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. VILLA
    Villa Torre

    Villa Torre

    Pietranico, PE

    Villa with tower between olive trees with private swimming pool, nice view 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...

    Pool

    EUR440 to EUR713/night

  2. HOUSE
    Villa Mezzogiorno

    Villa Mezzogiorno

    Cortona, AR

    Magnificent villa, extremely panoramic position, sauna, jacuzzi and private pool Villa Mezzogiorno is the perfect place for an unforgettable experience! This magnificent property is situated in the heart of the hills of Cortona, in an extremely...

    Pool

    EUR437 to EUR727/night

  3. HOUSE
    Villa Bottoni

    Villa Bottoni

    Ripabottoni, CB

    House with pool, garden and wifi in medieval village, with panoramic views. 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...

    Pool
  4. HOUSE
    Villa Oliva

    Villa Oliva

    Ghizzano Peccioli, PI

    Workers' land on estate with pool near Pisa and Florence. 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...

    Pool

    EUR435 to EUR621/night

  5. VILLA
    Casale Offida

    Casale Offida

    Offida, AP

    Villa with private swimming pool, near the Riviera delle Palme, hilly area 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...

    Pool

    EUR434 to EUR647/night

  6. VILLA
    Villa Nella

    Villa Nella

    Cortona, AR

    Typical Tuscan farmhouse with private swimming pool, 900m away from a small bar 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...

    Pool

    EUR434 to EUR543/night

  7. VILLA
    Villa Allegra

    Villa Allegra

    Allerona, TR

    Luxury villa with private pool and beautiful decor and trendy portico 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...

    Pool

    EUR430 to EUR683/night

  8. VILLA
    Spiga

    Spiga

    Noto, SR

    Ancient countryside residence with pool, in the heart of the Baroque Sicily. 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...

    Pool

    EUR428 to EUR644/night

  9. 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

  10. ESTATE
    La Contea

    La Contea

    Rosello, CH

    Spacious, luxury apartment in Castle Giuliopoli with Pool 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...

    Pool

    EUR425 to EUR467/night

  11. VILLA
    Villa White

    Villa White

    San Feliciano, PG

    Elegant and modern villa in the hills, with private swimming pool and view over the lake 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...

    Pool

    EUR422 to EUR673/night

  12. VILLA
    Avane

    Avane

    Pian di Sco' (arezzo), AR

    Luxury villa with pool and lots of privacy near Florence and Arezzo This luxury villa at 560 meters hight, with a fantastic view is situated at the edge of the Chianti and at the foot of the Apennines, the ideal point of departure for enjoyable...

    Pool

    EUR422 to EUR911/night

  13. VILLA
    Gualtierotti

    Gualtierotti

    Pistoia, PT

    Exclusive villa in the countryside of Pistoia with private pool and jacuzzi 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...

    Pool

    EUR421 to EUR916/night

  14. VILLA
    Villa Celeste

    Villa Celeste

    Cortona, AR

    Villa with spacious garden and private pool, barbecue and pizza oven, near Cortona Villa Celeste is situated in open countryside between Cortona and Lake Trasimeno. The villa has a large garden with roses and other plants and is surrounded by green...

    Pool

    EUR421 to EUR645/night

  15. VILLA
    Villa Isabella

    Villa Isabella

    Cortona, AR

    Charming villa in idyllic surroundings, with private swimming pool and spacious garden 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...

    Pool

    EUR420 to EUR816/night

  16. FARMHOUSE
    Acquaviva Intero

    Acquaviva Intero

    Montescudaio, PI

    Typical Tuscan farmhouse, surrounded by vineyards 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...

    Pool

    EUR417 to EUR1,210/night

  17. VILLA
    Villa Passignano

    Villa Passignano

    Passignano sul Trasimeno, PG

    Luxurious villa with private pool and panoramic views over Lake Trasimeno 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,...

    Pool

    EUR417 to EUR706/night

  18. VILLA
    Villa Tuoro

    Villa Tuoro

    Tuoro sul Trasimeno, PG

    Villa with pool and garden, beautiful view over Lake Trasimeno 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...

    Pool

    EUR416 to EUR981/night

  19. HOUSE
    Villa Beatrice

    Villa Beatrice

    Assisi, PG

    Villa with private garden and swimming pool in town centre, near bar and restaurant 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...

    Pool

    EUR416 to EUR570/night

  20. VILLA
    Villa Graziosa

    Villa Graziosa

    Cortona, AR

    Villa with private swimming pool and spacious garden in the Valdichiana, close to Cortona 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...

    Pool

    EUR416 to EUR771/night

  21. VILLA
    Villa Acropolis 17

    Villa Acropolis 17

    Anzio, RM

    Spacious villa with pool and jacuzzi in the countryside of Anzio 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...

    Pool

    EUR412 to EUR707/night

  22. FARMHOUSE
    Villa Ulivo e Edera

    Villa Ulivo e Edera

    Radda in Chianti, SI

    Farmhouse with pool, terrace and garden, walking distance from Radda in Chianti 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...

    Pool

    EUR410 to EUR558/night

  23. HOUSE
    Casasellate

    Casasellate

    Volterra, PI

    Your own piece of Tuscany in an oasis of calm with a lovely private pool 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,...

    Pool

    EUR409 to EUR747/night

  24. VILLA
    Vanzetto

    Vanzetto

    Tredozio, FC

    Villa with swimming pool and panoramic view of the Apennines This beautiful villa has two individual apartments, which can be hired as a whole, which makes this villa ideal for a family or group of friends who want to enjoy the peace in an apartment...

    Pool

    EUR408 to EUR668/night

  25. HOUSE
    Il Casolare di Valle

    Il Casolare di Valle

    Anghiari, AR

    Beautiful accommodation in elegant farmhouse with pool and breathtaking views Stay in a delightful holiday home at the Valle di Mezzo: a traditional stone farmhouse immersed in nature, where guests will enjoy a haven of peace and tranquillity....

    Pool

    EUR408 to EUR550/night

  26. APARTMENT
    Dei Medici

    Dei Medici

    Florence, FI

    Beautiful apartment in the center of Florence 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...

  27. VILLA
    Arangea

    Arangea

    Marsala, TP

    Beautiful villa with pool situated near Marsala, town by the sea 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...

    Pool

    EUR407 to EUR812/night

  28. VILLA
    Villa Magnifico

    Villa Magnifico

    Castiglion Fiorentino, AR

    Villa with private swimming pool in stunning location with breathtaking views 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...

    Pool

    EUR404 to EUR500/night

  29. HOUSE
    Villa Giunone

    Villa Giunone

    Ghizzano Peccioli, PI

    Beautiful detached villa on beautiful Tuscan estate This beautiful villa with private pool lies on a century-old estate where, among others, grapes and grain are still being biologically grown. This stunning, hilly piece of land is a beautiful part...

    Pool

    EUR397 to EUR630/night

  30. VILLA
    Villa Vista

    Villa Vista

    Castiglion Fiorentino, AR

    Villa with private swimming pool and garden, panoramic view over the valley Villa Vista is located in the hills at about 600 meters altitude, between the historic cities of Cortona and Castiglion Fiorentino, It is a fully independent villa with...

    Pool

    EUR397 to EUR608/night