Beautiful Italian holiday rentals with swimming pool

Villa San Marzano Star

Villa San Marzano

San Marzano Oliveto, Asti Map

  • People 11
  • Beds 5
  • Showers 7

Wonderful luxury villa with home-cinema room, a pool table and a floodlit tennis court, located in San Marzano Oliveto, in the heart of the Monferrato area, recently declared Unesco World Heritage. Surrounded by vineyards and a flowered garden, the property boasts a large spa and fitness area with sauna, Turkish bath, gym and indoor swimming pool. The property can accommodate up to 10+1 people, has 5 bedrooms and 7 bathrooms.

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Villa Zilio Star

Villa Zilio

Canelli, Asti Map

  • People 12
  • Beds 4
  • Showers 3

Stunning villa with swimming pool and external shower, located in the municipality of Canelli (Monferrato area), recently declared Unesco World Heritage. Surrounded by a lovely private garden with lawn and outdoor furniture, the villa can accommodate up to 8+4 people, has 4 bedrooms and 3 bathrooms.

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Villa il Poggio Star

Villa il Poggio

Punta Ala, Grosseto Map

  • People 13
  • Beds 7
  • Showers 6

Wonderful villa with panoramic terrace and dependance, located in Punta Ala, near Castiglione della Pescaia and only 2 km from the sea. It boasts a lovely garden with lawn, wood burning-oven and swimming pool. It can sleep up to 13 people, has 7 bedrooms and 6 bathrooms.

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Villa Infinito Star

Villa Infinito

Contrada Pizzillo, Ragusa Map

  • People 8
  • Beds 4
  • Showers 5

Superb villa with infinity pool and tennis/mini-soccer court, located in Contrada Pizzillo, just 12 km from Ragusa. Surrounded by a private garden with dining table and barbecue, it sleeps up to 8+1 people, has 4 bedrooms and 5 bathrooms.

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Villa Severino 47 Star

Villa Severino 47

Marche, San Severino Marche Map

  • People 47
  • Beds 16
  • Showers 18

Stunning rural complex comprising 3 properties (Villa Severino 27, Villa Severino Rustico e Villa Severino Dependance), situated in San Severino Marche, with magnificent views of the surrounding hills. It boasts a swimming pool, gym, private park, large equipped porch and an old deconsecrated church. It can accommodate up to 33+14 people, it has 16 bedrooms and 18 bathrooms.

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Villa Severino Dependance Star

Villa Severino Dependance

Marche, San Severino Marche Map

  • People 10
  • Beds 3
  • Showers 4

Charming villa with shared swimming pool and gym, located in San Severino Marche. It boasts a private garden and magnificent view of the surrounding hills. It can accommodate up to 6+4 people, has 3 bedrooms and 4 bathrooms.

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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
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