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. CONDOMINIUM
    La Peninsula Home #40385

    La Peninsula Home #40385

    Naples, FL

    Incredible views of the from this 3rd floor spacious 2 bedroom 2 1/2 bath condo! 2140 Sq Ft. Amenities include tennis courts on site, fitness center, heated pool and spa, docks for fishing. AmenitiesElevatorSightseeingBalconyFamilyOutdoor...

    Pool

    $126 to $230/night

  2. HOUSE
    Castagneto 7

    Castagneto 7

    Castagneto Carducci, LI

    Magnificent apartment located on the private beach of Marina di Castagneto Carducci This beautiful apartment is located in a modern four-storey building, right on the beach of Marina di Castagneto Carducci. You reach this tastefully decorated...

    EUR125 to EUR312/night

  3. HOUSE
    Sassetta 2

    Sassetta 2

    Sassetta, LI

    Detached house with pool 12 km from the private beach This beautiful detached holiday home with shared pool is situated in a hilly area near Sassetta, at an altitude of 500 meters. The holiday home is tastefully decorated and fully equipped. In...

    Pool

    EUR176 to EUR369/night

  4. FARMHOUSE
    La Villa

    La Villa

    Rufina, FI

    Spacious apartment in the wing of a wine estate in Tuscany You'll be staying in a spacious apartment in the wing of a winery. It's a great house for people who like an authentic atmosphere. The two bedrooms have antique beds. The rooms are spacious...

    Pool

    EUR135 to EUR155/night

  5. HOUSE
    Castagneto 4

    Castagneto 4

    Castagneto Carducci, LI

    Nice apartment in a wooded area 300 meters from the private beach This lovely apartment is situated in a sixties villa in a wooded area, just 300 meters from the beach of Marina Castagneto Carducci. The apartment is on the ground floor and is...

    EUR87 to EUR236/night

  6. COTTAGE
    Casa Arena

    Casa Arena

    Pescaglia, LU

    Stone house, immersed in nature with fenced garden and private pool Beautiful house partially built in stone, immersed in nature with an enclosed garden, private swimming pool (above-ground 6.60 x 2.80m, 1m deep), a perfect choice for those who love...

    Pool

    EUR131 to EUR173/night

  7. 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...

    EUR410/night

  8. VILLA
    Fontana Tutto

    Fontana Tutto

    Monteverdi Marittimo, PI

    Luxury air conditioned villa with private pool on large grounds with terrace You are bound to enjoy yourself in this pleasant, spacious villa situated up in the hills by Monteverdi Marittimo. Enjoy the enclosed private swimming pool with outdoor...

    Pool

    EUR310 to EUR378/night

  9. HOUSE
    Agriturismo Foiano Tabaccaia

    Agriturismo Foiano Tabaccaia

    Castiglion Fiorentino, AR

    Nice and cozy apartment in a natural environment near the Chianti Valley This pleasant apartment is part of a beautiful agriturismo with a total of 8 apartments and 1 detached house. The apartment has authentic and cosy furnishings. Together with...

    Pool

    EUR112 to EUR204/night

  10. VILLA
    Fontana Sei

    Fontana Sei

    Monteverdi Marittimo, PI

    Luxury air conditioned villa with private pool on large grounds with terrace You are bound to enjoy yourself in this pleasant, spacious villa situated up in the hills by Monteverdi Marittimo. Enjoy the enclosed private swimming pool with outdoor...

    Pool

    EUR167 to EUR212/night

  11. BUNGALOW
    Sogni d'Acqua

    Sogni d'Acqua

    Casalborsetti, RA

    Bungalow with swimming pool at only 200mt from the sea. The bungalow is located in Casalborsetti, at the north shore of the Ravenna Riviera and is about 15 minutes from the historic Ravenna and the famous park Mirabilandia. At a short distance you...

    Pool

    EUR90 to EUR173/night

  12. HOUSE
    Appartamento Giaggiolo

    Appartamento Giaggiolo

    Stabbia, FI

    Perfectly rural location, apartment with swimming pool. This apartment is part of a farmhouse in the heart of Tuscany. It is a family business in a strategic location for visiting Tuscany's most important cities without having to sacrifice a...

    Pool

    EUR76 to EUR203/night

  13. HOUSE
    Villa Mimmo

    Villa Mimmo

    Cortona, AR

    Villa with private swimming pool and bowling alley, hilly area 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...

    Pool

    EUR366 to EUR548/night

  14. FARMHOUSE
    Mimosa

    Mimosa

    Montepulciano, SI

    Farmhouse with swimming pool, overlooking vineyard Vino Nobile di Montepulciano Near the medieval town of Montepulciano is a beautiful winery with eight apartments and a swimming pool. The agriturismo is located in the rolling hills of grain fields...

    Pool

    EUR122 to EUR171/night

  15. HOUSE
    Corbezzolo

    Corbezzolo

    San Giovanni Valdarno, AR

    Beautiful maintained apartment on large estate in the middle of the beautiful Chianti region This nice and neatly kept apartment is on a large estate. In total there are 4 apartments divided over 2 buildings. You and the other residents have access...

