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
    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

    $1618 to $3419/night

  2. 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

  3. 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

    $1293 to $2454/night

  4. 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

    $1074 to $1854/night

  5. 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

    $990 to $1841/night

  6. 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

  7. HOUSE
    Terranova

    Terranova

    Modica, RG

    Terranova is a luxury villa with pool located on the edge of Modica, ancient, charming, baroque town on the south-east of Sicily. Majestic and elegant, this splendid newly-built villa was designed and built to provide the ultimate comfort. The...

    Pool

    $785 to $1313/night

  8. HOUSE
    Monte Amiata

    Monte Amiata

    Selva Santa Fiora, GR

    Villa Monte Amiata is a 150 year old farmhouse. It is in the heart of the Maremma area in southern Tuscany. This beautiful, hilly region has a rich artistic heritage. The villa has been carefully renovated. There is a spacious garden. The private...

    Pool Pets OK

    $726 to $947/night

  9. HOUSE
    Trulli Tra Pietre

    Trulli Tra Pietre

    Ceglie Messapica, BR

    It is a large complex of luxury Trulli (more than 200m²) with a stunning natural rock carved pool. All the rooms of the villa are equipped with individually controlled air conditioning. The living area is covered with WIFI signal. The truòòo...

    Pool

    $700 to $1128/night

  10. HOUSE
    Azzurro marino

    Azzurro marino

    Marina di Modica, RG

    Exclusive villa with private swimming pool situated in a splendid sea front position in Marina di Modica, a small seaside resort on the southern coast of Sicily. This luxury, contemporary villa boasts large, panoramic terraces and a wellness room...

    Pool

    $697 to $1902/night

  11. 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

  12. HOUSE
    Villa Pergo

    Villa Pergo

    Cortona, AR

    Villa Pergo is a beautiful stone farmhouse surrounded by olive trees and a lush garden. Near the villa is an ancient forest. The villa is located between Cortona and Trasimeno Lake on the border of Umbria and Tuscany. The private pool is slightly...

    Pool

    $688 to $837/night

  13. HOUSE
    Villa Agello

    Villa Agello

    Agello, PG

    Rustic Villa Agello, near the Trasimeno Lake, is situated at the border between Tuscan and Umbria, the two Italian regions mostly visited. The villa is a beautiful independent stone house with rectangular shape and gentle arches on the ground...

    Pool

    $686 to $1096/night

  14. HOUSE
    Trulli Oleandro

    Trulli Oleandro

    Martina Franca, TA

    The trullo is a luxury holiday mansion in Puglia. These authentic trulli are conservatively restructured in full consideration of their old charm and have been beautifully decorated. The villa has a large private swimming pool of 14x7 meters and...

    Pool

    $653 to $1237/night

  15. HOUSE
    La Villa

    La Villa

    Cisternino, BR

    Feel the sheer pulse where an ancient rural farmhouse, sea, and olive trees collide. Built to help the local peasants with the harvest. Having changed very little in the past 100 years, it remains a true and authentic experience. The Villa's...

    Pool

    $604 to $771/night

  16. HOUSE
    Le Edicole

    Le Edicole

    Ragusa, RG

    Le Edicole is a splendid villa with pool immersed in beautiful countryside, near the Donnafugata Castle, on the road that from the baroque town of Ragusa leads to the sea. This characteristic, country property has been expertly restored and...

    Pool Pets OK

    $593 to $1127/night

  17. HOUSE
    Villa Pepi

    Villa Pepi

    Rignano Sull'arno (fi), FI

    If you wish to spend some time in Tuscany in the best way possible and experience the feeling of belonging in this beautiful spot, no other guests around, historical Villa (early 17th Century)is the place to be. The house sits high on a hill in...

    Pool Pets OK

    $585 to $998/night

  18. HOUSE
    Profumoriente

    Profumoriente

    Siracusa, SR

    Splendid villa with private swimming pool situated only a few kilometres away from the charming historic centre of Syracuse and from the sea. The excellent location of the villa - just a few minutes' drive away from Syracuse historic centre - is...

    Pool

    $555 to $1051/night

  19. 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

  20. 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

  21. 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

  22. 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

  23. 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

  24. 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

  25. 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

  26. 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

  27. 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

  28. 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

  29. HOUSE
    Indian Well Home #12946

    Indian Well Home #12946

    Naples, FL

    Discover the convenience and value of Lely Resort. Amenities include a clubhouse, restaurant, and proshop, community pool and spa, walking and biking trails and fishing. This Indian Wells home features a magnificent view of the golf course from the...

    Pool
  30. HOUSE
    Villa Luminosa

    Villa Luminosa

    Cortona, AR

    Villa Luminosa is a beautiful villa in the hills near Cortona. The villa enjoys a picturesque location and is surrounded by olive groves and vineyards, typical of the Tuscan hills. From the pool you have spectacular views of Cortona. In the garden...

    Pool

    $484 to $750/night