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.

Filter by Region:


Filter by Amenities:


Filter by Entertainment:


Close Filters
  1. FARMHOUSE
    Gli Archi

    Gli Archi

    Cortona, AR

    Farmhouse with private terrace, garden and pool, overlooking the town of Cortona A characteristic agritourism 3 km away from the special Etruscan city of Cortona. Near the town, yet surrounded by countryside in the Chiana valley, among olive groves...

    Pool

    EUR66 to EUR138/night

  2. HOUSE
    Podere Rigo Suite

    Podere Rigo Suite

    Celle sul Rigo, SI

    Comfortable apartment with stunning views, near hot springs This comfortable apartment is one of three in a fully renovated farmhouse. Located at 600 meters altitude, the house offers breathtaking views. But not only from the house; thanks to the...

    Pool

    EUR86 to EUR109/night

  3. VILLA
    Villa Marcy

    Villa Marcy

    Marciano Della Chiana, AR

    Villa with private pool, beautiful view, in the Chiana Valley, wifi 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...

    Pool

    EUR486 to EUR970/night

  4. HOUSE
    Villa Il Cedro

    Villa Il Cedro

    Cortona, AR

    Beautiful restored villa with private swimming pool in the Tuscan countryside A few steps from the beautiful Etruscan town of Cortona, rises Il Cedro, a beautiful stone building recently restored, set in a strategic position from which you can enjoy...

    Pool

    EUR472 to EUR845/night

  5. VILLA
    Villa Ruby

    Villa Ruby

    Lisciano Niccone, PG

    Villa with private swimming pool, in the hills near lake Trasimeno Among the beautiful plain of Lake Trasimeno and the luxuriant Umbrian hills stands Villa Ruby, an ideal destination for those looking to stay in a landscape of rare beauty,...

    Pool

    EUR397 to EUR595/night

  6. 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

  7. VILLA
    Villa Quirico

    Villa Quirico

    Serra san Quirico, AN

    Villa with private pool, rural and charming, 30 minutes from the sea Villa Quirico is situated in the hills near Serra San Quirico, just 30 minutes from the Adriatic coast. The decor is cozy and rustic. The villa is a cozy and renovated farmhouse...

    Pool

    EUR324 to EUR596/night

  8. 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

  9. HOUSE
    Podere Vallerona La Caciaia

    Podere Vallerona La Caciaia

    Arcidosso, GR

    Attractive apartment with large pool and jacuzzi in a beautiful setting The history of the farmhouse has very remote origins, and we find it in documents of the 13th century, where it is described as a place of worship built by monks dedicated to...

    Pool

    EUR78 to EUR118/night

  10. HOUSE
    La Viola

    La Viola

    Popiglio, PT

    A beautiful nature corner of Tuscany to disconnect from the daily stress An unspoiled area of Tuscany to help you take a break from the daily grind. We think we've got what you need; air and pure water; tranquillity, lake excursions; horse rides,...

    Pool

    EUR110 to EUR147/night

  11. ESTATE
    Le Muse REQ

    Le Muse REQ

    Lucca, LU

    In a sunny and scenic position on the hills of Lucca Beautiful apartment in the historic center of Lucca situated on the 1st floor with a large terrace of 40 sqm, very bright and friendly furnished in a modern style, ideal location to visit the city...

    EUR202 to EUR229/night

  12. HOUSE
    Masseria Tarsia Incuria

    Masseria Tarsia Incuria

    Conversano, BA

    A luxurious and spacious Masseria with private pool on 1 hectare of private land 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...

    Pool

    EUR461 to EUR963/night

  13. HOUSE
    Morgana

    Morgana

    Donnalucata, RG

    Comfortable apartment in a villa in Donnalucata just 20m from the sea Comfortable beach villa divided into three independent apartments situated a few kilometres away from the characteristic fishing village of Donnalucata. Overlooking a delightful...

    EUR213 to EUR300/night

  14. HOUSE
    Colombaia

    Colombaia

    Spoleto, PG

    Historic and charming estate with swimming pool and restaurant in the hills This beautiful historic estate dating from the fifteenth century is situated in the hills near the town of Poreta halfway between Spoleto and Trevi. The estate is one of the...

    Pool

    EUR200 to EUR427/night

  15. APARTMENT
    Casa Francesca

    Casa Francesca

    Roma, RM

    Large apartment central and strategic position perfect to visit Rome This pretty and spacious apartment has a basic, but attractive interior. It's a perfect base for families who want to visit Rome. You'll have everything within reach, the bus stop...

