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
    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

    $2113 to $3176/night

  2. 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 $2505/night

  3. 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

  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
    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

    $1552 to $3281/night

  6. 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

  7. 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

  8. 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

    $1243 to $2357/night

  9. 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

  10. 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

    $1205 to $1804/night

  11. 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

  12. 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

    $1031 to $1781/night

  13. 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

    $1028 to $1295/night

  14. 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

    $954 to $1770/night

  15. HOUSE
    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 $1585/night

  16. 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

  17. HOUSE
    Casa Leone

    Casa Leone

    Loreto, AN

    Casa Leone lies in a rural area, just 2.5 km from the sea and beach. The beautiful nature reserve Conero with its gorgeous coasts lies at approximately 15 km from the beach. It's a seventeenth-century farmhouse, completely renovated with attention...

    Pool Pets OK

    $891 to $1594/night

  18. HOUSE
    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 $1235/night

  19. 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

  20. 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

  21. 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

  22. 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

  23. 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 $990/night

  24. 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

    $782 to $1665/night

  25. HOUSE
    Villa Marino

    Villa Marino

    Cortona, AR

    Villa Marino is located in a perfect spot in the hills, ideal for a fun and relaxing holiday. The villa is 15 minutes walk from the famous Etruscan city of Cortona. From Cortona, you have a wonderful view over the Chiana valley. The villa is...

    Pool

    $779 to $883/night

  26. HOUSE
    Nidino

    Nidino

    Cortona, AR

    In one of the most beautiful scenery around Cortona, overlooking the Val di Chiana valley, you find Nidino. The Villa is isolated and immersed in a complete privacy and tranquility. All around the property you can admire a magnificent olive grove of...

    Pool

    $778 to $778/night

  27. 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

  28. 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

  29. 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

    $769 to $1368/night

  30. HOUSE
    Villanovia

    Villanovia

    Volterra, PI

    Villanovia is a fully renovated country property, inside a natural park, with a 360° amazing panorama. It overlooks the cities of Volterra and Pomarance, the Metallic Hills of Larderello and untouched forest and farm scenarios. The house has...

    Pool

    $765 to $1093/night