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 Federica

    Villa Federica

    Cortona, AR

    A few steps from the beautiful Etruscan town of Cortona, which is only 1 km from the city center, lies Villa Federica, surrounded by orchards and crops, in a strategic position from which you can enjoy a breathtaking view of the Chiana valley. This...

    Pool Pets OK

    $555 to $791/night

  2. HOUSE
    Villa Cecanibbi

    Villa Cecanibbi

    Cecanibbi (todi), PG

    Close to the Umbrian town of Todi, this charming holiday home sits amidst the lush forest and offers complete privacy—including your own personal swimming pool! The location boasts a breathtaking view of the hills; you can even see Perugia in the...

    Pool

    $553 to $712/night

  3. HOUSE
    Villa Capo Passero

    Villa Capo Passero

    Portopalo Capo Passero, SR

    Villa Capo Passero is an exclusive cliff top villa with swimming pool located a few hundred metres from the beach and the small town centre of Portopalo di Capo Passero, Sicily's southernmost point. Its large, well equipped terraces offer...

    Pool

    $553 to $953/night

  4. HOUSE
    Villa Giuliana

    Villa Giuliana

    Castiglion Fiorentino, AR

    Villa Elena with private pool is located in the middle of the Tuscan countryside and a short walk from the historic center of the beautiful town of Castiglione Fiorentino. The stone villa is surrounded by olive trees and cypresses that dominate the...

    Pool Pets OK

    $551 to $870/night

  5. HOUSE
    La Cumbre

    La Cumbre

    Lucca, LU

    Since three generations the family owns this charming 18th century farm house on the hills of the medieval city of Lucca, just beside an 11th century small white stoned facade church. The Farm has been restored and converted to a traditional...

    Pool Pets OK

    $545 to $792/night

  6. HOUSE
    Sanciro

    Sanciro

    Salemi, TP

    San Ciro is an elegant dwelling with swimming pool set in a quiet, sunny location close to Salemi, characteristic small town in the province of Trapani. The villa is surrounded by a well-tended Mediterranean garden with a splendid pool and boasts...

    Pool

    $543 to $1005/night

  7. 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

  8. HOUSE
    Crescenzio 3

    Crescenzio 3

    Roma, RM

    Apartment Crescenzio 3 is located in the prestigious Prati district, just a few meters from St. Peter's Square and the Vatican Museum. You can walk to main tourist attractions, such as Piazza di Spagna, Castel Sant'Angelo and Piazza Navona. The...

    $539 to $574/night

  9. 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

  10. 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

  11. HOUSE
    Villa Collina

    Villa Collina

    Castiglion Fiorentino, AR

    Villa Collina is an old farmhouse situated on a hill and was recently renovated. The Tuscan charm is retained by the careful renovation. The villa has terracotta tiled floors and wooden ceiling beams. The villa is surrounded by a large and well...

    Pool

    $523 to $1008/night

  12. 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

  13. HOUSE
    Villa Il Cedro

    Villa Il Cedro

    Cortona, AR

    A few steps from the beautiful Etruscan town of Cortona, rises Il Cedro, a beautiful stone building recently restored, set in a strategic position from which you can enjoy a breath-taking view of the Valdichiana. This wonderful villa with cottage...

    Pool

    $521 to $793/night

  14. HOUSE
    Villa Bianca

    Villa Bianca

    Ripatransone, AP

    Villa Bianca is immersed in the beautiful hills of Ascoli in a panoramic position in the heart of the Marche region. The villa is surrounded by a large garden with roses, fruit trees and large terracotta pots with citrus plants. Villa Bianca has...

    Pool Pets OK

    $518 to $845/night

  15. 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

  16. HOUSE
    Villa Core

    Villa Core

    Fabbri di Montefalco, PG

    Villa Marica is a charming villa with a private pool in Umbria, located near the famous town of Montefalco, known for its Sagrantino wine production. The stone farmhouse has been carefully restored giving the property a unique rural style. It will...

