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 Positano

    Villa Positano

    Positano, SA

    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 Positano. The villa has a modern style. The villa is 54 steps from the...

    Pool

    $1880 to $3395/night

  2. 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

  3. 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

  4. HOUSE
    Villa Sky meets Sea

    Villa Sky meets Sea

    Nocelle, SA

    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 villa is very special and will make your stay unforgettable. You can see...

    Pool

    $1598 to $2160/night

  5. HOUSE
    Villa Masino

    Villa Masino

    Varignana, BO

    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 vineyards, the tasteful dwelling, not only benefits from an excellent position but...

    Pool Pets OK

    $1532 to $2321/night

  6. 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

  7. 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

  8. 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

  9. HOUSE
    Boheme

    Boheme

    Taormina, ME

    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 Umberto, but also to a wealth of smart boutiques, restaurants and clubs that are...

    Pool

    $1074 to $1854/night

  10. HOUSE
    Villa Celeste 14

    Villa Celeste 14

    Fiumana, FC

    Villa Celeste is a beautiful and luxurious villa in the Emilia Romagna region. The villa is surrounded by a beautiful vineyard and consists of a villa and an annex with a panoramic swimming pool and views over Rabbi valley and the town of Forlì....

    Pool Pets OK

    $1031 to $2153/night

  11. 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

  12. 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

  13. 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

  14. 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

  15. 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

  16. HOUSE
    Villa Valardegna

    Villa Valardegna

    Montepulciano, SI

    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 easily walk to the city center via a nice route. The beautiful town of...

    Pool Pets OK

    $819 to $1478/night

  17. 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

  18. HOUSE
    Castello

    Castello

    Sarteano, SI

    Castello is a castle from 1465 on an estate in an idyllic part of Tuscany with elms, pines, vineyards and olive groves between the Val di Chiana and Val d'Orcia. The exterior of the castle is of red brick and limestone bar. The interior is...

    Pool Pets OK

    $808 to $914/night

  19. 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

  20. 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

  21. HOUSE
    Paternone

    Paternone

    Chianni, PI

    Casale PATERNONE is a combination of two farmhouses, built 30 m apart and offering the perfect solution for a large group wishing to spend time together without necessarily being on top of one another; each with its own pool. CASALE PATERNO is an...

    Pool Pets OK

    $785 to $1368/night

  22. 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

  23. HOUSE
    Villa Metauro

    Villa Metauro

    Montemaggiore al Metauro, PU

    Midway between the sea and the hinterland, surrounded by breathtaking countryside: this is the setting for Villa Tombolina, old summer residence of the Archbishops of Urbino, a picturesque relais with refined rooms and a warm, welcoming atmosphere....

    Pool Pets OK

    $773 to $1183/night

  24. 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

  25. HOUSE
    Villa Leo

    Villa Leo

    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 consists of two floors and has four...

    Pool

    $746 to $1125/night

  26. 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

  27. 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

  28. 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

  29. 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

  30. 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