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 Graziosa

    Villa Graziosa

    Cortona, AR

    Villa Graziosa is located in Valdichiana near the Etruscan city of Cortona. Here you can enjoy peace, quiet and privacy. Cortona is just 2 km away. The ground floor of the villa is used as a barn. The living area is on the first floor and is...

    Pool Pets OK

    $460 to $853/night

  2. HOUSE
    Casasellate

    Casasellate

    Volterra, PI

    Casa Sellate is a country house located in Volterra's countryside in Etruria's heart, at the edge of the Nature Reserve Berignone. The estate, over 200 hectare of woods, meadows and organically planted fields, is bordered by three rivers: an oasis...

    Pool Pets OK

    $452 to $826/night

  3. HOUSE
    Villa Magnifico

    Villa Magnifico

    Castiglion Fiorentino, AR

    Villa Magnifico is set on a hill with breathtaking views between the towns of Cortona and Castiglion Fiorentino. This old farmhouse has been completely restored and is now a villa to spend a holiday in peace and privacy. You have breathtaking...

    Pool Pets OK

    $446 to $553/night

  4. HOUSE
    Arangea

    Arangea

    Marsala, TP

    Beautiful villa with pool situated near Marsala, ancient town by the sea at the extreme western point of Sicily. This splendid villa features spacious, well kept interior spaces and outdoor areas. On the ground floor are a large living room with...

    Pool

    $445 to $793/night

  5. HOUSE
    Casa Dieci

    Casa Dieci

    Poppi, AR

    Casa Dieci consists of two luxurious holiday homes in a small borgo. You will therefore have access to two deluxe villas with heated swimming pool, air conditioning and Wi-fi in the Casentino Valley. Around the the picturesque, little square there...

    Pool

    $438 to $886/night

  6. HOUSE
    Villa Bottoni

    Villa Bottoni

    Ripabottoni, CB

    The house has been renovated and carefully furnished by the owner which paid special attention to the ancient details trying to keep them alive in the whole apartment. The house is built on three levels and it can accommodate up to eight guests. On...

    Pool

    $437 to $482/night

  7. HOUSE
    Villa Torre

    Villa Torre

    Pietranico, PE

    Near the tiny village Pietranico in Abruzzo is situated vacation home Torre. The oldest part of the house dates from 1709 and was rebuilt in 2014. The entire house has wifi and there is also an alarm system. The house is cozy, unique and cozy by the...

    Pool Pets OK

    $437 to $638/night

  8. HOUSE
    Angels House

    Angels House

    Tabiano Castello, PR

    This beautiful villa has a fantastic view on the countryside of the Emilian Apennines and the castle of Tabiano that you can reach in a few minutes by car or otherwise on foot, a nice walk through the nature of about 15 minutes. The villa is...

    Pool Pets OK

    $435 to $765/night

  9. HOUSE
    Trulli Fico India

    Trulli Fico India

    Ceglie Messapica, BR

    Luxury vacation home with a private pool in Puglia. It is a very well refined complex of trulli and lamie with a private 12x6 meter swimming pool set in the Ceglie Messapica countryside. This luxury private residence has been perfectly renovated...

    Pool Pets OK

    $427 to $806/night

  10. HOUSE
    Villa Berta

    Villa Berta

    Cortona, AR

    Villa Berta with private pool is located at 350 meters altitude in the hills north of the Etruscan town of Cortona. The villa is surrounded by 800 olive trees of the homeowner. The villa has been carefully restored. The barn is an old stone with the...

    Pool

    $418 to $661/night

  11. HOUSE
    Villa Vista

    Villa Vista

    Castiglion Fiorentino, AR

    Villa Vista is located in the hills at about 600 meters altitude, between the historic cities of Cortona and Castiglion Fiorentino, It is a fully independent villa with breathtaking panoramic views over the valley. It is an ideal place for people...

    Pool

    $413 to $672/night

  12. HOUSE
    Il Casolare di Valle

    Il Casolare di Valle

    Anghiari, AR

    Stay in a delightful holiday home at the Valle di Mezzo: a traditional stone farmhouse immersed in nature, where guests will enjoy a haven of peace and tranquillity. Meticulous recent reconstruction works have resulted in four apartments, all...

    Pool Pets OK

    $411 to $608/night

  13. 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

    $406 to $557/night

  14. HOUSE
    Villa Fulvio

    Villa Fulvio

    Pergola, PU

    Fulvio villa is located on a very quiet place with lots of privacy and is surrounded by beautiful countryside. The villa is decorated in a country style. A big advantage is that the villa is within walking distance of the center of Pergola. So you...

    Pool Pets OK

    $403 to $613/night

  15. HOUSE
    Villa La Commenda Nove

    Villa La Commenda Nove

    Faenza, RA

    This spacious villa with swimming pool is surrounded by a beautiful garden and is located in the outskirts of Faenza in a quiet area. The villa is equipped with every comfort and has several common areas making this villa ideal for a large family...

    Pool Pets OK

    $400 to $576/night

  16. HOUSE
    Villa Stia

    Villa Stia

    Stia, AR

    Villa Stia is a beautiful stone villa in the Casentino region, with a private pool and a well-maintained garden of 9,000 square meters. The villa is on a hill and has a sunny position. When you look out over the valley you can enjoy a stunning wiew...