    Pool

    EUR125 to EUR233/night

  16. HOUSE
    Podere San Donato Due

    Podere San Donato Due

    San Donato in Fronzano (fi), FI

    Attractive apartment on estate with vineyards and olive grove, near Florence This cozy apartment is part of a large 18 acre estate. This property houses a number of restored buildings that are home to a total of 6 apartments. The apartment is...

    Pool

    EUR98 to EUR144/night

  17. HOUSE
    Sassetta 3

    Sassetta 3

    Sassetta, LI

    Nice apartment in the Tuscan hills, 12 km from the private beach This beautiful apartment with shared pool is situated in a sixties villa in a hilly area near Sassetta, at an altitude of 500 meters. There are three apartments in the villa. This...

    Pool

    EUR82 to EUR175/night

  18. FARMHOUSE
    Vasari

    Vasari

    Dicomano (fi), FI

    Attractive apartment in vineyard with swimming pool and views over Tuscany This complex, which still produces its own wine and olive oil, is a perfect base for exploring the Tuscany region. On top of a hill is a group of 7 beautifully restored...

    Pool

    EUR90 to EUR232/night

  19. CHALET
    Chalet 4 plus 1

    Chalet 4 plus 1

    Lido di Dante, RA

    Chalet in the middle of nature at only 200mt from the beach The chalet is located in Lido di Dante, a seaside resort of the Adriatic coast about 6 Km from the city of Ravenna and 8 km from the amusement park of Mirabilandia. The chalet is...

    Pool

    EUR105 to EUR134/night

  20. FARMHOUSE
    Portico

    Portico

    Montepulciano, SI

    Farm holiday with swimming pool, 500 m from Montepulciano, beautiful surroundings Portico is a charming apartment in an agritourism area. This old stone farmhouse has been completely renovated and there are 4 apartments in total. The agritourism...

    Pool

    EUR100 to EUR136/night

  21. FARMHOUSE
    Montecchio

    Montecchio

    Castiglion Fiorentino, AR

    Farmhouse with pool set among vineyards and olive trees, beautiful environment Apartment Montecchio is a beautiful apartment in an agriturismo. It is located in the valley of Roccavo dominated by the old castle of Montecchio. The agriturismo is...

    Pool

    EUR148 to EUR188/night

  22. COTTAGE
    Casa Lisa

    Casa Lisa

    Dicomano, FI

    Beautiful detached villa north of Florence Beautiful detached house north of Florence. These three small houses are located in the Tuscan countryside. The former farmhouse has been completely renovated. They are situated in a quiet area and are...

    Pool

    EUR97 to EUR199/night

  23. HOUSE
    Girasole

    Girasole

    Marina di Massa, MS

    Cozy appartment in Marina di Massa, just 500m from the sea and from the beach Apartment on the first and top floor of a lovely, peaceful building, with a very well-kept garden. As well as having a spacious lounge, it also has a furnished terrace...

    EUR93 to EUR256/night

  24. HOUSE
    Maison

    Maison

    Castelnuovo dei Sabbioni, AR

    Holiday home with shared swimming pool in the green hills of Chianti This charming house is part of a former farm house that produced wine, olive oil, fruit and vegetables. The complex consists of four free standing houses and two apartments. From...

    Pool

    EUR103 to EUR180/night

  25. HOUSE
    San Godenzo Sagrestia 2

    San Godenzo Sagrestia 2

    San Godenzo, FI

    Apartment in the historic medieval village of Serignana with pool and garden In the historic medieval borough of Serignana, placed at the edge of the Casentino National Park, you can find beautiful apartments perfectly suitable for your holidays in...

    Pool

    EUR92 to EUR204/night

  26. VILLA
    Villa Federica

    Villa Federica

    Cortona, AR

    Villa with private swimming pool in the Tuscan hills, only 1 km from Cortona A few steps from the beautiful Etruscan town of Cortona, which is only 1 km from the city center, lies Villa Federica, surrounded by orchards and crops, in a strategic...

    Pool

    EUR514 to EUR730/night

  27. 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

    EUR440 to EUR864/night

  28. FARMHOUSE
    Brunelleschi

    Brunelleschi

    Dicomano (fi), FI

    Attractive apartment in vineyard with swimming pool and views over Tuscany This complex, which still produces its own wine and olive oil, is a perfect base for exploring the Tuscany region. On top of a hill is a group of 7 beautifully restored...

    Pool

    EUR83 to EUR176/night

  29. COTTAGE
    Casale Castiglione

    Casale Castiglione

    Castiglione di Garfagnana, LU

    Cozy house with private pool and breathtaking views of the Garfagnana area The farmhouse is entirely handmade in stone and dates back to the late 1700. The structure faces South so you have the sun all for yourselves from 07.00 in the morning. You...

    Pool

    EUR219 to EUR334/night

  30. FARMHOUSE
    Fiore

    Fiore

    Montepulciano, SI

    Farm holiday with swimming pool, view over vineyard Vino Nobile di Montepulciano Near the medieval town of Montepulciano is a beautiful winery with eight apartments and a swimming pool. The agriturismo is located in the rolling hills of grain fields...

    Pool

    EUR242 to EUR327/night