Luxury family holidays in Italy

Italy is a destination that welcomes guests of all ages and family holidays come complete with the warm embrace of wholesome food and wine, sun-kissed landscapes and a host of interesting places to explore. And, as befits any exceptional gathering of family and friends, there’s always the chance to meet around the dining table of an evening to bring another day in the sunshine to a close.

For little ones who want room to run around, the sprawling Italian countryside never runs out of space for exploring, horse riding or cycling and our villas, with their extensive, lovingly tended gardens, private pools and stone terraces, only enhance the pleasures of the great outdoors. Or if your family holiday needs sea and sand, the beaches of Sicily and Liguria oblige with generosity – along with family-sized villas to bring everyone together.

In Tuscany, history lessons come to life with the historic spires, domes and towers of Florence, Siena and San Gimignano, the narrow winding streets of medieval hilltop villages or the mirror-like waterways of Venice – and when it comes to dining, parents can relax in the knowledge that children will be welcomed, whatever their age. From upmarket fine dining to pizza and a hundred different flavours of ice cream, there’s food in abundance for everyone, as well as some of the best wines in the world.

If you'd like a personal recommendation from our team of travel experts, just call 020 8392 5858 and find your Italian family holiday amore.


  • Villa Lidia, Umbria
    Please note that we now offer Sunday departures for stays at Villa Lidia. Perched on the top of a hill and set in lush five-hectare gardens, stillness and the rolling Umbrian countryside surround this characterful stone villa. The presence of...
    • Characterful and spacious villa
    • Set in glorious Umbrian countryside
    • Extensive gardens with stunning views
    • Comfortable and welcoming
    • 6 bedrooms (sleeps 12)
    • Guest...
    from £469pp
    based on 12 people
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  • Villa Donatella, Umbria
    Green and gold hillsides are laid out in every direction from this charming home. Surrounded by beautiful private gated grounds with a pool tucked into a small olive grove, the villa is immaculate inside and out, tastefully finished...
    • Calming and welcoming country house
    • Spacious and comfortable
    • Captivating views
    • Private swimming pool
    • 5 bedrooms (sleeps 9)
    • Complimentary wifi
    • Excellent location to explore...
    from £405pp
    based on 9 people
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  • Villa da Vinci, Tuscany
    This exceptional manor house can trace its history back to the 11th century, when it served as a watchtower overlooking the disputed territories between Florence and Siena. Almost a thousand years later there is still enormous value in this prime...
    • Exceptional manor house
    • Spacious and comfortable
    • Set in the heart of Chianti
    • Outstanding views
    • 7 air-conditioned bedrooms (sleeps 13)
    • Guest cottage
    • Complimentary...
    from £591pp
    based on 6 people
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  • Casetta Carina, Tuscany
    Surround yourself with all things Tuscan in this beautiful apartment within the 15th-century hamlet of Bricciano, near Barbischio. Occupying the east and south sides of an ancient stone house, bright and airy Casetta Carina is surrounded by...
    • Contemporary and comfortable apartment
    • Magnificent swimming pool
    • Ideally located to explore Chianti
    • 2 bedrooms (sleeps 2-3)
    • Complimentary wifi
    • Shops/restaurants/supermarket 10min...
    from £658pp
    based on 3 people
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  • Villa Passione, Tuscany
    In the beautiful Elsa Valley, this light-filled, three-bedroom barn conversion is a beautiful, whiter-than-white combination of function and form, complemented by the lush green of a sprawling lawned garden. Meticulously designed and styled by...
    • Stylish and comfortable barn conversion
    • Extensive garden with small lake
    • Cooking classes available
    • Private swimming pool
    • 3 bedrooms (sleeps 6)
    • Complimentary...
    from £533pp
    based on 6 people
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  • La Madonnina, Tuscany
    At the end of the drive leading up to this charming Simpson Hotel is the small 17th-century shrine to ‘The Little Mary’ who gave the house its name. As recently as the late 1980s, visitors came to make offerings there, but now, in this...
