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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. Villa del Gabbiano

    Villa del Gabbiano

    Porto Cervo, OT

    The villa is located in Pantogia, on a hill facing Porto Cervo and with a stunning view of the sea. The property is surrounded by a large, well-kept garden with a private swimming pool and a beautiful panoramic terrace where it's possible to dine....

    Pool

    $2908 to $2908/night

  2. Castello di Naro

    Castello di Naro

    Cagli, PU

    This special medieval castle is situated at 400 meters altitude and has a 360 degree view. It is a perfect location for a holiday in a unique holiday home with views over the hills and valleys. The castle consists of a main building, an annex and...

    Pool

    $2125 to $2125/night

  3. Borgo Verde

    Borgo Verde

    Spedalicchio, PG

    Borgo Verde is a special and atmospheric place with different rustic houses. The hamlet has a great location on top of a hill between Umbria and Tuscany. There is a spectacular 360 degree view over the rolling countryside. The homeowner has...

    Pool

    $2031 to $3183/night

  4. 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

    $1879 to $2502/night

  5. 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

    $1643 to $3277/night

  6. Taorminavilla

    Taorminavilla

    Località Mazzarò Taormina, ME

    Luxury sea front villa within the splendid setting of Taormina's Mermaid Bay. Commanding the very best location on one of the most beautiful stretches of the Mediterranean, this magnificent villa with private sea access has a breathtaking view from...

    Pool

    $1639 to $4308/night

  7. 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

    $1596 to $2158/night

  8. 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

    $1369 to $1582/night

  9. 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

    $1356 to $3281/night

  10. 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

    $1309 to $2322/night

  11. 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

    $1204 to $2250/night

  12. 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

    $1204 to $1802/night

  13. 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

    $1201 to $2357/night

  14. Villa Colline

    Villa Colline

    Cortona, AR

    Villa Collina has a breathtaking view of the hilly landscape and the Chiana Valley. You can make beautiful walks in the hills. The peace, quiet and privacy are assured in this villa. The villa was built in 1781 and completely restored in 2001. The...

    Pool

    $1075 to $1075/night

  15. Villa Olivia

    Villa Olivia

    Cortona, AR

    Villa Olivia is a spacious farmhouse in a hilly area and spectacular views. The villa is surrounded by 15 hectares of olive trees and fruit trees including pear, plum, cherry and apple trees. Cortona is 20 minutes walk away and is reached via a...

    Pool

    $1056 to $1180/night

  16. 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

    $1030 to $2151/night

  17. 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

    $990 to $1781/night

  18. 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

    $972 to $1153/night

  19. 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

    $954 to $1770/night

  20. Villa Sonia

    Villa Sonia

    Cortona, AR

    Villa Sonia is a beautiful independent property immersed in the Tuscan countryside, just a few kilometers away from the ancient city of Cortona, a small Tuscan jewel of Etruscan origin. The villa has been expertly restored by the owners who have...

    Pool

    $931 to $1584/night

  21. Villa Pianelli

    Villa Pianelli

    Collazzone, PG

    Magnificent villa with 10 bedrooms and 10 bathrooms! Ideal for a large group that wants to vacation together and looking for some luxury and privacy. You have two private pools; an outdoor pool (16 x 5 m, depth 1.40 m) and an indoor swimming pool (6...

    Pool

    $924 to $1299/night

  22. 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

    $910 to $1302/night

  23. Villa Giuseppina

    Villa Giuseppina

    Montanare, AR

    Villa Giuseppina consists of a rustic villa and charming cottage. It is a fantastic place to spend. A week with your family or friends. Some guests describe Villa Giuseppina like a piece of heaven on earth. You'll experience the real Tuscan life...

    Pool

    $892 to $1292/night

  24. Villa Elfi

    Villa Elfi

    Cortona, AR

    Villa Torre Elfi nestles in the green Tuscan countryside. The villa is surrounded by olive trees and cypresses. It is just four kilometres from the famous Etruscan city of Cortona. The villa and its tower date from the 14th century. The former...

    Pool

    $888 to $1244/night

  25. Capo d'Orso

    Capo d'Orso

    Palau, OT

    This highly elegant villa has a stunning view out across the sea and has every possible luxury. You have your own large, private pool, a carefully tended and completely enclosed garden, table tennis and a covered patio with BBQ. You can relax with a...

    Pool

    $884 to $884/night

  26. Vistabuena

    Vistabuena

    Letojanni, ME

    Vistabuena is an exclusive villa with private swimming pool situated in a splendid panoramic location, in the vicinity of Taormina. Majestic and elegant, the property offers enchanting views towards the bay of Isola Bella and the sea. This scenery,...

    Pool

    $875 to $875/night

  27. 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

    $868 to $1266/night

  28. Villa Azzurra

    Villa Azzurra

    Cortona, AR

    Immersed in the heart of Tuscany, a few steps away from the ancient Etruscan town of Cortona, Villa Azzurra is a place where you can experience an unforgettable experience. The villa is in a private location away from the noise and has been built...

    Pool Pets OK

    $849 to $1234/night

  29. 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

    $811 to $1478/night

  30. 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

    $811 to $917/night