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
    Fienile

    Fienile

    Paciano, PG

    This beautiful farmhouse complex is 2 km from Paciano and on the border of Umbria and Tuscany. It is 700m above sea-level. The farmhouse is in the middle of the Monte Pausillo National Park. The old farm has been completely renovated. It now...

    Pool Pets OK

    $77 to $109/night

  2. VILLA
    Vecchia Dimora Resort

    Vecchia Dimora Resort

    Centuripe, EN

    Elegant, historical villa with swimming pool in rural region near Etna 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...

    Pool

    EUR346 to EUR584/night

  3. HOUSE
    Falcons Glen Home #12950

    Falcons Glen Home #12950

    Naples, FL

    Golf Course CommunityTee off in your own backyard! This home has it all!!! The home is on the second hole ( par 5 ) of Flamingo 150 yards out from the green with an incredible wide view of the course. Take a long walk on the nature trail, or jump in...

    Pool

    $215 to $520/night

  4. HOUSE
    Casa Il Vivaio

    Casa Il Vivaio

    Carmignano, PO

    Beautiful house with authentic atmosphere at wine estate on mountain. This beautiful property is located in a wine region. Stay in one of the country houses which are located in a wing of the manoir. The house was originally built as a hunting lodge...

    Pool

    EUR170 to EUR194/night

  5. FARMHOUSE
    Casa Rimessa

    Casa Rimessa

    Sellano, PG

    Pretty farmhouse in hilly estate for four people This beautiful apartment for four people lies on the ground floor and is situated in an old restored farm house on a hilly landscape, where there's also a castle as well as several other farm houses....

    Pool

    EUR53 to EUR117/night

  6. FARMHOUSE
    Fienile

    Fienile

    Bucine, AR

    Home with a swimming pool in a central location in Tuscany This holiday destination is situated in the heart of Tuscany in the hills around the Ambra valley. The agritourism consists of a group of old farms that have been completely renovated and...

    Pool

    EUR108 to EUR216/night

  7. HOUSE
    Villa Buteo

    Villa Buteo

    Popolano Maradi, FI

    Farmhouse in the middle of nature with swimmingpool The farmhouse has common rooms on the ground floor where you may choose to rest and read, to play snooker on an antique billiards table, bake bread in the wood-fired oven or grill dinner to enjoy...

    Pool

    EUR265 to EUR389/night

  8. HOUSE
    Di Vinci

    Di Vinci

    Vinci - Florence, FI

    Typical Tuscan farmhouse with private pool in the hills of Vinci 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...

    Pool

    EUR355 to EUR567/night

  9. ESTATE
    Podere

    Podere

    Rapolano Terme, SI

    an authentic water mill with elegant apartments. 1 km from Rapolano Terme, in the midst of the Tuscan landscape amidst the olive trees and ancient oaks, you will find an old watermill. Next to the mill there is a stream which was previously used by...

    Pool

    EUR137 to EUR248/night

  10. FARMHOUSE
    Le Balze

    Le Balze

    Pian di sco, AR

    Agri-tourism with all the special charm of rural Tuscan life. In one of the loveliest parts of Tuscany, Chianti Fiorentino, there is an agri-tourism site of 4 apartments, commanding fine views. The agri-tourism site has been carefully renovated...

    Pool

    EUR90 to EUR167/night

  11. COTTAGE
    Giardino- Taverna Piccola

    Giardino- Taverna Piccola

    Terranuova Bracciolini, AR

    Colours and scents from Tuscany await you in this wonderful property The country house, just on the slopes of the Pratomagno Mountain, is really a hidden angle of the wonderful Tuscan countryside, offering beautiful views over the colourful hills....

    Pool

    EUR155 to EUR176/night

  12. FARMHOUSE
    Nonno Raoul

    Nonno Raoul

    Ortignano, AR

    Apartment near swimming lake, large garden and beautiful surroundings Agriturismo Nonno Raoul is situated right in the middle of the Casentino valley woodlands. The agriturismo is part of an agricultural farm set in 350-hectare grounds with a small...

    Pool

    EUR79 to EUR131/night

  13. HOUSE
    Da Vinci Tre

    Da Vinci Tre

    Vinci, FI

    Nice apartment in the area of Vinci This apartment ( ground floor) is located in a typically Tuscan agriturismo in the area of Vinci. The agriturismo (6 different apartments in total) also offers a cosy garden with barbecue and a swimming pool, with...

    Pool

    EUR110 to EUR174/night

  14. FARMHOUSE
    Rossellino

    Rossellino

    Reggello, FI

    Holiday home in calm surroundings with unspoiled nature This structure is a truly beautiful place with its large swimming pool surrounded by nature, the lawn where the children can play and where they even have their own swimming pool with low water...

    Pool

    EUR121 to EUR197/night

  15. ESTATE
    Camillo Tosco

    Camillo Tosco

    Chianacce, AR

    Villa with private pool, between Montepulciano and Trasimeno Villa Camillo & Tosco is situated between Montepulciano and Lake Trasimeno. The villa consists of 2 spacious apartments. There is garden furniture and a swimming pool in the garden. The...

