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
    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. 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

  7. 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

  8. HOUSE
    Villa Albizia

    Villa Albizia

    Ossuccio, CO

    Exclusive villa with swimming pool, terrace and fenced garden 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...

    Pool

    EUR605 to EUR937/night

  9. 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

    EUR600 to EUR1,111/night

  10. 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

  11. 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

  12. 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

  13. 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

  14. 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

    EUR514 to EUR697/night

  15. 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 EUR726/night

  16. 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 EUR775/night

  17. VILLA
    Sanciro

    Sanciro

    Salemi, TP

    Elegant villa with swimming pool and garden, in a quiet area close by Salemi 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...

    Pool

    EUR490 to EUR732/night

  18. 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

  19. 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

  20. 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

  21. 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

  22. VILLA
    Villa Allegra

    Villa Allegra

    Allerona, TR

    Luxury villa with private pool and beautiful decor and trendy portico 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...

    Pool

    EUR430 to EUR683/night

  23. VILLA
    Spiga

    Spiga

    Noto, SR

    Ancient countryside residence with pool, in the heart of the Baroque Sicily. 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...

    Pool

    EUR428 to EUR644/night

  24. VILLA
    Arangea

    Arangea

    Marsala, TP

    Beautiful villa with pool situated near Marsala, town by the sea 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...

    Pool

    EUR407 to EUR812/night

  25. VILLA
    Baia Riccio

    Baia Riccio

    Augusta, SR

    Gorgeous villa with whirlpool bath and breathless view, only 100m from the sea! 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,...

    EUR385 to EUR513/night

  26. VILLA
    Cicero

    Cicero

    Patti, ME

    Detached villa in an excellent location, only 200 meters from the sea! Beautiful farmhouse situated just a stone's throw away from a wide sandy beach in the vicinity of Patti, an ancient small town on the northern coast of Sicily, 60 km on the...

    EUR375 to EUR441/night

  27. VILLA
    Lauras

    Lauras

    Marsala, TP

    Wonderful villa with swimming pool nearby Marsala, just 5km from the sea! 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...

    Pool

    EUR366 to EUR699/night

  28. VILLA
    Pignabianca

    Pignabianca

    Marusa, TP

    Exclusive villa with private pool and wellness centre, only 3km from the sea! 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...

    Pool

    EUR326 to EUR514/night

  29. HOUSE
    Bella Uno

    Bella Uno

    Taormina, ME

    Exclusive residence with swimming pool, lovely views of Taormina and the sea The four luxurious apartments Isola Bella are situated in a splendid panoramic position, halfway between Taormina's historic centre and the sea. Set in a new, exclusive...

    Pool

    EUR317 to EUR849/night

  30. VILLA
    Villa Pergola

    Villa Pergola

    Pergola, PU

    Very stylish villas with all luxury, close to 3 parks 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...

    Pool

    EUR316 to EUR504/night