Beautiful Italian holiday rentals with swimming pool

Villa La Contessa Star

Villa La Contessa

Buonconvento, Siena Map

  • People 18
  • Beds 9
  • Showers 10

Villa La Contessa is a stunning villa near Siena, in the heart of the Val d'Orcia countryside in Chianti. Renovated in 2013, it has 9 bedrooms, 10 bathrooms, sauna, jacuzzi and outdoor pool.

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Casa San Lorenzo Star

Casa San Lorenzo

Dicomano, Mugello Map

  • People 4
  • Beds 2
  • Showers 1

Casa San Lorenzo is a delightful stone-built villa in Tuscany with 1 double bedroom and 1 twin bedroom and is part of an ancient farm complex that dates back to the late Middle Ages. Located on a hill in a splendid position that dominates the Mugello valley.

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Villa Rene' Star

Villa Rene'

Porto Cervo, Sardinia Map

  • People 10
  • Beds 6
  • Showers 6

Villa René is located in Liscia di Vacca, not far from the renowned Hotel Pitrizza and at few minutes driving from Porto Cervo center and offers an outstanding sea view. This stunning property with private pool can sleep up to 10 people in 5 bedrooms.

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Villa Pantogia Star

Villa Pantogia

Porto Cervo, Sardinia Map

  • People 12
  • Beds 6
  • Showers 6

Villa Pantogia is an asbolutely stunning property which enjoys an excellent location on the sea view hill of Pantogia, at just a short drive from the buzzing center of Porto Cervo and from the most glamorous beaches of the Costa Smeralda.

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Villa Lawrence Star

Villa Lawrence

Porto Cervo, Sardinia Map

  • People 14
  • Beds 7
  • Showers 6

Villa Lawrence is an elegant and highly exclusive villa located on a panoramic hill overlooking the “new marina” of Porto Cervo. This stunning Villa was designed for guests to enjoy it day and night and offers large open spaces and a glorious pool.

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Villa Gioiello Star

Villa Gioiello

Porto Cervo, Sardinia Map

  • People 8
  • Beds 3
  • Showers 2

Cosy and elegant, located in a quite area called Romazzino, near the most fabulous beaches of the Costa Smeralda and near the Pevero Golf Club, Villa Gioiello enjoys an incredible sea view and is ideal for a small family of a group of friends.

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Most popular properties


If your idea of a holiday is relaxing by the poolside, sunbathing, tanning, completely letting go to the stesses of daily life, all of which surrounded by a wonderful landscape, then Windows on Italy has the perfect solution for you. Our team has carefully selected a wonderful portfolio of the best handpicked villas and apartment holiday rentals with swimming pool throughout Italy to ensure you the most wonderful stay. Our properties range from beautifully restored cottages and farmhouses, rustic or modern countryside apatments to top deluxe villas all with magnificent private pools and terraced gardens providing utmost privacy for a truly relaxing holiday and total customer satisfaction.

What could be better than spending a day in a quiet oasis , surrounded by natural beauty, sipping a glass of wine by the pool, in a home equipped with every comfort. Choosing a property with Windows on Italy means being able to select spectacular pools, immersed in the most exclusive Italian locations : among the gentle Tuscan hills, on the shores of lakes, overlooking the bay of Amalfi, watching the sunset in Sardinia, or Sicily and much more. Contact our expert team to guide you in choosing the most suitable property to you!

What are you waiting for? Book your apartment or villa with swimming pool! Call us on +39 055 268510, write us an email or visit our offices in Florence.

Via dei Serragli 6 / R – Oltrarno area - San Frediano
Open Monday to Friday 9:00 to 13:00; 14:30 to 18:30