    • Delightfully small Simpson Hotel
    • Stunning views
    • Beautiful gardens
    • Shared swimming pool
    • 1 and 2 bedroom suites (sleeps 2-4)
    • Complimentary...
    from £488pp
    based on 4 people
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  • Casa al Colle, Tuscany
    Deep in the Garfagnana Mountains, Casa al Colle resides in one of the most soul stirring, authentically Italian parts of northern Tuscany. With its gorges, forests, rivers, medieval villages and churches, the region captured the hearts of the...
    • Tranquil, spacious retreat
    • Stunning panoramic views
    • Comfortable interiors
    • Private swimming pool 
    • 5 bedrooms (sleeps 10)
    • Complimentary wifi
    • Shops/restaurants 15min...
    from £445pp
    based on 10 people
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  • Casa Brilli, Tuscany
    A warm welcome at the end of a private road, the recently refurbished Casa Brilli is a comfortable choice near the Renaissance town of Castiglion Fiorentino. Beyond the expansive garden, perfect for little ones to let off steam, you have the...
    • Comfortable refurbished villa
    • Set in an extensive manicured garden
    • 2 separate levels for flexible families
    • Delightful outdoor pergola
    • 3 bedrooms (sleeps 2-6)
    • Large private swimming...
    from £474pp
    based on 6 people
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  • Villa Mille Desideri, Tuscany
    Surrounded by breathtaking Tuscan countryside, this six-bedroom villa invites gatherings of family and friends where relaxing and having fun together takes priority. It’s a magical place to stay, recently refurnished, but still full of its...
    • Beautifully positioned villa
    • Breathtaking views
    • Comfortable and welcoming
    • 5 double en-suite bedrooms
    • 1 single en-suite bedroom
    • Complimentary wifi
    • Swimming...
    from £862pp
    based on 11 people
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  • Villa Don Guido, Tuscany
    Villa Don Guido is a regal country house set in park-like grounds, expertly landscaped with precision-placed pines, firs, cypresses and hedges: in short, the archetypal Tuscan villa. The house itself is solid yet elegant; freshly painted yet with...
    • Regal country house
    • Traditional Italianate style
    • Extensive landscaped gardens
    • Private swimming pool
    • 6 bedrooms (sleeps 11)
    • Complimentary wifi
    • Tennis court and...
    from £616pp
    based on 11 people
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  • Villa Maddalena, Umbria
    In the northernmost corner of Lazio, but so close to Umbria (just 3.7km) that we couldn’t resist squeezing it in, the best of all worlds come together in this wonderful country villa. Half way between Florence and Rome, with an address like...
    • Wonderful country villa
    • Elegant and comfortable
    • Oustanding views
    • Lovely summer kitchen 
    • 5 bedrooms (sleeps 9)
    • Private swimming pool
    • Complimentary wifi
    • Walking...
    from £544pp
    based on 9 people
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  • Casa Angelica, Tuscany
    Panoramic green landscapes, traditional architecture and wine worth travelling for, of course we’re talking about Tuscany – and Casa Angelica offers you a taste of this 17th century beautifully converted apartment. You’ll find views like...
    • Beautiful converted apartment
    • 17th century building
    • 2 bedrooms (sleeps 2-4)
    • Private terrace with delightful views
    • Complimentary wifi
    • Ideal base for exploring Florence, Siena and San...
    from £481pp
    based on 4 people
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  • Villa Castrum, Tuscany
    Please note that the price listed is based on 10 people sharing. For larger parties, an additional two bedroom apartment (sleeps 4) is available as a supplement. This imposing villa stands on the hill-top site of the 1,000-year-old Castle of...
    • Magnificent country villa
    • In the heart of Chianti
    • Spacious and comfortable
    • Enchanting walled garden
    • 7 bedrooms (sleeps 14)
    • Complimentary wifi
    • Private swimming...
    from £685pp
    based on 10 people
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  • Return economy flights (flight supplements may be applicable depending on availability)
  • Government and local taxes, excluding visa charges
  • An air-conditioned car or return transfers, as specified in the property details
  • The assistance of our local representative overseas