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 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

  2. VILLA
    Moon

    Moon

    Fontane Bianche, SR

    Exclusive villa with private swimming pool that enjoys a splendid seafront view Exclusive villa with private swimming pool that enjoys a splendid seafront position in Fontane Bianche, a popular seaside resort south of Syracuse. Surrounded by a well...

    Pool

    EUR1,181/night

  3. 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

  4. VILLA
    Villa Positano

    Villa Positano

    Positano, SA

    Luxury villa with private pool near Positano and overlooking the sea Villa Positano is a luxury semi-detached villa with views over the sea and the coast. The villa has been completely restored and is located in a picturesque area near the town of...

    Pool

    EUR1,717 to EUR2,287/night

  5. VILLA
    Villa Mezzeria

    Villa Mezzeria

    Guardea, TR

    Luxurious villa, near Orvieto, with heated pool and private spa Villa Mezzeria is in the open countryside in southern Umbria, on a hill with panoramic views over the oasis of Alviano below, a few kilometers from the Umbrian towns such as Orvieto,...

    Pool

    EUR871 to EUR1,182/night

  6. VILLA
    Giuly

    Giuly

    Gallipoli, LE

    Wonderful villa with private pool near Gallipoli and the main beaches! Beautiful villa with private pool located in Gallipoli, just a few minutes drive from some of the most beautiful beaches of the Apulian Ionian coast. Ideal residence to enjoy a...

    Pool

    EUR1,111 to EUR3,121/night

  7. VILLA
    Boheme

    Boheme

    Taormina, ME

    Villa with sea view and private pool very near to the center of Taormina Exclusive villa with private swimming pool in Taormina. Refined and prestigious, this splendid property is situated in close proximity to the Greek Theatre and to Corso...

    Pool

    EUR980 to EUR1,418/night

  8. 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

  9. VILLA
    Villa Sole

    Villa Sole

    Macerata, MC

    Exclusive villa with pool and panoramic location on the hills of the Marche Villa Sole is a luxury property located a few kilometers from Macerata, in the heart of the Marche region. The villa has a unique location on top of a hill surrounded by...

    Pool

    EUR1,506/night

  10. 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

  11. VILLA
    Villa Sky meets Sea

    Villa Sky meets Sea

    Nocelle, SA

    Luxury villa with infinity pool, breathtaking views, a very special place If you are looking for a panoramic villa in Positano, furnished with great taste, and able to let you enjoy the beauty of the Amalfi Coast, choose Villa Sky Meets Sea. This...

    Pool

    EUR1,455 to EUR2,136/night

  12. 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 EUR1,135/night

  13. 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

  14. 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