Italy Villa Holidays

From the rolling hills and stately villas of Tuscany and Umbria to the sunshine playground of Puglia, villa holidays in Italy are unrivalled in their sheer variety, loved by couples, families and groups alike.

Villa holidays in Italy: Tuscany & Umbria

Cocooned by rolling hills and flanked by olive groves and vineyards, villas in Tuscany and Umbria offer a serene escape from the every day. It’s a region astonishingly rich in history, so you could find yourself not just immersed in one of the world’s most influential cultures, but staying in a former palazzo or grand villa dating back hundreds of years. Italian villa holidays bring you a unique blend of old and new, where traditional buildings have been enhanced with private swimming pools to give you a taste of luxury in a beautiful and authentic setting. And as the proportions of these venerable old buildings tended to be pretty palatial by modern standards, you’ll also enjoy plenty of room for your family holiday or group getaway.

By choosing a villa as your holiday base, you have complete freedom to set your own pace; whether that’s exploring medieval towns like Siena and San Gimignano or enjoying a wine tasting in Chianti, there's no shortage of memorable experiences. You can spend your days lounging by the pool, preparing meals with fresh local ingredients, or taking day trips to Florence, Pisa, or the picturesque Val d'Orcia. More than just a week in the sunshine, villa holidays in these delightful regions of Italy deliver charm, privacy, and a deep connection to the local heritage.

Italian villa holidays: Puglia

A villa holiday in Puglia brings you all the best of the country’s incredible cuisine and amazing history, plus fantastic beaches and long sunny days to enjoy them. It’s a region characterised by  whitewashed villages, ancient olive groves, and a stunning Adriatic coastline. Our holiday villas are nestled into quiet countryside close to charming towns like Ostuni, Lecce, Polignano and Locorotondo, making it easy to explore local markets, savour fresh seafood, and spend happy hours by the sea, enjoying the beach clubs which are such a part of the Puglia summer experience.

Your guide to villa holidays in Italy

From Renaissance cities to unique trulli houses, world-class vineyards to vibrant beach clubs, there’s so much to discover on an Italian villa holiday. Our portfolio is full of villas of all styles and sizes to suit, so to help you find the right holiday for you, take a look at our handy guides to Tuscany and Puglia, select your luxury villa and escape into a world of endless possibilities.

 


ITALY VILLAS BY DESTINATION


ITALY VILLAS BY HOLIDAY TYPE



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Quotes
  • We have just enjoyed one of the greatest holidays of our life. Trullo Ashi was absolute bliss - an incredible property, beautiful views, so clean, the pool was a dream, and the location was amazing - so many glorious places to visit nearby. Excellent service from Simpson too - we can't wait to return next year!!!

    Mr Thomas Worsley, Trullo Ashi, Puglia

  • "Casetta Carina near Gaiole in Chianti was a little piece of paradise… The pool has a stunning location and was a highlight of the holiday."

    Mr & Mrs P Livingstone, Casetta Carina, Tuscany

  • Our first time in Tuscany and how beautiful & amazingly unspoiled it is. La Madoninna, just remote enough, has stunning views across the lush beautifully maintained vineyards & olive groves, in abundance, across the valley. We were central to all the ancient hilltop towns, driving to Cortona, Montepulciano and Castiglion Fiorentino, and an easy & cheap (compared to UK), train ride to Florence and Arezzo. I think it's safe to say we will be returning.

    Mrs Karen Kidney, La Madoninna, Tuscany

  • Villa Flavia was perfect. Easy access for exploring yet really ideal for chilling out, especially the pool. Support from Francesco, Nico and his team was fantastic from the moment we booked and throughout our stay. Their attention to detail was exemplary. The icing on the cake, literally, was when Ketty visited the villa on Sunday morning to present me with a locally made cake to celebrate my birthday. Kindness like this is not forgotten. Once again many thanks for a truly enjoyable week.

    Lesley McHardy, Villa Flavia, Puglia