    EUR184 to EUR208/night

  16. HOUSE
    Le Scalette

    Le Scalette

    Ronta, FI

    Apartment in a nice little village at 500 meters, not far from Florence This agriturismo is a cute small rural village at about 500 meters altitude and not far from Florence, surrounded by olive groves and vast chestnut forests. The four apartments...

    Pool

    EUR131 to EUR199/night

  17. ESTATE
    Il Grano

    Il Grano

    Apecchio, PU

    Property with swimming pool, spacious garden, private terrace and views On the border between Umbria and Le Marche is a beautiful estate in the Candigliano Valley, between the towns of Piobbico, Apecchio, Urbania and Sant'Angelo in Vado. The...

    Pool

    EUR71 to EUR124/night

  18. ESTATE
    Casa dei Nonni

    Casa dei Nonni

    Provaglio d'Iseo, BS

    Ancient, renovated farmstead with private, equipped garden. Only 3km from the lake. The accommodation is part of an ancient farmstead which, together with other units, used to be the first local inhabited settlement, established around a monastery...

    EUR89 to EUR128/night

  19. VILLA
    Casa Magnano Ziano

    Casa Magnano Ziano

    Ziano, PC

    A villa on a hill, surrounded by vineyards, with a splendid 360° view. A secluded villa on a hill, surrounded by vineyards, with a splendid 360° view. The ideal place to relax and get away from everyday’s hectic, with nature as your only...

    EUR130 to EUR197/night

  20. FARMHOUSE
    Orchidea

    Orchidea

    Castiglion Fiorentino, AR

    Farmhouse with garden, private terrace, panoramic swimming pool, organic wine 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...

    Pool

    EUR103 to EUR136/night

  21. FARMHOUSE
    Ginepro

    Ginepro

    Montalto di Castro, VT

    Located on the ground floor, this refined apartment .... Located on the ground floor, this refined apartment is extremely luminous thanks to its light coloured furnishings. Included In Price Final Cleaning Bed linen Bath towels Kitchen linen...

    Pool

    EUR132 to EUR197/night

  22. COTTAGE
    Giardino

    Giardino

    Civitella Paganico, GR

    Holiday home with pool in a former church in the Tuscan hills Giardino is an apartment in a former church, built in the year 1000 with an entrance on the side. At the front of church is a large space that is used for special activities such as a...

    Pool

    EUR220 to EUR286/night

  23. APARTMENT
    Mda per Due

    Mda per Due

    Matera, MT

    Spacious apartment with parking and WiFi within walking distance of the centre. This House is spacious and modern and is located on the third floor of a new building with elevator. The house is only five minutes on foot from Via D'Addozio which is...

    EUR111 to EUR143/night

  24. VILLA
    Casa de Poi

    Casa de Poi

    Salsomaggiore Terme, PR

    Magnificent old country house with garden and private pool, with Wifi 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...

    Pool

    EUR425 to EUR962/night

  25. 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

  26. HOUSE
    Turiello

    Turiello

    Termini, NA

    Lovely apartment on a panoramic position with lots of nice garden corners The apartment is located in a beautiful position in the countryside, just ten minutes drive from the centre of Sorrento. Perched on a hillside, it offers stunning views...

    EUR223 to EUR444/night

  27. COTTAGE
    Montesorano

    Montesorano

    Sorano, GR

    Lovely house in the Maremma, private terrace and views A beautiful holiday in the Maremma region of Tuscany. The house is only 1 km away from the Therme of Sorano and nearby Lake Bolsena. There are 3 apartments with a private terrace where you can...

    EUR52 to EUR92/night

  28. HOUSE
    La Cumbre

    La Cumbre

    Lucca, LU

    Charming and comfortable villa near Lucca with private pool Since three generations the family owns this charming 18th century farm house on the hills of the medieval city of Lucca, just beside an 11th century small white stoned facade church. The...

    Pool

    EUR457 to EUR716/night

  29. HOUSE
    Borgo Gallinaio Fico

    Borgo Gallinaio Fico

    Camaiore, LU

    Cozy and beautifully decorated house in the Tuscan hills with private pool This beautifully finished and atmospheric holiday home has been decorated with love. The house is located on a lovely and spaciously laid out domain of 3 ha. The grounds are...

    Pool

    EUR199 to EUR265/night

  30. FARMHOUSE
    Sorano

    Sorano

    Sorano, GR

    Apartment in an organic farm with sheep, pool, quiet location An organic farm in the green Tuscany with 110 hectares of land with wheat fields, olive groves, vineyards and sheep from Sardinia. The home-produced olive oil and wine is sold in the...

    Pool

    EUR90 to EUR170/night