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Family Friendly Villas in Sicily, Puglia, Tuscany & Formentera

Massimo Villas is not just another villa listing website where villa owners list their villas then manage their reservations. The beautiful holiday villas featured on this website are handled by Massimo’s team in Sicily and have been carefully selected for their location, style, facilities and welcome. Some villas are luxurious, and others are more simply furnished. Massimo visits many villas in Sicily, Puglia, Tuscany and Formentera and cherry picks the villas he knows his guests will love and makes sure they are adequately managed, saving you time and ensuring that you have a lovely villa holiday.

  • Beach Front Villas
  • Family Friendly Villas
  • Expert guidance to the best local beaches, nature reserves and historic sites for each and every villa in our collection
  • Save up to 50% when you make a last minute booking under 28 days before your stay.
  • Get a 10% discount when making a booking for your 2021 holiday

Some examples from the Massimo Villa Collection

An outstanding designer villa by the Vendicari Nature Reserve and beaches. 

Villa Secret Garden makes a stylish and secluded base for a big group of up to 16. 

Top features include an inviting 17-metre private pool, a rooftop terrace, outdoor kitchen and panoramic views to the sea over vineyards.

Villa Secret Garden

Sleeps 12 | €6300 - €10550 / week

  • Beautiful gardens and courtyard
  • Historic towns nearby
  • Designer villa

6 Rooms

6 Bathrooms




Looking out to valley views, Trullo Santa Pazienza has been beautifully restored to form a luxury villa.

Perfect for a family with magnificent easterly views, this retreat is an easy drive from a selection of sandy beaches and excellent restaurants. This villa well equipped and welcoming, with inviting areas for outdoor living and views out over the countryside.

Villa Trullo Santa Pazienza

Sleeps 9 | €3650 - €5600 / week

  • Beautiful gardens and courtyard
  • Remote place with stunning views
  • Enchanting trulli house

4 Rooms

4 Bathrooms




Built in the tradition of an old Tuscan farmhouse but with all the benefits of modern conveniences. Attention has been lavished on the interiors to give them an elegant feel while also maintaining the feeling of a family home. This property has been photographed several times and published in House & Garden, Elle Decor and the best selling book Private Tuscany. Personal touches are evident everywhere and combine to make it an excellent venue from which to explore the Tuscan and Umbrian countryside.

Villa Flavia

Sleeps 13 | € 4950 - € 11500 / week

  • Beautiful gardens and courtyard
  • Swimming pool
  • Spacious, modern interiors

7 Rooms

6 Bathrooms







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