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 Patrizia

    Villa Patrizia

    Cortona, AR

    Characteristic villa with private pool near Cortona, beautiful surroundings Superb independent property perfectly nestled among the rolling hills surrounding the ancient Etruscan town of Cortona, Villa Patrizia is the ideal place to spend a holiday...

    Pool

    EUR274 to EUR573/night

  2. VILLA
    Villa Sara

    Villa Sara

    Fossombrone, PU

    Country Villa with private pool just a few miles from Fossombrone Located in a very quiet countryside area near the Adriatic Coast, we find Villa Sara, a delightful villa with private pool in the Marche, just a few minutes from Fossombrone. Villa...

    Pool

    EUR274 to EUR652/night

  3. VILLA
    Village Albarella V5

    Village Albarella V5

    Albarella, RO

    Apartment on a vacation island in the Gulf of Venetie The accommodation is spread throughout the island and is situated either in the Fiordi area, formed by the 50 hectare large Mare Vostrum and little inland harbours, or in the green area in the...

    Pool

    EUR274 to EUR509/night

  4. COTTAGE
    Trullo Fiore di Mare

    Trullo Fiore di Mare

    Trani, BT

    Right on a limestone cliff by the sea with private access to the blue sea Trullo Fiore di Mare is an enchanting historic holiday home with a private access to the beach. Exquisite holiday home Trullo with direct access to the sea. Trullo Fiore di...

    EUR274 to EUR748/night

  5. VILLA
    Villa Eloise

    Villa Eloise

    Spoleto, PG

    Charming Villa with swimming pool near Spoleto surrounded by beautiful hills Built in 1995, the villa lies close to wine and olive oil estates, and is moments away from wonderful Italian restaurants. It is close to historical towns and villages...

    Pool

    EUR273 to EUR415/night

  6. HOUSE
    Torre Maremma

    Torre Maremma

    Talamone, GR

    Sleeping in an ancient watchtower in a natural park with fantastic views Are you looking for adventure and privacy and have you always wanted to sleep in a tower? In that case, we can highly recommend Torre Maremma. Torre Maremma is an old...

    EUR273 to EUR320/night

  7. HOUSE
    Gatterino

    Gatterino

    Peccioli, PI

    Cosy agriturismo in Toscana with outdoor swimming pool This Agriturismo lies 30 km. North-west of Volterra. In the heart of Toscana, surrounded by the magnificent hills and situated between Florence and Arezzo you will find the village Peccioli....

    Pool

    EUR273 to EUR531/night

  8. HOUSE
    Roccone

    Roccone

    Piancastagnaio (Siena), SI

    Immersed in nature, with very spacious rooms, ideal for groups Roccone lies on the spur of a rock where it has been situated for more than a century in the middle of the nature reserve Pigelleto at the foot of Mount Amiata in the province of Siena....

    Hot Tub

    EUR272 to EUR434/night

  9. FARMHOUSE
    Leo

    Leo

    Cortona, AR

    Elegant apartment in Tuscan villa with swimming pool and garden Apartment Leo is an elegant apartment in a Tuscan villa. In total there are 4 apartments. This charming villa is at the foot of the hill and on the hillside is the Etruscan city of...

    Pool

    EUR272 to EUR329/night

  10. VILLA
    Total Nisa

    Total Nisa

    Montefiridolfi, FI

    Beautiful manor house overlooking the hills of Chianti Classico This villa, dating back to the first half of the 1900s is located in the Chianti hills, close to San Casciano in Val di Pesa. Set among lush greenery and nestled in the quiet Tuscan...

    Pool

    EUR269 to EUR385/night

  11. HOUSE
    Antigua Home #34084

    Antigua Home #34084

    Naples, FL

    Whether it’s watching the sunset from your private pool, hosting a game night in the family room or creating a meal for the family in the gourmet kitchen, relaxation is the name of the game in this stunning Marco Island vacation home. Elegance and...

    Pool

    $269 to $574/night

  12. VILLA
    Archi

    Archi

    Sinalunga, SI

    Estate with pool and tennis court in the Tuscan hills In the hills between San Gimignano and Torrita di Siena and close to Sinalunga is a special estate among olive trees, vineyards and cypress trees. The estate is situated a villa with private pool...

    Pool

    EUR267 to EUR300/night

  13. HOUSE
    Villa Stefano

    Villa Stefano

    Buseto Palizzolo, TP

    Charming house with private pool in a beautiful area Villa Rita is a charming house in Buseto Palizzolo. It is located in a privileged panoramic view over the city of Trapani, the Egadi Islands, Erice and Valderice. It is about one km from the...

    Pool

    EUR267 to EUR447/night

  14. VILLA
    Villa Isa

    Villa Isa

    Montefelcino, PU

    Villa with a private swimming pool at a panoramic location with views of the sea This beautiful villa is located in the hills close to the beautiful beaches of the coastal towns of Fano and Pesaro. The villa is situated in the hills and offers a lot...

    Pool

    EUR266 to EUR559/night

  15. CHALET
    Ibiscus

    Ibiscus

    Gratillon Saint Nicolas, AO

    Magnificent apartment with private sauna in a historic village near Aosta Beautiful apartment in a chalet located in a historic village a few kilometers from Aosta.Spacious,elegant and refined. Furnished with style and care of every detail.Charming...