    Pool

    EUR200 to EUR410/night

  16. HOUSE
    Villa Vivai

    Villa Vivai

    Dicomano (fi), FI

    Detached holiday home with swimming pool and vineyard 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 holiday...

    Pool

    EUR170 to EUR401/night

  17. HOUSE
    Rosina

    Rosina

    Cecina di Larciano, PT

    Apartment on a farm immersed in nature and equipped with swimming pool In the heart of Tuscany, in the foothills of Mount Montalbano, the ideal farm stay opens its doors for your unforgettable holidays in the Tuscan countryside, or for a simple...

    Pool

    EUR154 to EUR214/night

  18. HOUSE
    Biancospino

    Biancospino

    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

    EUR86 to EUR126/night

  19. HOUSE
    Fienile

    Fienile

    Colle val D'elsa, SI

    Farm holiday with swimming pool in the hills of the Chianti, beautiful surroundings This agriturismo is located in Colle di Val d'Elsa, in a medieval borgo in the middle of the Chianti hills. The borgo consists of various rustic houses and a garden....

    Pool

    EUR143 to EUR260/night

  20. HOUSE
    San Francesco Tre

    San Francesco Tre

    Orciatico, PI

    Stunning apartment on the estate from the 13th century, of a noble family This beautiful apartment is, together with 4 others, part of a charming agriturismo. The estate has been owned by the noble Paoletti Gualandi family since the 13th century,...

    Pool

    EUR84 to EUR136/night

  21. HOUSE
    Agriturismo Foiano Il Granaio

    Agriturismo Foiano Il Granaio

    Castiglion Fiorentino, AR

    Cosy and snug apartment surrounded by nature 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 the...

    Pool

    EUR106 to EUR177/night

  22. HOUSE
    l'Istrice

    l'Istrice

    Cutigliano, PT

    Apartment with beautiful views. This new apartment complex is 2 km from the medieval town of Cutigliano in the Apennines. The town is 900 metres above sea level. There are twelve apartments in the complex. They are tastefully and carefully...

    Pool

    EUR111 to EUR134/night

  23. FARMHOUSE
    Agriturismo Nonno Raoul

    Agriturismo Nonno Raoul

    Ortignano, AR

    Farmhouse near swimming lake, large garden and beautiful surroundings Agriturismo Nonno Raoul is situated right in the middle of the Casentino valley woodlands. The agriturismo is part of an agricultural farm set in 350-hectare grounds with a small...

    Pool

    EUR89 to EUR314/night

  24. VILLA
    Villa Mara

    Villa Mara

    Cortona, AR

    Nice villa with private pool, large garden, lots of privacy and close to Cortona Villa Mara is immersed in the green hills near the ancient Etruscan city of Cortona. Cortona is considered one of the most beautiful villages in Italy in a rolling...

    Pool

    EUR327 to EUR657/night

  25. VILLA
    Villa Rosso

    Villa Rosso

    Badia al Pino, AR

    Tasteful villa with rose garden, swimming pool and golf training course Villa Rossa is a prestigious and tasteful villa near Arezzo. The owner has decorated the house with great passion. The villa is surrounded by a lush garden with rose bushes and...

    Pool

    EUR527 to EUR735/night

  26. APARTMENT
    Chianti Village Morrocco T4

    Chianti Village Morrocco T4

    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

    EUR262 to EUR338/night

  27. HOUSE
    Camino

    Camino

    San Casciano in Val di Pesa, FI

    Cozy apartment in a farmhouse with swimming pool, in the Chianti area Our infinite passion for Tuscany and wine leads us to welcome tourists from all around the world at the best of our possibilities, offering you our best prices for a unique and...

    Pool

    EUR119 to EUR170/night

  28. HOUSE
    Casa Padronale

    Casa Padronale

    Modigliana, FC

    Apartment in the green of the vineyards with swimming pool. The apartment is surrounded by 6 hectares of vineyard of the agriturismo (with Sangiovese, Cabernet Sauvignon and Merlot) about 350 meters above the sea level. The apartment has its...

    Pool

    EUR178 to EUR209/night

  29. VILLA
    Villa Pepi

    Villa Pepi

    Rignano Sull'arno (fi), FI

    Set in breathtaking landscape just outside Florence with lovely garden and pool If you wish to spend some time in Tuscany in the best way possible and experience the feeling of belonging in this beautiful spot, no other guests around, historical...

    Pool

    EUR522 to EUR942/night

  30. FARMHOUSE
    Fizzano Bilo

    Fizzano Bilo

    Poggibonsi, SI

    Rustic Tuscan hamlet with swimming pool, among the Chianti vineyards In the heart of the Chianti Classico, surrounded by vineyards and olive groves is a small Tuscan hamlet, well known for its fine wines. The hamlet dates back to the eleventh...

    Pool

    EUR210 to EUR247/night