Beautiful Italian holiday rentals with swimming pool

Villa Il Tropico Star

Villa Il Tropico

Pantelleria, Trapani Map

  • People 11
  • Beds 6
  • Showers 5

Wonderful estate with 2 swimming pools, located in the Sicilian island of Pantelleria. Surrounded by a large garden with several relax areas, the estate consists of 4 “dammusi” (typical Sicilian building). It can accommodate up to 11 people, has 6 bedrooms and 5 bathrooms.

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Villa La Pineta Star

Villa La Pineta

Acquedolci, Messina Map

  • People 8
  • Beds 4
  • Showers 5

Amazing villa with swimming pool, located in Acquedolci, a seaside resort halfway between Messina and Palermo. Surrounded by a garden with ancient olive trees and outdoor dining area, the villa can accommodate up to 8 people, has 4 bedrooms and 5 bathrooms.

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Villa Dafne Star

Villa Dafne

Acireale, Catania Map

  • People 6
  • Beds 3
  • Showers 3

Stunning villa with private swimming pool, situated close to Acireale, between the slopes of Mount Etna and the blue Ionian sea. Surrounded by a garden with orange groves and outdoor dining area, it can accommodate up to 6 people, has 3 bedrooms and 3 bathrooms.

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Villa Modica Star

Villa Modica

Marina di Modica, Ragusa Map

  • People 18
  • Beds 10
  • Showers 10

Stunning villa with pool and outdoor showers, situated in Marina di Modica (southern Sicily), a few steps from the sea. Surrounded by a large park with barbecue, the property can accommodate up to 18 people, has 10 bedrooms and 10 bathrooms.

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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 Le Cascate Star

Villa Le Cascate

Trabia, Palermo Map

  • People 22
  • Beds 10
  • Showers 9

Magnificent villa with 3 pools and hot tub, located just 50 m from the sea, near Palermo. The property consists of 4 independent buildings and is surrounded by an enchanted garden with exotic plants, play area for children, outdoor kitchen and gazebo. It can sleep up to 22 people, has 10 bedrooms and 9 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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