    Pool

    $514 to $879/night

  17. HOUSE
    La Collina Grande Completa

    La Collina Grande Completa

    Tredozio, FI

    This beautiful villa has two individual apartments, which can be hired as a whole, which makes this villa ideal for a family or group of friends who want to enjoy the peace in an apartment that is provided with every comfort. This villa is located...

    Pool Pets OK

    $513 to $871/night

  18. HOUSE
    Avane

    Avane

    Pian di Sco' (arezzo), AR

    This luxury villa at 560 meters hight, with a fantastic view is situated at the edge of the Chianti and at the foot of the Apennines, the ideal point of departure for enjoyable daytrips in the oh so typical Tuscany. Any shoppers in your company...

    Pool

    $512 to $1008/night

  19. HOUSE
    Villa America

    Villa America

    Castiglion Fiorentino, AR

    Villa America is in a beautiful location on top of a hill, a few kilometers from the bustling cities of Castiglion Fiorentino and Cortona. This old Tuscan farmhouse enjoys stunning views of the surrounding countryside and is the ideal choice for...

    Pool

    $511 to $735/night

  20. HOUSE
    Villa Sant Angiola

    Villa Sant Angiola

    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

    $508 to $950/night

  21. HOUSE
    Villa Melina

    Villa Melina

    Desenzano del Garda, BS

    Liberty style villa, built in 1917, surrounded by a fenced garden with private swimming pool (6 x 10 m) with sunbeds. Central heating and air conditioning in the double bedrooms. Portable air conditioners in the single bedrooms. The villa features...

    Pool

    $500 to $829/night

  22. HOUSE
    Masseria Tarsia Incuria

    Masseria Tarsia Incuria

    Conversano, BA

    The masseria is a 17th Century building of over 300 square meters with a large private pool of 10x6 meters. The Masseria has been tastefully furnished and offers 3 large double bedrooms and one single bedroom with a second removable single bed, but...

    Pool

    $499 to $1040/night

  23. HOUSE
    Villa Valentina

    Villa Valentina

    Cortona, AR

    Villa Valentina is a beautiful house from the seventeenth century on a hill with beautiful views over the Tuscan countryside. The villa has been completely renovated and very tastefully renovated and decorated by its owners. The stone villa has...

    Pool Pets OK

    $495 to $728/night

  24. HOUSE
    Panchevilla

    Panchevilla

    Pistoia, PT

    This villa was built in 1718 as a summer residence for the Bishop of Pistoia and Prato, as evidenced by a plaque in Latin seen in the living room. The villa is located in a green Apennine valley, less than 20km from Pistoia, well connected to...

    Pool Pets OK

    $495 to $1038/night

  25. HOUSE
    Villa dei Fiori

    Villa dei Fiori

    Ragalna, CT

    Villa dei Fiori is a beautiful dwelling with private pool in Ragalna, a characteristic village on the slopes of Mount Etna, Europe's highest and most active volcano, recently added to UNESCO's World Heritage list. Besides its lovely swimming pool,...

    Pool

    $493 to $847/night

  26. 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

  27. HOUSE
    Villa Celeste

    Villa Celeste

    Cortona, AR

    Villa Celeste is situated in open countryside between Cortona and Lake Trasimeno. The villa has a large garden with roses and other plants and is surrounded by green olive trees. The former farmhouse has been carefully restored and consists of four...

    Pool Pets OK

    $493 to $714/night

  28. HOUSE
    Villa Acqua

    Villa Acqua

    Castiglione D'orcia, SI

    This beautiful villa in the Val D'Orcia consists of 4 apartments and a spacious common living room with fireplace and kitchen of 70 square meters. The interior is cozy and typical Tuscan with hanging made tiles and wooden ceiling beams. Outside is...

    Pool Pets OK

    $491 to $851/night

  29. 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

  30. 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

    $486 to $788/night