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. VILLA
    Villa Cherry

    Villa Cherry

    Cortona, AR

    Elegant villa at an altitude of 500 m in the hills, with a private swimming pool 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...

    Pool

    EUR1,239 to EUR1,431/night

  2. VILLA
    Moon

    Moon

    Fontane Bianche, SR

    Exclusive villa with private swimming pool that enjoys a splendid seafront view 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...

    Pool

    EUR1,169 to EUR1,947/night

  3. VILLA
    Boheme

    Boheme

    Taormina, ME

    Villa with sea view and private pool very near to the center of Taormina 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...

    Pool

    EUR970 to EUR1,676/night

  4. VILLA
    Cuoricino

    Cuoricino

    Siracusa, SR

    Villa with private swimming pool and large equipped terrace for dining al fresco 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...

    Pool

    EUR896 to EUR1,664/night

  5. VILLA
    Agora

    Agora

    Agrigento, AG

    Exclusive luxury villa in Agrigento with private pool, Jacuzzi and BBQ 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...

    Pool

    EUR735 to EUR1,567/night

  6. VILLA
    Monte Amiata

    Monte Amiata

    Selva Santa Fiora, GR

    A beautiful villa in the Maremma area. 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....

    Pool

    EUR657 to EUR856/night

  7. COTTAGE
    Trulli Tra Pietre

    Trulli Tra Pietre

    Ceglie Messapica, BR

    The terrace is ideal for outside dining, the great pool is surrounded by lawn 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...

    Pool

    EUR648 to EUR1,045/night

  8. COTTAGE
    Trulli Country Golf

    Trulli Country Golf

    Gioia del Colle, BA

    Golf course, swimming pool and jacuzzi ideal for stays with family and friends 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...

    Pool

    EUR643 to EUR1,037/night

  9. VILLA
    Azzurro marino

    Azzurro marino

    Marina di Modica, RG

    Villa with private swimming pool and jacuzzi in a splendid sea front position 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...

    Pool

    EUR630 to EUR1,719/night

  10. COTTAGE
    Trulli Oleandro

    Trulli Oleandro

    Martina Franca, TA

    Private pool surrounded by greenery, the outside area is great for relaxing 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...

    Pool

    EUR605 to EUR1,146/night

  11. VILLA
    Villa Agello

    Villa Agello

    Agello, PG

    Beautiful villa with private pool 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...

    Pool

    EUR597 to EUR936/night

  12. VILLA
    Terranova

    Terranova

    Modica, RG

    luxury villa with private pool in Modica! For a relaxing holiday in Sicily 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...

    Pool

    EUR596 to EUR1,111/night

  13. VILLA
    Profumoriente

    Profumoriente

    Siracusa, SR

    Lovely luxury villa with private pool just a few km from the center of Syracuse 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...

    Pool

    EUR583 to EUR950/night

  14. HOUSE
    Villa Pergo

    Villa Pergo

    Cortona, AR

    Villa with private pool between the olive trees with garden and beautiful view 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...

    Pool

    EUR570 to EUR756/night

  15. HOUSE
    Le Edicole

    Le Edicole

    Ragusa, RG

    Beautiful villa with swimming pool surrounded by nature near Ragusa and the sea 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...

    Pool

    EUR537 to EUR1,019/night

  16. VILLA
    Villa Pepi

    Villa Pepi

    Rignano Sull'arno (fi), FI

    Set in breathtaking landscape just outside Florence with lovely garden and pool 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...

    Pool

    EUR518 to EUR933/night

  17. HOUSE
    Villa Cecanibbi

    Villa Cecanibbi

    Cecanibbi (todi), PG

    Detached house with private pool in green surroundings, near Todi 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...

    Pool

    EUR501 to EUR644/night

  18. HOUSE
    Villa Capo Passero

    Villa Capo Passero

    Portopalo Capo Passero, SR

    A dreamy house on top of a cliff at sea with private pool 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...

    Pool

    EUR500 to EUR862/night

  19. VILLA
    Dragovilla

    Dragovilla

    Donnalucata, RG

    Luxurious villa with pool and wellness area in Donnalucata, 1.4km from the sea! Dragovilla is a luxury villa with swimming pool and wellness area in Donnalucata, a popular seaside resort on the south-east of Sicily. Framed by typical dry-stone...

    Pool

    EUR495 to EUR507/night

  20. HOUSE
    La Cumbre

    La Cumbre

    Lucca, LU

    Charming and comfortable villa near Lucca with private pool 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...

    Pool

    EUR493 to EUR716/night

  21. 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
  22. 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 EUR631/night

  23. HOUSE
    Villa Cipresso

    Villa Cipresso

    Moniga del Garda, BS

    Luxury apartment with air conditioning and private swimming pool near Lake Garda Experience this semi-detached holiday home, just 1 km from Lake Garda! The house includes an enclosed garden with a beautiful lawn. You can enjoy a lovely breakfast in...

    Pool

    EUR469 to EUR626/night

  24. HOUSE
    Masseria Tarsia Incuria

    Masseria Tarsia Incuria

    Conversano, BA

    A luxurious and spacious Masseria with private pool on 1 hectare of private land 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...

    Pool

    EUR461 to EUR963/night

  25. HOUSE
    Villa Casale Vaticano

    Villa Casale Vaticano

    Monsummano Terme, PT

    Beautiful detached property with private pool and hot tub situated on the hills 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...

    Pool

    EUR457 to EUR849/night

  26. VILLA
    La Villa

    La Villa

    Cisternino, BR

    Old farmhouse, private pool and Trullis for a typical 'vacanza Pugliese' 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...

    Pool

    EUR457 to EUR697/night

  27. 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

  28. HOUSE
    Villa Mezzogiorno

    Villa Mezzogiorno

    Cortona, AR

    Magnificent villa, extremely panoramic position, sauna, jacuzzi and private pool 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...

    Pool

    EUR446 to EUR727/night

  29. HOUSE
    Villa dei Fiori

    Villa dei Fiori

    Ragalna, CT

    Beautiful house with private pool and a lovely terrace with outdoor kitchen 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,...

    Pool

    EUR446 to EUR735/night

  30. VILLA
    Casale Offida

    Casale Offida

    Offida, AP

    Villa with private swimming pool, near the Riviera delle Palme, hilly area Casale Offida is a villa with a private swimming pool a few km from the center of Offida and the famous Riviera delle Palme. This beautiful villa is located in the...

    Pool

    EUR434 to EUR647/night