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.

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  1. HOUSE
    Villa Dominick

    Villa Dominick

    Positano, SA

    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 is the hotel of the house owner. You can use the swimming pool,...

    Pool

    $1645 to $3280/night

  2. HOUSE
    Giuly

    Giuly

    Gallipoli, LE

    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 holiday of sun, sea and entertainment, but also of culture, Giulia is a...

    Pool

    $1618 to $3419/night

  3. HOUSE
    Villa Cherry

    Villa Cherry

    Cortona, AR

    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 meters above sea level. You can spend an unforgettable holiday at this place. The...

    Pool

    $1370 to $1583/night

  4. HOUSE
    Moon

    Moon

    Fontane Bianche, SR

    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 kept garden with lawn, this prestigious property offers spacious, well equipped...

    Pool

    $1293 to $2454/night

  5. HOUSE
    Villa Sole

    Villa Sole

    Macerata, MC

    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 green fields, where you can enjoy a splendid view that goes from the beach on...

    Pool Pets OK

    $1205 to $2253/night

  6. HOUSE
    Cuoricino

    Cuoricino

    Siracusa, SR

    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 relaxing holiday, in a quiet location but near the sea, providing the perfect...

    Pool

    $990 to $1841/night

  7. HOUSE
    Villa Mezzeria

    Villa Mezzeria

    Guardea, TR

    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, Todi and Amelia. The structure, is a precious villa of 500 sqm...

    Pool Pets OK

    $905 to $1295/night

  8. HOUSE
    Villa Gioia

    Villa Gioia

    Filottrano, MC

    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 villa is surrounded by nature and a park that is ideal for walks in the...

    Pool

    $902 to $1499/night

  9. HOUSE
    Villa Limonaia

    Villa Limonaia

    Sinalunga, SI

    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 situated a villa with private pool and a beautiful rural house with several apartments,...

    Pool

    $900 to $1077/night

  10. HOUSE
    Gualtierottivilla

    Gualtierottivilla

    Pistoia, PT

    The Villa is an enchanting destination in the heart of unspoiled nature, a place where time has stopped and it is easy to appreciate the charm and tranquility, perhaps relaxing in the private swimming pool, surrounded by beautiful modern sculptures...

    Pool Pets OK

    $832 to $1211/night

  11. HOUSE
    Agora

    Agora

    Agrigento, AG

    Exclusive villa with private swimming pool near Agrigento and the Valley of the Temples, majestic archaeological area listed as a World Heritage site. Ideal property for those seeking privacy, comfort and relaxation, this villa is set in a pleasant...

    Pool

    $813 to $1734/night

  12. HOUSE
    Villa Favorita Grande

    Villa Favorita Grande

    Meina, NO

    Historical villa with beautiful, classic interior, providing guests with a holiday in style. This villa is within walking distance from Lake Maggiore. You can avail of the facilities (private beach and a small harbour with a jetty) of nearby...

    Pool

    $809 to $1057/night

  13. HOUSE
    Villa San Luigi

    Villa San Luigi

    Terricciola, PI

    A beautiful Tuscan farmhouse and a large swimming pool and relaxing near oak and cypress trees, lush vineyards and olive groves. Ideal for a large family or group of friends can relax in complete privacy in "exclusive swimming pool or cook in"...

    Pool Pets OK

    $791 to $1367/night

  14. HOUSE
    Terranova

    Terranova

    Modica, RG

    Terranova is a luxury villa with pool located on the edge of Modica, ancient, charming, baroque town on the south-east of Sicily. Majestic and elegant, this splendid newly-built villa was designed and built to provide the ultimate comfort. The...

    Pool

    $785 to $1313/night

  15. HOUSE
    Villa delle Rose

    Villa delle Rose

    Mondavio, PU

    Villa delle Rose is located near Mondavio in the province of Pesaro-Urbino. It is a beautiful villa. You have a fantastic view over the surrounding countryside and the village of Mondavio. The villa is distributed over three floors, connected by an...

    Pool Pets OK

    $776 to $1221/night

  16. HOUSE
    Villa L'Oasi

    Villa L'Oasi

    Massa Lubrense, NA

    Villa L'Oasi offers stunning views of the sea and is a little paradise. An exclusive villa with lots of privacy, situated in Nerano on the Sorrento peninsula. Nerano is a traditional fishing village near Massa Lubrense on the tip of the famous...

    Pool Pets OK

    $759 to $1207/night

  17. HOUSE
    Monte Amiata

    Monte Amiata

    Selva Santa Fiora, GR

    Villa Monte Amiata is a 150 year old farmhouse. It is in the heart of the Maremma area in southern Tuscany. This beautiful, hilly region has a rich artistic heritage. The villa has been carefully renovated. There is a spacious garden. The private...

