Welcome to Italy! Ancient Roman architecture, impossible beauty, and the best food ever! Experience Italy’s cultural diversity -- from trendy Turin, to romantic Venice, to historic Rome, to the island Sicily. No matter where you wind up, RedAwning has many gorgeous vacation homes, villas, apartments and condos in Italy, all ready to rent with a simple, hotel-style reservation process.
  1. VILLA
    Villa Dominick

    Villa Dominick

    Positano, SA

    Villa with jacuzzi, pool and garden in Positano, beautiful view Villa Dominick is a beautiful holiday home on the Amalfi coast in Positano. The villa is a 10-minute walk from Piazza dei Mulini and from the main beach in Positano. Opposite the villa...

    Pool

    EUR1,529 to EUR2,995/night

  2. HOUSE
    Villa Amagioia

    Villa Amagioia

    Varignana, BO

    Beautiful villa in the hills of Bologna, with large garden and swimming pool. This fine and astonishingly beautiful Villa, lies surrounded by five hectares of lush private garden, where peace and privacy are guaranteed. Among olive trees and...

    Pool

    EUR1,399 to EUR2,119/night

  3. VILLA
    Villa Cherry

    Villa Cherry

    Cortona, AR

    Elegant villa at an altitude of 500 m in the hills, with a private swimming pool Villa Cherry is a charming cottage situated in a unique location. It is immersed in the hills of Cortona with stunning views and total privacy. The villa is about 500...

    Pool

    EUR1,250 to EUR1,444/night

  4. VILLA
    Cuoricino

    Cuoricino

    Siracusa, SR

    Villa with private swimming pool and large equipped terrace for dining al fresco Beautiful villa with private swimming pool situated on the Maddalena peninsula, just a little bit south of Syracuse. The villa is the ideal property for those seeking a...

    Pool

    EUR904 to EUR1,681/night

  5. HOUSE
    Villa Gioia

    Villa Gioia

    Filottrano, AN

    Luxurious villa in the countryside, close to the beaches of the Conero Villa Gioia is a beautiful and luxurious villa for an exclusive holiday with excellent privacy. It is located in the surroundings of the beautiful beaches of the Conero. The...

    Pool

    EUR824 to EUR1,369/night

  6. VILLA
    Villa Limonaia

    Villa Limonaia

    Sinalunga, SI

    Villa with private pool, tennis court and shared swimming pool in the Tuscan hills In the hills between San Gimignano and Torrita di Siena and close to Sinalunga is a special estate among olive trees, vineyards and cypress trees. The estate is...

    Pool

    EUR823 to EUR983/night

  7. VILLA
    Villa Valardegna

    Villa Valardegna

    Montepulciano, SI

    Rustic villa with private pool near Montepulciano, breathtaking views Villa Valardegna enjoys a wonderful location just 900 meters from the historic center of Montepulciano. The villa is an old and rustic farmhouse made of medieval stone. You can...

    Pool

    EUR768 to EUR1,350/night