Beautiful Italian holiday rentals with swimming pool

Villa Rekhale Star

Villa Rekhale

Rekhale, Pantelleria Map

  • People 8
  • Beds 4
  • Showers 4

Typical Sicilian building with swimming pool, carefully restored, located on the island of Pantelleria. Surrounded by a large Mediterranean park with outdoor lounge/dining area, the property can accommodate up to 8 people, it has 4 bedrooms and 4 bathrooms.

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Villa Morello Star

Villa Morello

Barberino Val d'Elsa area, San Gimignano Map

  • People 37
  • Beds 14
  • Showers 14

Stunning luxury estate with pool and spa area, situated in the Chianti countryside between Siena and Florence. The property consists of 4 typical Tuscan buildings with exposed stone walls, surrounded by a large private garden. It can accommodate up to 37 people, has 14 bedrooms and 14 full bathrooms.

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Villa la Goccia Star

Villa la Goccia

Porto Rotondo, Sardinia Map

  • People 16
  • Beds 8
  • Showers 13

Marvellous villa nestled in an enchanting location with breathtaking views of Porto Rotondo Gulf. A house set in the lush greenery of Costa Smeralda with direct sea access. Complete privacy and comfort.

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Villa il Promontorio Star

Villa il Promontorio

Punta Molara, Sardinia Map

  • People 12
  • Beds 8
  • Showers 8

Stunning villa carefully set into a unique location and offering unrivalled views. Its name, Villa il Promontorio, can’t but refer to the panoramic position: in a place like this, dreams will come true!

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Villa il Pellicano Star

Villa il Pellicano

Porto Rotondo, Sardinia Map

  • People 18
  • Beds 9
  • Showers 7

Located only meters from the white sandy beaches and the crystal clear sea, in the exclusive town of Porto Rotondo, Villa il Pellicano is a cosy house, of great elegance and offering quietness and absolute privacy.

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Villa Cristallo Star

Villa Cristallo

Stintino, Sardinia Map

  • People 14
  • Beds 7
  • Showers 7

Shed in a corner of paradise amidst nature, Villa Cristallo offers its guests complete privacy in exclusive, breath-taking surroundings.

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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