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Luxury family holidays in Italy

Italy is a destination that welcomes guests of all ages with a warm embrace of wholesome food and wine, sun-kissed landscapes and a host of interesting places to explore. And at the end of the day, there’s always the chance to gather round the dining table to enjoy that precious time together.

For little ones who want room to run around, the sprawling Italian countryside never runs out of space for exploring, horseriding or cycling and our villas, with their extensive, lovingly tended gardens, private pools and stone terraces, only enhance the pleasures of the great outdoors.

Even history lessons take place outside here, with the historic spires, domes and towers of Florence, Siena, Pisa 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 warmly 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.

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Showing search results for 'Italy'. (28 results found)

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Tuscany, Italy

Accom only prices from £770 Help

Price is based on 1 week, accommodation only.

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Villa | 3 bedrooms | Sleeps 6

  • Comfortable refurbished villa
  • Set in an extensive manicured garden
  • Ideal for two families travelling together

Tuscany, Italy

Accom only prices from £800 Help

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Villa | 2 bedrooms | Sleeps 4

  • Delightful Tuscan villa
  • Beautiful countryside views
  • Comfortable interiors

Puglia, Italy

Accom only prices from £1,100 Help

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Villa | 2 bedrooms | Sleeps 5

  • Enchanting trulli house
  • Val d’Itria location
  • Flexible Accommodation

La Madonnina

United by warm welcomes, excellent service and attention to detail, our handpicked Simpson Hotels include our unique Adult Only Collection and, for families, comfortable, versatile accommodation in locations well suited to guests of all ages.
Simpson Hotels

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Tuscany, Italy

Prices from £608pp Help

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

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Hotel | 1-2 bedrooms | Sleeps 2-4

  • Delightfully small Simpson Hotel
  • Stunning views
  • Two 2-bedroom suites, one cottage

Tuscany, Italy

Accom only prices from £1,330 Help

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Villa | 5 bedrooms | Sleeps 10

  • Tranquil, spacious retreat
  • Stunning panoramic views
  • Comfortable interiors

Puglia, Italy

Accom only prices from £1,350 Help

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Villa | 2 bedrooms | Sleeps 4

  • Two-bedroom suite
  • Stunning sea views
  • Direct access to rocky beach

Tuscany, Italy

Accom only prices from £1,360 Help

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Villa | 3 bedrooms | Sleeps 6

  • Stylish and comfortable barn conversion
  • Extensive garden with small lake
  • Cooking classes available

Tuscany, Italy

Accom only prices from £1,990 Help

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Villa | 3 bedrooms | Sleeps 6

  • Beautifully restored farm house
  • Stunning panoramic views
  • Heated pool

Puglia, Italy

Accom only prices from £2,100 Help

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Villa | 4 bedrooms | Sleeps 8

  • Spacious luxury villa
  • Private gardens
  • 15-minute drive to Galipolli and beaches

Puglia, Italy

Accom only prices from £2,300 Help

Price is based on 1 week, accommodation only.

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Villa | 3 bedrooms | Sleeps 6

  • Beautifully restored trulli
  • Ideal for families or couples
  • Expansive lawned grounds