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 Positano

    Villa Positano

    Positano, SA

    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 Positano. The villa has a modern style. The villa is 54 steps from the...

    Pool

    $1880 to $3395/night

  2. 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

  3. 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

  4. 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

  5. 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

  6. 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

  7. 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

  8. 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

  9. 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

  10. HOUSE
    Villa Albizia

    Villa Albizia

    Ossuccio, CO

    Beautiful detached villa, located in a quiet residential area, 300 meters from the lake. The villa features a large landscaped garden with lawn and flowers completely enclosed, while it offers a swimming pool and a fully equipped kitchen with table,...

    Pool Pets OK

    $670 to $1037/night

  11. 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

  12. 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

  13. 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

  14. 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

  15. 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

  16. 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

  17. 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

  18. 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

  19. 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

  20. HOUSE
    Casale Offida

    Casale Offida

    Offida, AP

    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 fascinating hilly landscape and is a perfect place for people who are looking for a...

    Pool Pets OK

    $479 to $715/night

  21. HOUSE
    Villa Allegra

    Villa Allegra

    Allerona, TR

    This luxury villa is located near the little village Allerona on the border of Tuscany and Umbria, and is 15 km from Orvieto, 100 km from Rome and 120 km from Florence. It is an ideal base for exploring and discovering the treasures of central...

    Pool

    $476 to $755/night

  22. HOUSE
    Spiga

    Spiga

    Noto, SR

    This old country estate with private pool is located at the heart of baroque Sicily, between the towns of Noto and Palazzolo Acreide (both listed as UNESCO cultural heritage). Surrounded by a large, luxuriant garden, this dwelling is a wide complex...

    Pool

    $473 to $893/night

  23. HOUSE
    Baia Riccio

    Baia Riccio

    Augusta, SR

    Baia del Riccio is a beautiful villa with outdoor Jacuzzi, in a splendid sea front location, halfway between Catania and Syracuse. Set in a quiet residential complex, the villa is surrounded by large, panoramic terraces, offering breathtaking views...

    $472 to $752/night

  24. HOUSE
    Dragovilla

    Dragovilla

    Donnalucata, RG

    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 walls, this villa offers a well-tended garden and large panoramic terraces...

    Pool

    $463 to $893/night

  25. 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

  26. HOUSE
    Vignabuona

    Vignabuona

    Acquaseria, CO

    Detached villa in a unique position, directly on the lake with pebble beach, on the most famous coast, from the tourist point of view, of Lake Como, The villa can be reached from the private parking above, closed by a gate, located on the main...

    Pets OK

    $420 to $634/night

  27. HOUSE
    Trulli la Cedrina

    Trulli la Cedrina

    Ceglie Messapica, BR

    The trulli is a luxurious holiday home in Puglia which has been carefully restored in authentic Apulian style. This luxury villa has a private infinity swimming pool with a 'beach effect' and accommodates up to 8 guests. One of the main highlights...

    Pool

    $395 to $813/night

  28. HOUSE
    Lauras

    Lauras

    Marsala, TP

    Lauras is a beautiful property with pool situated on the edge of Marsala, ancient town at the extreme western point of Sicily. Recently built, this splendid villa features spacious, well kept interior spaces and outdoor areas. On the ground floor...

    Pool

    $372 to $772/night

  29. 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

  30. HOUSE
    Villa Pergola

    Villa Pergola

    Pergola, PU

    This very stylish villa is outfitted with all kinds of luxuries, such as the massage shower, a modern kitchen, and a pool with an outdoor shower. Besides all the luxury, the house also has a very large enclosed garden with lots of privacy. You can...

    Pool Pets OK

    $349 to $585/night