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 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

  2. 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

  3. 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

  4. VILLA
    Villa Veronica

    Villa Veronica

    Cortona, AR

    Villa nearby Cortona with private swimming pool, spacious garden, stunning views and a barbecue Villa Veronica is a fully restored farmhouse in the middle of Valdichiana close to the Etruscan city of Cortona. The area consists of cornfields and...

    Pool

    EUR598 to EUR870/night

  5. 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

  6. 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

  7. HOUSE
    Villa Celeste 8

    Villa Celeste 8

    Fiumana, FC

    Beautiful villa with annex and private swimming pool the Emilia Romagna area Villa Celeste is a beautiful and luxurious villa in the Emilia Romagna region. The villa is surrounded by a beautiful vineyard and consists of a villa and an annex with a...

    Pool

    EUR592 to EUR1,269/night

  8. VILLA
    Santa Fiora

    Santa Fiora

    Selva Santa Fiora, GR

    An attractive villa in the Maremma area. Villa Santa Fiora is a renovated farmhouse dating from 1886. It is in the heart of the Maremma area in southern Tuscany. This beautiful, hilly region has a rich artistic heritage. There is a well kept garden...

    Pool

    EUR587 to EUR736/night

  9. VILLA
    Villa Melograno

    Villa Melograno

    Arezzo, AR

    Villa with private pool on wine estate, elegant and chic decor This villa is located on a wine estate in the hills near Arezzo at 550 meters altitude. The estate consists of woods and vineyards. The owner is very environmentally conscious and the...

    Pool

    EUR585 to EUR927/night

  10. 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

  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. 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

    EUR579 to EUR1,236/night

  13. 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

  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

    EUR569 to EUR697/night

  15. VILLA
    Salinella

    Salinella

    PACECO, TP

    Comfortable villa with private pool, nearby Trapani and only 450m from the sea! Salinella is a beautiful, comfortable villa with private swimming pool situated near Trapani, ancient town at the extreme western point of Sicily. The property is set on...

    Pool

    EUR565 to EUR988/night

  16. VILLA
    Villa Giovanna

    Villa Giovanna

    Montalcino, SI

    Villa with private pool with stunning views of the Val di Orcia This delightful farm was born as an ancient Tuscan farm, the oldest part dates back to the fifteenth century we find it between Montalcino and Mount Amiata on a panoramic position, it...

    Pool

    EUR565 to EUR676/night

  17. VILLA
    Villa Valardegna

    Villa Valardegna

    Montepulciano, SI

    Rustic villa with private pool near Montepulciano, breathtaking views Villa Valardegna enjoys a wonderful location just 900 meters from the historic center of Montepulciano. The villa is an old and rustic farmhouse made of medieval stone. You can...

    Pool

    EUR559 to EUR1,336/night

  18. HOUSE
    Villa Carpaneto

    Villa Carpaneto

    Carpaneto Piacentino, PC

    Villa with private swimming pool, spacious garden and breathtaking view Villa Carpaneto is a villa with private pool and large garden in the hills of Piacenza. The garden is about 10,000 square meters and provides a breathtaking view of the hills....

    Pool

    EUR547 to EUR634/night

  19. 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

  20. HOUSE
    Villa Milivita

    Villa Milivita

    Monopoli, BA

    Renovated villa with private pool and huge garden with equipped terrace Itis a luxury mansion with four large bedrooms, featuring a saltwater swimming pool of 14x7m. The villa is sized 250m² on two levels and is situated in the peaceful...

    Pool

    EUR537 to EUR791/night

  21. VILLA
    Villa Nella

    Villa Nella

    Cortona, AR

    Typical Tuscan farmhouse with private swimming pool, 900m away from a small bar Villa Nella is a typical Tuscan farmhouse which has been beautifully restored. The villa is located in open countryside, surrounded by wheat fields and sunflowers. The...

    Pool

    EUR532 to EUR768/night

  22. HOUSE
    Casettauno

    Casettauno

    Vinci, FI

    Farmhouse between culture and nature between Pisa and Florence with private pool Set among the verdant Montalbano hills, this farm is located in the heart of Tuscany, just a few kilometres from the most beautiful and striking places in the region....

    Pool

    EUR530 to EUR847/night

  23. VILLA
    Villa Ambra

    Villa Ambra

    Cortona, AR

    Luxury villa covered with beautiful ivy, private swimming pool, near Cortona Villa Ambra is located at 400 mt in the hills east of Cortona. The villa is surrounded by olive trees and from the villa you have a beautiful view over the whole of...

    Pool

    EUR527 to EUR708/night

  24. VILLA
    Villa Rosso

    Villa Rosso

    Badia al Pino, AR

    Tasteful villa with rose garden, swimming pool and golf training course Villa Rossa is a prestigious and tasteful villa near Arezzo. The owner has decorated the house with great passion. The villa is surrounded by a lush garden with rose bushes and...

    Pool

    EUR522 to EUR728/night

  25. VILLA
    Palazzo Antico

    Palazzo Antico

    Montepulciano, SI

    Villa surrounded by vines, on top of a hill with stunning views. This beautiful, spacious villa is surrounded by vines and is located on the top of a hill from where you can enjoy beautiful panoramas. The villa has a beautiful green garden with...

  26. 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

  27. HOUSE
    Villa Cozzo

    Villa Cozzo

    Terrasini, PA

    Beautiful luxury villa in Sicilian style with beautiful private pool and garden. Don't look any further! From this villa, you'll have a perfect holiday on this sunny island. It's a villa, completely built and arranged in Sicilian style. First of...

    Pool

    EUR517 to EUR708/night

  28. VILLA
    La Selvicciola

    La Selvicciola

    Terricciola, PI

    A typical farmhouse surrounded by vineyards and fields A typical farmhouse on "top of the hill", surrounded by vineyards and fields with a large swimming pool that reflects the warm colors of the Tuscan countryside. Ideal for a group of friends who...

    Pool

    EUR514 to EUR981/night

  29. VILLA
    Villa Federica

    Villa Federica

    Cortona, AR

    Villa with private swimming pool in the Tuscan hills, only 1 km from Cortona A few steps from the beautiful Etruscan town of Cortona, which is only 1 km from the city center, lies Villa Federica, surrounded by orchards and crops, in a strategic...

    Pool

    EUR511 to EUR723/night

  30. HOUSE
    Podere San Giovanni

    Podere San Giovanni

    Chianni, PI

    A beautiful house with breathtaking view, large private pool, near Pisa "Podere S. Giovanni is an oasis of tranquility, the old farmhouse is surrounded by the hills of Pisa and offers the opportunity to relax, take long walks, to go swimming in the...

    Pool

    EUR508 to EUR742/night