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 Mimmo

    Villa Mimmo

    Cortona, AR

    Villa Mimmo lies on the border of Tuscany and Umbria, near the ancient Etruscan city of Cortona. The villa is located in a hilly area with forests, olive trees and vineyards interspersed with small medieval villages. From the hills, you'll overlook...

    Pool Pets OK

    $400 to $600/night

  2. HOUSE
    Villa San Donato

    Villa San Donato

    Umbertide, PG

    Get to know this beautiful villa! Your vacation address is surrounded by a large, fenced off yard of 3 ha. and a beautiful olive orchard. In front of the villa is a large private swimming pool. Take a refreshing dive and admire the phenomenal view....

    Pool Pets OK

    $399 to $753/night

  3. HOUSE
    Il Giglio 12

    Il Giglio 12

    Montefiascone, VT

    Villa il Giglio is situated on top of a green hill with a lovely view over Lake Bolsena and the valleys and surrounding hills of Tuscia, in Tuscany and Umbria, a short distance from Montefiascone town. The villa has been recently restored and...

    Pool

    $396 to $716/night

  4. HOUSE
    Casale Staiano

    Casale Staiano

    Massa Lubrense, NA

    The house is a countryside farmhouse with plenty of charm and character. It lies just outside the popular small town of Sant’Agata sui due Golfi.   
 The farmhouse is surrounded by lovely communal gardens, filled with olive trees and pots of...

    $396 to $1692/night

  5. HOUSE
    Trulli la Cedrina

    Trulli la Cedrina

    Ceglie Messapica, BR

    The trulli is a luxurious holiday home in Puglia which has been carefully restored in authentic Apulian style. This luxury villa has a private infinity swimming pool with a 'beach effect' and accommodates up to 8 guests. One of the main highlights...

    Pool

    $395 to $813/night

  6. HOUSE
    Villa Lecceta

    Villa Lecceta

    Rignano Sull'arno, FI

    Lovely and spacious house (350 m2, ground fl. and 1st floor), in the region of Florence, typical Tuscan furniture and recently renovated. Situated on a big estate, which belongs to a monumental and historic "Villa", where there are other cottages as...

    Pool Pets OK

    $395 to $504/night

  7. HOUSE
    Villa Trecastagni

    Villa Trecastagni

    Viagrande, CT

    This luxury detached villa is located in a quiet residential area and is beautifully furnished. The modern bathroom and full kitchen make the house complete with all the modern conveniences. The large enclosed garden with diverse fruit trees provide...

    Pool

    $393 to $953/night

  8. HOUSE
    Villa Ulivo e Edera

    Villa Ulivo e Edera

    Radda in Chianti, SI

    This old Tuscan farmhouse has been completely restored and is near Radda in Chianti in Chianti Classico. The farm consists of 3 apartments and a few rooms. The decor is rustic and typically Tuscan with wooden beams on the ceiling. The farm is...

    Pool Pets OK

    $392 to $617/night

  9. HOUSE
    Casanova

    Casanova

    San Pancrazio, FI

    Set in the Florentine Chianti countryside, Podere Casanova occupies a beautiful panoramic position. It is surrounded by private gardens and features a large pool. It can be easily reached by all major Tuscan road and rail networks. It is just 25 km...

    Pool Pets OK

    $390 to $580/night

  10. HOUSE
    Di Vinci

    Di Vinci

    Vinci - Florence, FI

    In the birthplace of Leonardo da Vinci, located a few kilometers from Florence, you will find this typical Tuscan stone farmhouse, whose origins date back to 1500. Restored by the owners with great care and maintaining the authenticity of the place,...

    Pool Pets OK

    $389 to $621/night

  11. HOUSE
    Villa Fiorentino

    Villa Fiorentino

    Castiglion Fiorentino, AR

    This cozy and beautiful agriturismo is in Castiglione Fiorentino in the rolling hills with forests, vineyards and olive trees. There are a total of three apartments overlooking a spacious garden. Two apartments are adjacent and the third apartment...

    Pool Pets OK

    $389 to $575/night

  12. HOUSE
    Gatterino

    Gatterino

    Peccioli, PI

    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. Peccioli has all the characteristics Toscane is famous...

    Pool

    $386 to $587/night

  13. HOUSE
    Borgo Gallinaio Glicine

    Borgo Gallinaio Glicine

    Camaiore, LU

    This very charming and beautifully finished apartment has been lovingly decorated, and it shows. The house is located on a lovely and spaciously laid out domain of 3 ha. The grounds are home to a total of 8 holiday homes and apartments. The...

    Pool Pets OK

    $385 to $511/night

  14. HOUSE
    Villa Azzurrina

    Villa Azzurrina

    Serrapetrona, MC

    Villa Azzurrina is a typical villa with pool in Serrapetrona, a small hamlet near Macerata. The villa is within walking distance of restaurants and shops and in the morning you can drink a delicious cappuccino after a short walk. The villa has a...

    Pool Pets OK

    $385 to $547/night

  15. HOUSE
    Villa Casetta

    Villa Casetta

    Sonnino, LT

    Villa Casetta is a cozy and comfortable villa near Sonnino, in the southern part of the Lazio region. The fully fenced villa is situated in a very quiet location with lots of privacy. The villa is in the countryside and you have a beautiful view...

