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
    Nicchia

    Nicchia

    Guistrigona-Siena, SI

    The small and very homely estate is located near Siena (12 km) on the edge of the Chianti in the hills, a peaceful landscape. Arezzo, Colle Val d 'Elsa, Volterra, San Gimignano, Assisi, Florence and the Mediterranean Sea are about an hour away from...

    Pool Pets OK

    $485 to $785/night

  2. 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
  3. 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

  4. HOUSE
    Villa Bottoni

    Villa Bottoni

    Ripabottoni, CB

    The house has been renovated and carefully furnished by the owner which paid special attention to the ancient details trying to keep them alive in the whole apartment. The house is built on three levels and it can accommodate up to eight guests. On...

    Pool
  5. HOUSE
    Villa Boschetto

    Villa Boschetto

    Proceno, VT

    This characteristic agriturismo, housing four apartments and a swimming pool, is situated in a hilly region in the Tuscia area, the land of the ancient Etruscans. The agriturismo is located on a 420 meter high hill and offers fine views across the...

    Pool Pets OK

    $482 to $651/night

  6. HOUSE
    MonteGiulia

    MonteGiulia

    Ghizzano Peccioli, PI

    You will stay on a beautiful Tuscan estate. From your private garden, you'll reach the loggia through a robust stone staircase. Inside the homes, the terracotta floors and beamed ceilings will immediately draw your attention, just like the large...

    Pool Pets OK

    $481 to $687/night

  7. 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

  8. 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

  9. HOUSE
    Villa Nella

    Villa Nella

    Cortona, AR

    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 house consists of two floors and an external staircase leads to the upper floor....

    Pool

    $473 to $600/night

  10. 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

  11. 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

  12. HOUSE
    La Contea

    La Contea

    Rosello, CH

    Apartment La Contea is the largest of the five apartments located in Castle Giuliopoli. This luxury apartment is on two floors. One bedroom is located in the tower with fireplace, panoramic views and private terrace with sunbeds. On the other floor...

    Pool

    $471 to $516/night

  13. HOUSE
    Casa de Poi

    Casa de Poi

    Salsomaggiore Terme, PR

    This beautiful villa has a fantastic view on the countryside of the Emilian Apennines and the castle of Tabiano that you can reach in a few minutes by car or otherwise on foot, a nice walk through the nature. The villa is surrounded by a large...

    Pool Pets OK

    $470 to $1065/night

  14. HOUSE
    Chalet Antey Grande

    Chalet Antey Grande

    Antey-Saint-Andrè, AO

    The chalet is situated in a quiet and sunny area of Antey Saint André, at short distance from the famous ski area of Breuil-Cervinia, were you can ski also in summer on the glacier of Plateau Rosa, above Cervinia. The apartment is fully renovated...

    Pets OK

    $466 to $1464/night

  15. 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

  16. 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

  17. HOUSE
    Acquaviva Intero

    Acquaviva Intero

    Montescudaio, PI

    Typical Tuscan farmhouse with stone façade, surrounded by several hectares of vineyards belonging to the farmhouse, located in a peaceful and sunny area just 2 Km from the town of Montescudaio, an ancient village set on a hill overlooking the sea...

    Pool Pets OK

    $461 to $1339/night

  18. 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

  19. HOUSE
    Villa Beatrice

    Villa Beatrice

    Assisi, PG

    Villa Beatrice is a villa with a large garden with trees and private swimming pool in the pretty village of Petrignano d'Assisi. Access to the villa is through a gate and a driveway. There is a terrace with a pergola, an ideal place to enjoy your...

    Pool

    $460 to $629/night

  20. HOUSE
    Villa Tuoro

    Villa Tuoro

    Tuoro sul Trasimeno, PG

    Villa Tuoro is 700 meters high on the border between Tuscany and Umbria. The villa is set in the hills and has beautiful views over Trasimeno lake. It is a pristine place just minutes from the beaches of the lake and a short distance from the most...

    Pool Pets OK

    $460 to $1085/night

  21. 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

  22. HOUSE
    Villa Acropolis 17

    Villa Acropolis 17

    Anzio, RM

    Villa Acropolis is a very special villa with pool in classic style. The villa is located in the countryside near the town of Anzio, a famous seaside resort south of Rome. The villa is special and tastefully decorated by the owner and the garden and...

    Pool Pets OK

    $456 to $781/night

  23. 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

  24. HOUSE
    Villa Marcy

    Villa Marcy

    Marciano Della Chiana, AR

    Villa Marcy is situated on a hill with olive trees in the heart of the Chiana Valley in Tuscany, near Marciano della Chiana, a medieval town. From the villa you have a panoramic view of the Val di Chiana and you can see the beautiful Cortona,...

    Pool Pets OK

    $451 to $1073/night

  25. HOUSE
    Dei Medici

    Dei Medici

    Florence, FI

    Apartment Dei Medici is situated right in the center of Flotrence in a nice "palazzo" a 5-minute walk from the Duomo and close Gli Uffizi in Piazza della Signorina. The apartment is on the first floor and there is an elevator. From the windows in...

    Pets OK
  26. 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

  27. 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

  28. HOUSE
    Villa Cipresso

    Villa Cipresso

    Moniga del Garda, BS

    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 the morning or a cozy after-dinner chat at the picnic table. The barbecue will...

    Pool

    $444 to $693/night

  29. HOUSE
    Gualtierottivillino

    Gualtierottivillino

    Pistoia, PT

    The Villa is an enchanting destination in the heart of unspoiled nature, a place where time has stopped and it is easy to appreciate the charm and tranquility, perhaps relaxing in the private swimming pool, surrounded by beautiful modern sculptures...

    Pool Pets OK

    $442 to $1013/night

  30. HOUSE
    Villa Maestosa

    Villa Maestosa

    Cortona, AR

    Maestosa villa is located in the rolling hills of the Chiana valley near the beautiful town of Cortona. The villa is situated in an elevated position with views of the area with sunflowers, olive groves and vineyards. The interior of the villa is...

    Pool

    $440 to $729/night