorino cheese.

Stop by local stores to pick up some regional specialities like pecorino cheese
Hike through the stunning Tuscan countryside.

The sweeping views of Tuscany are the perfect setting for exciting hikes. Trek past verdant vineyards, up rolling hills and through aromatic olive groves. As you hike, pass through quaint villages and medieval towns.

Hike through the stunning Tuscan countryside
Drive to the international airport for your flight home.

Drop off your rental car and board your flight. 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 Alfieri

Villa Alfieri

Villa Alfieri is a beautifully restored country house in the heart of Italy. Ideally situated, it offers stunning panoramic views of the Tuscan hills and the medieval walled city of Siena.

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What people are saying

We loved the OROKO travel documents!  We are so impressed with the service we have received from your company. We will most certainly recommend you to our family and friends. You have thought of everything and we are very appreciative.

Sharon & Tom – Greece, September 2019


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