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
    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

  3. 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

    $1547 to $2321/night

  4. 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

  5. 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

  6. 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

  7. 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

  8. 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

  9. 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

  10. 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

  11. 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

  12. 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

  13. 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

  14. HOUSE
    Villa Giovanna

    Villa Giovanna

    Montalcino, SI

    This delightful farm was born as an ancient Tuscan farm, the oldest part dates back to the fifteenth century we find it between Montalcino and Mount Amiata on a panoramic position, it is located within the national park of Val d'Orcia, Unesco...

    Pool Pets OK

    $627 to $748/night

  15. HOUSE
    Ninfea

    Ninfea

    Gratillon Saint Nicolas, AO

    Beautiful apartment in a chalet located in a historic village a few kilometers from Aosta.Spacious,elegant and refined. Furnished with style and care of every detail.Charming and elite with lovely parquet floors and heated by warm colours. An...

    $540 to $556/night

  16. HOUSE
    Villa Angeli

    Villa Angeli

    Santa Maria Degli Angeli, PG

    Villa Angeli is a charming country house in the heart of an area of outstanding natural beauty. The villa is surrounded by land and enjoys enchanting views of the world famous city of Assisi. The city is a UNESCO world heritage site. The villa is...

    Pool

    $532 to $792/night

  17. HOUSE
    Corte Dorata

    Corte Dorata

    Scicli, RG

    Corte Dorata is a beautiful country villa with swimming pool situated on the edge of Scicli, a charming baroque town and a UNESCO world heritage site. A wonderful rural landscape, characterized by olive, carob trees and white stone walls, frame the...

    Pool

    $532 to $933/night

  18. HOUSE
    Villa Maremma

    Villa Maremma

    Grosseto, GR

    Villa Maremma is a beautiful villa in the Maremma region on a hill and is surrounded by beautiful vineyards. There is a beautiful 360 degree view of the sea to the green of the Maremma region. The villa is light, elegant, comfortable and decorated...

    Pool Pets OK

    $522 to $1216/night

  19. HOUSE
    Il Giglio 18

    Il Giglio 18

    Montefiascone, VT

    The Villa is situated on top of a green hill with a lovely view over Lake Bolsena and the valleys and surrounding hills of Tuscia, in Tuscany and Umbria, a short distance from Montefiascone town. The villa has been recently restored and tastefully...

    Pool

    $515 to $833/night

  20. HOUSE
    Villa Mezzogiorno

    Villa Mezzogiorno

    Cortona, AR

    Villa Mezzogiorno is the perfect place for an unforgettable experience! This magnificent property is situated in the heart of the hills of Cortona, in an extremely panoramic position that will offer your eyes all the spectacular splendor of the lush...

    Pool Pets OK

    $493 to $803/night

  21. HOUSE
    Villa Casale Vaticano

    Villa Casale Vaticano

    Monsummano Terme, PT

    Beautiful independent villa with private pool located in the hills of Montecatini Terme with stunning views over the Tuscan hills. The recently renovated Villa looks like a 'friendly' country house equipped with the most modern amenities. Outside...

    Pool

    $490 to $905/night

  22. HOUSE
    Villa Acropolis 17

    Villa Acropolis 17

    Anzio, RM

    Villa Acropolis is a very special villa with pool in classic style. The villa is located in the countryside near the town of Anzio, a famous seaside resort south of Rome. The villa is special and tastefully decorated by the owner and the garden and...

    Pool Pets OK

    $456 to $781/night

  23. HOUSE
    Gualtierottivillino

    Gualtierottivillino

    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

    $442 to $1013/night

  24. HOUSE
    Villa Sangiovese

    Villa Sangiovese

    Trequanda, SI

    Villa Sangiovese is composed of two apartments on the first floor of a rustic house. The villa is on an estate in the beautiful and unspoilt Tuscan countryside south of Chianti, between the Crete Senesi and the Val d'Orcia. The ground floor of the...

    Pool Pets OK

    $424 to $749/night

  25. HOUSE
    Il Giglio 12

    Il Giglio 12

    Montefiascone, VT

    Villa il Giglio is situated on top of a green hill with a lovely view over Lake Bolsena and the valleys and surrounding hills of Tuscia, in Tuscany and Umbria, a short distance from Montefiascone town. The villa has been recently restored and...

    Pool

    $396 to $716/night

  26. HOUSE
    Borgo Gallinaio Glicine

    Borgo Gallinaio Glicine

    Camaiore, LU

    This very charming and beautifully finished apartment has been lovingly decorated, and it shows. The house is located on a lovely and spaciously laid out domain of 3 ha. The grounds are home to a total of 8 holiday homes and apartments. The...

    Pool Pets OK

    $385 to $511/night

  27. HOUSE
    Santo Vento

    Santo Vento

    San Fratello, ME

    The family had the dream to revive their old houses from 1820. They built this farm at the foot of the mountain, an oasis of calm and relaxation. It is situated on the edge of the beautiful Nebrodi Park at an altitude of 450 m, the sea is only 10...

    Pool

    $368 to $557/night

  28. HOUSE
    Villa Carina

    Villa Carina

    Serra san Quirico, AN

    Villa Carina is a converted farmhouse set in about a hectare of gardens, orchard and woods. The villa has been fully restored, and looks out over a beautiful valley of fields, vineyards and historic hill-top villages. Up to 18 people can be...

    Pool

    $345 to $737/night

  29. HOUSE
    Scopetorchio

    Scopetorchio

    Molazzana, LU

    Tourist residential complex, located in Garfagnana, in the Apuane Alp park, province of Lucca, a characteristic Tuscan town. Nestled among luxuriant vegetation, it is the perfect place for those looking for a relaxing break in contact with nature....

    Pool Pets OK

    $333 to $662/night

  30. HOUSE
    Campli

    Campli

    Sant'omero, TE

    This charming villa is located in a hilly area in the north of the Abruzzo region and 11 km from the sea. From the villa you have a beautiful view of the surrounding hills and the valley and the Gran Sasso, the highest peak of the Apennines. The...

    Pool Pets OK

    $305 to $776/night