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 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

    $1,370 to $1,583/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

    $1,293 to $2,154/night

  3. 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 $1,841/night

  4. 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 $1,734/night

  5. HOUSE
    Villa Agnese

    Villa Agnese

    Cortona, AR

    Villa Agnese is 5 km from the Etruscan city of Cortona and in the middle of the Tuscan countryside. The villa was built at the end of the nineteenth century and has been completely restored by the homeowner. The villa is tastefully decorated and the...

    Pool

    $718 to $1,021/night

  6. 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 $1,128/night

  7. 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 $1,902/night

  8. 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

    $693 to $1,118/night

  9. 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

    $679 to $1,253/night

  10. HOUSE
    Villa Collina

    Villa Collina

    Magione, PG

    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 location and offers peace and relaxation. It is a perfect place for a pleasant...

    Pool Pets OK

    $667 to $1,100/night

  11. HOUSE
    Villa Veronica

    Villa Veronica

    Cortona, AR

    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 sunflowers. The villa has wooden beams on the ceiling, brick arches, wrought iron beds and wooden...

    Pool

    $661 to $963/night

  12. 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

    $622 to $771/night

  13. HOUSE
    Villa Isabella

    Villa Isabella

    Cortona, AR

    Villa Isabella is situated in an enchanting landscape of vineyards and extensive olive groves. The villa has been carefully restored and the Tuscan charm has been preserved with wood beams and terracotta floors. You enter the villa through a large...

    Pool

    $600 to $902/night

  14. 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 $1,127/night

  15. HOUSE
    Villa Milivita

    Villa Milivita

    Monopoli, BA

    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 countryside of Monopoli in Puglia on a beautiful 10.000m² piece of land. The...

    Pool

    $579 to $1,126/night

  16. 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

  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 $698/night

  18. HOUSE
    Villa America

    Villa America

    Castiglion Fiorentino, AR

    Villa America is in a beautiful location on top of a hill, a few kilometers from the bustling cities of Castiglion Fiorentino and Cortona. This old Tuscan farmhouse enjoys stunning views of the surrounding countryside and is the ideal choice for...

    Pool

    $511 to $735/night

  19. 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 $1,040/night

  20. HOUSE
    Villa Valentina

    Villa Valentina

    Cortona, AR

    Villa Valentina is a beautiful house from the seventeenth century on a hill with beautiful views over the Tuscan countryside. The villa has been completely renovated and very tastefully renovated and decorated by its owners. The stone villa has...

    Pool Pets OK

    $495 to $728/night

  21. 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 $812/night

  22. HOUSE
    Villa Torre

    Villa Torre

    Pietranico, PE

    Near the tiny village Pietranico in Abruzzo is situated vacation home Torre. The oldest part of the house dates from 1709 and was rebuilt in 2014. The entire house has wifi and there is also an alarm system. The house is cozy, unique and cozy by the...

    Pool Pets OK

    $486 to $788/night

  23. 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
  24. 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

  25. HOUSE
    Villa White

    Villa White

    San Feliciano, PG

    Villa White is a beautiful, elegant and modern villa in the hills with private swimming pool and views over Lake Trasimeno. From the villa you have a unique view of Lake Trasimeno. The decor is tasteful with lots of light colors. The villa has a...

    Pool Pets OK

    $466 to $744/night

  26. HOUSE
    Villa Passignano

    Villa Passignano

    Passignano sul Trasimeno, PG

    Villa Passignano is located 350 meters high in the hills overlooking the Trasimeno lake. The luxury villa is set in a beautiful panoramic location and has a spacious terrace, a garden and a private swimming pool. The villa is beautifully decorated...

    Pool

    $461 to $781/night

  27. HOUSE
    Villa Graziosa

    Villa Graziosa

    Cortona, AR

    Villa Graziosa is located in Valdichiana near the Etruscan city of Cortona. Here you can enjoy peace, quiet and privacy. Cortona is just 2 km away. The ground floor of the villa is used as a barn. The living area is on the first floor and is...

    Pool Pets OK

    $460 to $853/night

  28. HOUSE
    Casasellate

    Casasellate

    Volterra, PI

    Casa Sellate is a country house located in Volterra's countryside in Etruria's heart, at the edge of the Nature Reserve Berignone. The estate, over 200 hectare of woods, meadows and organically planted fields, is bordered by three rivers: an oasis...

    Pool Pets OK

    $452 to $826/night

  29. HOUSE
    Villa Magnifico

    Villa Magnifico

    Castiglion Fiorentino, AR

    Villa Magnifico is set on a hill with breathtaking views between the towns of Cortona and Castiglion Fiorentino. This old farmhouse has been completely restored and is now a villa to spend a holiday in peace and privacy. You have breathtaking...

    Pool Pets OK

    $446 to $553/night

  30. 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 $753/night