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.
  1. VILLA
    Villa Positano

    Villa Positano

    Positano, SA

    Luxury villa with private pool near Positano and overlooking the sea 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...

    Pool

    EUR1,700 to EUR2,263/night

  2. VILLA
    Villa Collina

    Villa Collina

    Magione, PG

    Luxury villa with private swimming pool, sauna and emotional shower, near lake Villa Collina is a rustic villa and dependance with private swimming pool in the rolling hills with breathtaking views over Lake Trasimeno. The villa has a beautiful...

    Pool

    EUR603 to EUR995/night

  3. VILLA
    Villanovia

    Villanovia

    Volterra, PI

    Roomy and comfortable house with beautiful views and pool for refreshment 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...

    Pool

    EUR609 to EUR905/night

  4. HOUSE
    Villa Rita

    Villa Rita

    Monopoli, BA

    Gated villa with private pool in the hills of Monopoli and Castellana Grotte 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...

    Pool

    EUR329 to EUR456/night

  5. VILLA
    Franciacorta

    Franciacorta

    Villa Pedergnano - Erbusco, BS

    In the heart of Franciacorta and close by the lake, with patio and garden Elegant villa divided into two large apartments, one of which is occupied by the owner's family. The other unit is for guests and is equipped with a porch and a garden with...

    EUR138 to EUR165/night

  6. VILLA
    Villa Passignano

    Villa Passignano

    Passignano sul Trasimeno, PG

    Luxurious villa with private pool and panoramic views over Lake Trasimeno Villa Passignano is located 350 meters high in the hills overlooking the Trasimeno lake. The luxury villa is set in a beautiful panoramic location and has a spacious terrace,...

    Pool

    EUR417 to EUR706/night

  7. VILLA
    Villa San Ippolito

    Villa San Ippolito

    Sant'ippolito, PU

    Beautiful stone villa with heated pool in the hills close to the sea Villa San Ippolito is a rustic stone villa with heated swimming pool in the hills at 240 metres altitude, nearby the Adriatic sea. The villa is set in 20,000 m2 grounds and...

    Pool

    EUR227 to EUR547/night

  8. VILLA
    Villa Vista

    Villa Vista

    Castiglion Fiorentino, AR

    Villa with private swimming pool and garden, panoramic view over the valley 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...

    Pool

    EUR397 to EUR608/night

  9. VILLA
    Villa San Luigi

    Villa San Luigi

    Terricciola, PI

    A beautiful Tuscan farmhouse and a large swimming pool and relaxing 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...

    Pool

    EUR722 to EUR1,236/night

  10. VILLA
    Villa Savino

    Villa Savino

    Monte san Savino, AR

    Villa con piscina nel cuore della campagna Toscana a Monte San Savino Saviano villa is located in the Chiana Valley, known for its hilly landscape and traditional villages. Arezzo is easily accessible and is about 20 kilometers away. The villa is on...

    Pool

    EUR252 to EUR641/night

  11. VILLA
    Villa Cella

    Villa Cella

    Monte san Savino, AR

    Villa con piscina nel cuore della campagna Toscana a Monte San Savino Villa Cella lies in the Chiana valley and has a private pool and jacuzzi. The house sits on a hill about 1.5 km from the center of Monte San Savino. You have a beautiful panorama...

    Pool

    EUR213 to EUR356/night

  12. VILLA
    Panchevilla

    Panchevilla

    Pistoia, PT

    Exclusive villa surrounded by peaceful Pistoia, with private pool and spa! 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...

    Pool

    EUR448 to EUR938/night

  13. COTTAGE
    Casale Castiglione

    Casale Castiglione

    Castiglione di Garfagnana, LU

    Cozy house with private pool and breathtaking views of the Garfagnana area The farmhouse is entirely handmade in stone and dates back to the late 1700. The structure faces South so you have the sun all for yourselves from 07.00 in the morning. You...

    Pool

    EUR216 to EUR331/night

  14. HOUSE
    Corte Dorata

    Corte Dorata

    Scicli, RG

    Beautiful villa with pool near the very charming Baroque town of Scicli 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...

    Pool

    EUR481 to EUR590/night

  15. VILLA
    Villa Rigo

    Villa Rigo

    Celle sul Rigo, SI

    Villa with private pool between olive groves, near Celle sul Rigo The villa consists of two apartments connected by an internal door. There is a spacious garden and a private pool. The villa is simply furnished and from the kitchen you can look out...

    Pool

    EUR281 to EUR531/night

  16. FARMHOUSE
    Echifaldo

    Echifaldo

    Ciolino Resuttano, PA

    Comfortable holiday farm, surrounded by the pleasures and smells of nature Between the hills of the Parco delle Madonie, in Sicily, is a country house from the eighteenth century. The attention to detail was restored and furnished as a holiday farm,...