    Pool Pets OK

    $388 to $597/night

  17. HOUSE
    Tenuta Mariano

    Tenuta Mariano

    Noceto, PR

    On the road between Parma and Fidenza, there is the farm with villa that stretches over a vast area of woods and hills. For racehorse enthusiasts this place represents an important piece of the recent history of international horse racing: with its...

    Pool Pets OK

    $377 to $739/night

  18. HOUSE
    Villa Verde

    Villa Verde

    Cortona, AR

    Villa Verde is a rustic farmhouse about 400 meters above sea level in the hills near Cortona. The villa is surrounded by rolling hills and offers privacy and tranquility. Thanks to a careful restoration, this old country house from the seventeenth...

    Pool Pets OK

    $363 to $706/night

  19. HOUSE
    Pignabianca

    Pignabianca

    Marusa, TP

    La Pigna Bianca is a beautiful villa with pool situated near Trapani, halfway between the nature reserve of the salt pans and the Stagnone lagoon. The property, which overlooks its lovely garden, offers - besides the swimming pool - large, panoramic...

    Pool

    $360 to $700/night

  20. HOUSE
    Villa Fano

    Villa Fano

    Isola di Fano, PU

    Villa Fano is an agriturismo. The rustic house consists of three apartments and a large dining room. It is an ideal place for families but 3 are very fond of their privacy. The farmhouse has been restored with traditional materials and the decor is...

    Pool

    $355 to $653/night

  21. HOUSE
    Villa Rita

    Villa Rita

    Monopoli, BA

    It is a bright and spacious villa with a private pool of 10x5 meters. It is located in the countryside along the hills between Monopoli and Castellana Grotte only a short drive away from the beach. The villa has been recently renovated and furnished...

    Pool

    $355 to $769/night

  22. HOUSE
    Villa Miriam

    Villa Miriam

    Cortona, AR

    Villa Miriam is located about 600 meters in the hills and has a panoramic view of the Valdichiana. This Tuscan villa with annexed hayloft has been completely restored. The villa is on a hill covered with olive trees and you can enjoy peace, quiet...

    Pool Pets OK

    $350 to $544/night

  23. HOUSE
    Fontana Tutto

    Fontana Tutto

    Monteverdi Marittimo, PI

    You are bound to enjoy yourself in this pleasant, spacious villa situated up in the hills by Monteverdi Marittimo. Enjoy the enclosed private swimming pool with outdoor shower and loungers. Start a new book on the terrace or under one of the olive...

    Pool

    $339 to $746/night

  24. HOUSE
    Villa Mimosa 2

    Villa Mimosa 2

    Corlaga, MS

    Meet this beautiful stately villa with its fresh, modern and attractive interior. Beautiful details like the wonderful mosaic floor on the upper level and French doors towards the balconies on the front and the rear. Beautiful arch passageways,...

    Pool

    $339 to $590/night

  25. HOUSE
    Agriturismo ValleFiorita

    Agriturismo ValleFiorita

    Aulla, MS

    The agriturismo is located in Northern Tuscany, about 90 km north of Pisa, in the area of ​​Cinque Terre, Portovenere, Lerici and Versilia. The agriturismo consists of three apartments, which are offered together. The agriturismo accommodates...

    Pool Pets OK

    $336 to $493/night

  26. HOUSE
    Villa Terra

    Villa Terra

    Cortona, AR

    Villa Terra is a completely renovated villa with stunning views over the valley and the nearby town of Cortona. The villa is a former farm and is surrounded by a beautiful garden with patio furniture. The villa is very attractively furnished. The...

    Pool Pets OK

    $334 to $664/night

  27. HOUSE
    Morena

    Morena

    Marsala, TP

    Beautiful, Mediterranean style villa situated just a just a stone's throw away from one of the most popular sandy beaches south of Marsala, an ancient small town located 30 kilometres from Trapani. Ideal property for those looking for a sunny,...

    $332 to $746/night

  28. HOUSE
    Piccadilly Home #16636

    Piccadilly Home #16636

    Naples, FL

    Absolutely Gorgeous 4 bedroom home located in a serene community in the center of Naples. This home features 4 bedrooms & 2.5 baths. The Master bedroom and bath are on the first level while the other 3 guest rooms are upstairs with a shared bath. A...

    Pool
  29. HOUSE
    Il Frantoio

    Il Frantoio

    Massa Lubrense, NA

    Embracing the hills of the Mediterranean countryside, this traditional country style villa is surrounded by olive groves and perched high up on the hillside of the quaint village of Sant’Agata. Comfortably accommodating up to 7 people, the villa...

    Pool

    $326 to $1,736/night

  30. HOUSE
    Villa Monti

    Villa Monti

    Montescudo, RN

    This spacious villa is equipped with every convenience and comfort. For example, each bedroom has a walk-in closet and a private bathroom. From the covered terrace you can enjoy a magnificent view over the rolling hills and the sea. In the garage...

    Pets OK

    $320 to $569/night