Beautiful Italian holiday rentals with swimming pool

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.

View property

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!

View property

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.

View property

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.

View property

Villa Chiesanuova Star

Villa Chiesanuova

San Casciano Val di Pesa, San Casciano Val di Pesa Map

  • People 16
  • Beds 8
  • Showers 9

Wonderful Renaissance style villa located in the countryside of San Casciano in Val di Pesa, one of the most famous resort towns of the Florentine Chianti. This amazing home with swimming pool is in the middle of a magnificent estate consisting of vineyards, olive groves, and ancient trees. The property can accommodate up to 16 guests, and has 8 bedrooms and 9 bathrooms.

View property

Villa Magliano Star

Villa Magliano

Magliano in Toscana, Grosseto Map

  • People 9
  • Beds 4
  • Showers 4

Stunning villa with dependance, pool and sauna, situated near the village of Magliano in Toscana, in the Maremma area. Surrounded by a garden with lawn, olive trees and veranda, it can sleep up to 8+1 people, has 4 bedrooms and 4 bathrooms.

View property

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