    Pool Pets OK

    $383 to $618/night

  16. HOUSE
    Villa Silva

    Villa Silva

    Cortona, AR

    Villa Silvia is a typical Tuscan rustic house in the idyllic hills north of the Etruscan city of Cortona. The center of Cortona is only 1.5 km away and is near the famous Santa Maria Nuova church. The rustic-style villa has old terracotta floors,...

    Pool Pets OK

    $383 to $566/night

  17. HOUSE
    Villa Angela

    Villa Angela

    Montereale di Cesena, FC

    Villa Angela is a beautiful spacious villa which can be hired by floor or as a whole. There is a beautiful living room with an open fireplace on both floors. The villa is at the top of a hill 360 metres above sea level only 10 minutes from the town...

    $381 to $436/night

  18. HOUSE
    Mulino delle Fontanacce

    Mulino delle Fontanacce

    Montecatini Val di Cecina, PI

    Characteristic mill water produced by the Count Ugolino della Gherardesca in 1829 and made habitable in years" 50 while maintaining the original architectural features. Located in the hinterland of the Tuscan coast in the town of Montecatini Val di...

    Pool Pets OK

    $380 to $594/night

  19. HOUSE
    Vecchia Dimora Resort

    Vecchia Dimora Resort

    Centuripe, EN

    The villa is a historic building which was recently renovated, and it belongs to an organic farmi that is still fully active. It therefore has kept its rural character, not to mention the background to the incredibly beautiful countryside around and...

    Pool Pets OK

    $379 to $639/night

  20. HOUSE
    Villa Spaziosa

    Villa Spaziosa

    Valderice, TP

    Villa Spaziosa is a fantastic place to spend your well-deserved holiday. The villa is located inside a natural pine forest, in a valley, as a result there is so much green, the area is very quiet and you will enjoy total privacy. It lies in the...

    Pool

    $377 to $596/night

  21. HOUSE
    Villa Simona

    Villa Simona

    Meina, NO

    This exclusive villa is situated directly at the shores of the Lake Maggiore. It has a private swimming pool and its own small beach. The modern villa is all on one level. It looks out on Lake Maggiore and is very near the village of Meina. The home...

    Pool Pets OK

    $377 to $435/night

  22. HOUSE
    Gisella Paterno

    Gisella Paterno

    Chianni, PI

    Old farmhouse renovated with taste and harmoniously incorporated in the splendid green hills of Pisa. In an oasis of tranquility, in a privileged position for its exposure. The property comprises large living room with fireplace, reading area...

    Pool Pets OK

    $375 to $586/night

  23. HOUSE
    Lauras

    Lauras

    Marsala, TP

    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 spacious, well kept interior spaces and outdoor areas. On the ground floor...

    Pool

    $372 to $772/night

  24. HOUSE
    Villa Manziana

    Villa Manziana

    Manziana, RM

    This beautiful, stylish detached villa is part of a country estate. The estate is on a hill and offers wonderful views of the area. The fine furniture reflects the superb style of the villa. The villa is next to the main building of the estate, near...

    Pool

    $371 to $510/night

  25. HOUSE
    Santo Vento

    Santo Vento

    San Fratello, ME

    The family had the dream to revive their old houses from 1820. They built this farm at the foot of the mountain, an oasis of calm and relaxation. It is situated on the edge of the beautiful Nebrodi Park at an altitude of 450 m, the sea is only 10...

    Pool

    $368 to $557/night

  26. HOUSE
    Casa Relax nel Verde

    Casa Relax nel Verde

    Pisogne, BS

    nullExtra CostsDeposit: € 200Pets: Max. 2; € 25/Pet/StayBed linen: Possible to rent per package, € 10 p.p./StayOptional services on siteBath towels: Included in the price when you rent a linen packageWifi: FreeCot: free (on...

    Pool Pets OK

    $368 to $757/night

  27. HOUSE
    Villa Verde

    Villa Verde

    Cortona, AR

    Villa Verde is a rustic farmhouse about 400 meters above sea level in the hills near Cortona. The villa is surrounded by rolling hills and offers privacy and tranquility. Thanks to a careful restoration, this old country house from the seventeenth...

    Pool Pets OK

    $363 to $706/night

  28. HOUSE
    Villa a Loro Ciuffenna

    Villa a Loro Ciuffenna

    Loro Ciuffenna, AR

    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, garden, garage. Not only the accomodation, but also the...

    Pool Pets OK

    $362 to $731/night

  29. HOUSE
    Pignabianca

    Pignabianca

    Marusa, TP

    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 overlooks its lovely garden, offers - besides the swimming pool - large, panoramic...

    Pool

    $360 to $700/night

  30. HOUSE
    Villa Isolina

    Villa Isolina

    Cortona, AR

    In the heart of Tuscany's most authentic Tuscan countryside, Villa Isolina is an ancient farmhouse completely restored in colonial stone, keeping the traditional rural style intact. The interiors are rustic Tuscan style, the ceiling with exposed...

    Pool Pets OK

    $359 to $638/night