    Pool

    EUR193 to EUR240/night

  17. HOUSE
    Generosa

    Generosa

    Guistrigona-Siena, SI

    Small estate with shared swimming pool between the magnificent, Tuscan hills The small and very homely estate is located near Siena (12 km) to the edge of the Chianti and Siena in the hills, a peaceful landscape. Arezzo, Colle Val d 'Elsa, Volterra,...

    Pool

    EUR238 to EUR356/night

  18. VILLA
    Villa delle Rose

    Villa delle Rose

    Mondavio, PU

    Beautiful villa with swimming pool and hot tub, near the beach of Fano 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...

    Pool

    EUR702 to EUR1,104/night

  19. VILLA
    Villa Acropolis 17

    Villa Acropolis 17

    Anzio, RM

    Spacious villa with pool and jacuzzi in the countryside of Anzio 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...

    Pool

    EUR412 to EUR707/night

  20. HOUSE
    Paternone

    Paternone

    Chianni, PI

    Two beautifully restored farmhouses with swimming pool in the hills of Pisa 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...

    Pool

    EUR710 to EUR1,120/night

  21. COTTAGE
    Prati Due

    Prati Due

    Lierna, LC

    Spacious and comfortable ground floor apartment, nearby Lake Como This spacious and comfortable, 120 m ground floor apartment is located in the charming little town of Lierna, on the banks of Lake Como. The high quality furnishings are brand new and...

    Pool

    EUR196 to EUR332/night

  22. COTTAGE
    Tabecalla

    Tabecalla

    Bellamonte, TN

    Apartment in a typical baita in the Dolomites with sauna and Turkish bath This beautiful and rustic baita situated between the green of the fields and woods near the village of Bella Monte. The baita is surrounded by a beautiful landscape...

    EUR332 to EUR635/night

  23. HOUSE
    Allodola

    Allodola

    Castiglion Fiorentino, AR

    Cosy house in natural surroundings near the Chianti valley This pleasant apartment is part of a beautiful agriturismo with a total of 8 apartments and 1 detached house. The apartment has authentic and cosy furnishings. Together with the other...

    Pool

    EUR77 to EUR137/night

  24. HOUSE
    Michelangelo

    Michelangelo

    Gambassi Terme, FI

    Apartment in a villa with swimming pool in the middle of a beautiful landscape This apartment is located in a beautiful villa with a shared swimming pool, with a garden where you can enjoy a good local wine and enjoy the sunset. There are 3 other...

    Pool

    EUR76 to EUR119/night

  25. HOUSE
    Agriturismo Foiano Tabaccaia

    Agriturismo Foiano Tabaccaia

    Castiglion Fiorentino, AR

    Nice and cozy apartment in a natural environment near the Chianti Valley This pleasant apartment is part of a beautiful agriturismo with a total of 8 apartments and 1 detached house. The apartment has authentic and cosy furnishings. Together with...

    Pool

    EUR111 to EUR203/night

  26. HOUSE
    Urano

    Urano

    Ribera, AG

    Small and sunny residence in panoramic location near the sea. Small and sunny residence in panoramic location near the sea. From the pool and from all accommodations you can enjoy the beautiful panorama of the main attraction of Borgo Bonsignore:...

    Pool

    EUR97 to EUR176/night

  27. VILLA
    Villa Torretta

    Villa Torretta

    Baveno, VB

    Villa with pool, facing the lake, in a unique location with beautiful views This elegant, exclusive villa is located in the most famous section of the Lake Maggiore shoreline, opposite the Borromean Islands; the villa is distributed over 4 floors,...

    Pool

    EUR585 to EUR1,113/night

  28. ESTATE
    Il Portico Sette

    Il Portico Sette

    Monselice, PD

    Wonderful castle just 25 km from Padua and 65 km from Venice Recently restored and furnished with antique furniture, this elegant apartment (80 m) is located on the ground floor. There is a large, private terrace affording marvellous views over the...

    Pool

    EUR330/night

  29. FARMHOUSE
    Margherita

    Margherita

    Montepulciano, SI

    Agriturismo with swimming pool and view over vineyard Vino Nobile di Montepulciano Near the medieval town of Montepulciano is a beautiful winery with eight apartments and a swimming pool. The agriturismo is located in the rolling hills of grain...

    Pool

    EUR89 to EUR113/night

  30. APARTMENT
    Yachting Residence- Bilo Classic

    Yachting Residence- Bilo Classic

    Lavena Ponte Tresa, Lombardia

    Apartment in a newly built luxury residence, facing the lake, with swimming pool Prestigious residence, the result of the complete renovation, completed in 2017, of an old factory, overlooking Lake Lugano just a short distance from the center of...

    Pool

    EUR165 to EUR229/night