    Pool Pets OK

    $726 to $947/night

  18. HOUSE
    Villa Acropolis

    Villa Acropolis

    Anzio, RM

    Villa Acropolis is a very special villa with pool in classical style located in the Anzio countryside and its well known seaside resort located in the south of Rome. Villa Acropolis is equipped with a host of amenities and is equipped to provide...

    Pool Pets OK

    $718 to $1118/night

  19. HOUSE
    Villa Agnese

    Villa Agnese

    Cortona, AR

    Villa Agnese is 5 km from the Etruscan city of Cortona and in the middle of the Tuscan countryside. The villa was built at the end of the nineteenth century and has been completely restored by the homeowner. The villa is tastefully decorated and the...

    Pool

    $718 to $1021/night

  20. HOUSE
    Trulli Tra Pietre

    Trulli Tra Pietre

    Ceglie Messapica, BR

    It is a large complex of luxury Trulli (more than 200m²) with a stunning natural rock carved pool. All the rooms of the villa are equipped with individually controlled air conditioning. The living area is covered with WIFI signal. The truòòo...

    Pool

    $700 to $1128/night

  21. HOUSE
    Azzurro marino

    Azzurro marino

    Marina di Modica, RG

    Exclusive villa with private swimming pool situated in a splendid sea front position in Marina di Modica, a small seaside resort on the southern coast of Sicily. This luxury, contemporary villa boasts large, panoramic terraces and a wellness room...

    Pool

    $697 to $1902/night

  22. HOUSE
    Trulli Country Golf

    Trulli Country Golf

    Gioia del Colle, BA

    Wonderful complex made up by 11 rural ancient trulli with a big swimming pool (14x7 mt) and a Pitch & Putt nine-holes amateur golf course, fully illuminated also for the night game. The trulli are perfectly restored and equipped with lovely...

    Pool

    $694 to $1118/night

  23. HOUSE
    Villa Agello

    Villa Agello

    Agello, PG

    Rustic Villa Agello, near the Trasimeno Lake, is situated at the border between Tuscan and Umbria, the two Italian regions mostly visited. The villa is a beautiful independent stone house with rectangular shape and gentle arches on the ground...

    Pool

    $686 to $1096/night

  24. HOUSE
    Podere San Giovanni ventisei

    Podere San Giovanni ventisei

    Chianni, PI

    "Podere S. Giovanni is an oasis of tranquility, the old farmhouse is surrounded by the hills of Pisa and offers the opportunity to relax, take long walks, to go swimming in the lovely pool and at the same time it is really close to many cultural...

    Pool Pets OK

    $671 to $961/night

  25. HOUSE
    Villa Albizia

    Villa Albizia

    Ossuccio, CO

    Beautiful detached villa, located in a quiet residential area, 300 meters from the lake. The villa features a large landscaped garden with lawn and flowers completely enclosed, while it offers a swimming pool and a fully equipped kitchen with table,...

    Pool Pets OK

    $670 to $1037/night

  26. HOUSE
    Villa Collina

    Villa Collina

    Magione, PG

    Villa Collina is a rustic villa and dependance with private swimming pool in the rolling hills with breathtaking views over Lake Trasimeno. The villa has a beautiful location and offers peace and relaxation. It is a perfect place for a pleasant...

    Pool Pets OK

    $667 to $1100/night

  27. HOUSE
    Villa Veronica

    Villa Veronica

    Cortona, AR

    Villa Veronica is a fully restored farmhouse in the middle of Valdichiana close to the Etruscan city of Cortona. The area consists of cornfields and sunflowers. The villa has wooden beams on the ceiling, brick arches, wrought iron beds and wooden...

    Pool

    $661 to $963/night

  28. HOUSE
    Trulli Oleandro

    Trulli Oleandro

    Martina Franca, TA

    The trullo is a luxury holiday mansion in Puglia. These authentic trulli are conservatively restructured in full consideration of their old charm and have been beautifully decorated. The villa has a large private swimming pool of 14x7 meters and...

    Pool

    $653 to $1237/night

  29. HOUSE
    Santa Fiora

    Santa Fiora

    Selva Santa Fiora, GR

    Villa Santa Fiora is a renovated farmhouse dating from 1886. It is in the heart of the Maremma area in southern Tuscany. This beautiful, hilly region has a rich artistic heritage. There is a well kept garden and a swimming pool which offers...

    Pool Pets OK

    $650 to $814/night

  30. HOUSE
    Villa Melograno

    Villa Melograno

    Arezzo, AR

    This villa is located on a wine estate in the hills near Arezzo at 550 meters altitude. The estate consists of woods and vineyards. The owner is very environmentally conscious and the wines are organic. The villa has two floors and is very elegant...

    Pool

    $647 to $1025/night