    EUR266 to EUR280/night

  16. HOUSE
    Casa Pizziddu

    Casa Pizziddu

    Acireale, CT

    Attractive sunny and cosy holiday home at the beautiful, clear, Sicilian Sea This attractive, sunny holiday home is beside the clear, azure Sicilian Sea. The spacious terrace (100m2) is perfect for enjoying delightful evenings. You can admire...

  17. CHALET
    Lotus

    Lotus

    Gratillon Saint Nicolas, AO

    Magnificent apartment with Zen garden in a historic village near Aosta Beautiful apartment in a chalet located in a historic village a few kilometers from Aosta.Elegant and refined. Furnished with style and care of every detail.Charming and elite...

    EUR266 to EUR280/night

  18. VILLA
    Otto a Loro Ciuffenna

    Otto a Loro Ciuffenna

    Loro Ciuffenna, AR

    Situated in the Tuscany hills between Arezzo and Florence. Spacious and lovely villa panoramically situated in the Tuscany hills, between Arezzo and Florence. The house ( on 2 levels) offers all the comfort and among others a private swimming pool,...

    Pool

    EUR265 to EUR394/night

  19. VILLA
    Villa Pierina

    Villa Pierina

    Cortona, AR

    Villa with private pool, 3 km from Cortona, 3 apartments Villa Pierina is a beautiful property near Cortona, whose view of the gentle slopes and monuments creates an unmistakable skyline, visible from the garden of the villa, creating a unique...

    Pool

    EUR265 to EUR654/night

  20. COTTAGE
    Trulli Margherita

    Trulli Margherita

    Monopoli, BA

    Trulli in the countryside with private pool between the fruit and olive trees This lovely group of Puglia Trulli (traditional limestone dwellings) with private pool is situated in a hilly region, just a few miles away from the crystal-clear waters...

    Pool

    EUR265 to EUR398/night

  21. HOUSE
    Villa del Duca

    Villa del Duca

    Civitella San Paolo, RM

    Villa with swimming pool in Fiano Romano, ideal for a Roman holiday The Villa is situated in the green Roman countryside and enjoys an excellent panoramic position. It faces a valley from where you can see Mount Soratte and in the evenings you can...

    Pool

    EUR264 to EUR479/night

  22. HOUSE
    Casale Liana

    Casale Liana

    Castiglione di Garfagnana, LU

    A nice rural house surrounded by hills and fields Casa Liana is a beautiful rural house, surrounded by the fields and hills of Tuscany. The apartment is on the ground floor. It has a spacious garden with plenty of privacy. The owner has carefully...

    EUR264 to EUR412/night

  23. VILLA
    Villa Max

    Villa Max

    Suvereto, LI

    House with private pool, pizza oven, BBQ, ping pong, jacuzzi, just call it! This very comfortable holiday home with private pool features a large garden with different seating areas. In addition to various shady terraces, the garden also offers many...

    Pool

    EUR264 to EUR494/night

  24. ESTATE
    Residence Templari Uno 6P

    Residence Templari Uno 6P

    Montebello Vicentino, VI

    Captivating and historic restored home, with ample garden, privacy Historic building dating back to the 17th century, finely restored and offering guests all necessary comforts. The property benefits from large and well cared-for outdoor spaces and...

    EUR264 to EUR280/night

  25. VILLA
    Villa San Lorenzo La Siesta

    Villa San Lorenzo La Siesta

    Treia - Macerata, MC

    Charming villa from the 16th century with private pool and large garden in the beautiful nature This superb villa with a large garden stems from the 16th century and has been completely restored. From the garden you have a panoramic view of the...

    Pool

    EUR262 to EUR493/night

  26. VILLA
    Villa Caracciole

    Villa Caracciole

    Fossombrone, PU

    Villa with private pool, stunning views, near sea Villa Caracciole is a cozy and carefully restored villa located in the Metauro valley near Fossombrone. The villa is situated in a panoramic position with a beautiful view over the valley with hills,...

    Pool

    EUR260 to EUR492/night

  27. VILLA
    Villa Sole

    Villa Sole

    Anghiari, AR

    A villa in the Tiber valley with a private swimming pool. Villa Sole is surrounded by the beautiful landscape of the Tiber Valley. It has a private swimming pool. The spacious villa nestles between the Rivers Tiber and Arno. It is simply full of...

    Pool

    EUR260 to EUR511/night

  28. APARTMENT
    Chianti Village Morrocco T5

    Chianti Village Morrocco T5

    Tavarnelle val di Pesa, FI

    Comfortable apartment with airconditioning and enclosed pool in Chianti Enjoy! This apartment is fresh, comfortable, and neatly furnished, and is equipped with air conditioning. It's part of a spacious holiday park with several facilities. First,...

    Pool

    EUR260 to EUR334/night

  29. VILLA
    Villa Rapolano

    Villa Rapolano

    Armaiolo, SI

    Beautiful villa with private garden and private pool, two terraces and wifi Rapolano villa with private garden and swimming pool is an ideal place to spend your holidays with family and friends. The villa is in the area of Siena on the border of...

    Pool

    EUR260 to EUR429/night

  30. VILLA
    Villa Tortelli

    Villa Tortelli

    San Romano di Garfagnana, LU

    Holiday villa with private pool, Jacuzzi, large garden in the Tuscan hills With this luxury villa, you can start relaxing immediately! Take a refreshing dip in your own swimming pool with Jacuzzi and outdoor shower. Afterwards you can have a stroll...

    Pool

    EUR260 to EUR508/night