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. ESTATE
    Casa Dieci

    Casa Dieci

    Poppi, AR

    Luxury hamlet in exclusive use with private pool and beautiful garden Casa Dieci consists of two luxurious holiday homes in a small borgo. You will therefore have access to two deluxe villas with heated swimming pool, air conditioning and Wi-fi in...

    Pool

    EUR396 to EUR801/night

  2. HOUSE
    Casale Paterno

    Casale Paterno

    Chianni, PI

    Detached villa with plenty of space, beautiful view and stunning pool Set in an extremely peaceful area at 30km from the town of Pisa, casale Paterno is located in an excellent position overlooking the green Tuscan landscape. The charming property...

    Pool

    EUR396 to EUR662/night

  3. VILLA
    Villa Alessia

    Villa Alessia

    Senigallia,

    Villa with private swimming pool in the hills, near the sea, panoramic view Villa Alessia is a charming villa with private swimming pool in the hills near Senigallia and only a few kilometers from the Adriatic coast. The villa is immersed in a...

    Pool

    EUR395 to EUR671/night

  4. HOUSE
    Casale Gariga

    Casale Gariga

    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

    EUR395 to EUR493/night

  5. 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

    EUR395 to EUR577/night

  6. COTTAGE
    Trulli Fico India

    Trulli Fico India

    Ceglie Messapica, BR

    Trullo surrounded by a flower garden, the patio overlooking the pool Luxury vacation home with a private pool in Puglia. It is a very well refined complex of trulli and lamie with a private 12x6 meter swimming pool set in the Ceglie Messapica...

    Pool

    EUR395 to EUR747/night

  7. HOUSE
    Villa Cignano

    Villa Cignano

    Cortona, AR

    Rustic villa surrounded by sunflower fields and vineyards with private swimming pool Villa Cignano is a former farmhouse in the Tuscan countryside between Cortona and Montepulciano. The villa is surrounded by sunflower fields and vineyards. The...

    Pool

    EUR394 to EUR504/night

  8. VILLA
    Angels House

    Angels House

    Tabiano Castello, 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

    EUR394 to EUR691/night

  9. VILLA
    Villa Luminosa

    Villa Luminosa

    Cortona, AR

    Villa at 300-m altitude, with private swimming pool and views of Cortona Villa Luminosa is a beautiful villa in the hills near Cortona. The villa enjoys a picturesque location and is surrounded by olive groves and vineyards, typical of the Tuscan...

    Pool

    EUR391 to EUR678/night

  10. VILLA
    Villa Eugenia

    Villa Eugenia

    Vicchio, FI

    Ancient Medici villa with private pool and views of the hills of Mugello This old Medici villa of around 400 m2 has undergone recent renovation work and is furnished with care. The villa is located 35 km from Florence and is situated on a...

    Pool

    EUR391 to EUR639/night

  11. VILLA
    Villa Petra

    Villa Petra

    Narni, TR

    Elegant stone farmhouse with private swimming pool in the hills of Umbria Villa Petra is an old stone farmhouse, completely renovated while maintaining the typical style of the Umbrian farms. The villa is situated in the hills with a wide view of...

    Pool

    EUR390 to EUR684/night

  12. 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

    EUR389 to EUR550/night

  13. VILLA
    Baia Riccio

    Baia Riccio

    Augusta, SR

    Gorgeous villa with whirlpool bath and breathless view, only 100m from the sea! Baia del Riccio is a beautiful villa with outdoor Jacuzzi, in a splendid sea front location, halfway between Catania and Syracuse. Set in a quiet residential complex,...

    EUR385 to EUR513/night

  14. VILLA
    Villa Sangiovese

    Villa Sangiovese

    Trequanda, SI

    Rustic villa, spa with wine bath, 2 swimming pools and stunning views Villa Sangiovese is composed of two apartments on the first floor of a rustic house. The villa is on an estate in the beautiful and unspoilt Tuscan countryside south of Chianti,...

    Pool

    EUR384 to EUR677/night

  15. VILLA
    Villa Sofia

    Villa Sofia

    Fermo, FM

    Large villa with private swimming pool in the hills, ideal for families. Villa Sofia is an attractive and spacious villa with swimming pool near Fermo, in the southern part of the Marche region. From the villa you can enjoy a beautiful view of the...

    Pool

    EUR383 to EUR716/night

  16. FARMHOUSE
    Villa Magna

    Villa Magna

    Santa Maria Della Versa, PR

    Detached villa with pool within a farm ground, in quiet hillside Completely renovated indipendent villa, located inside the grounds of a "wine resort" in a very quiet position, on the slopes of a hill in an area dotted with vineyards and well known...

    Pool

    EUR382 to EUR613/night

  17. HOUSE
    Vignabuona

    Vignabuona

    Acquaseria, CO

    Independent villa overlooking the lake, with terrace, garden and beautiful view Detached villa in a unique position, directly on the lake with pebble beach, on the most famous coast, from the tourist point of view, of Lake Como, The villa can be...

    EUR379 to EUR573/night

  18. FARMHOUSE
    Villa Boschetto

    Villa Boschetto

    Proceno, VT

    Detached villa on a hill with swimming pool, large garden and nice views This characteristic agriturismo, housing four apartments and a swimming pool, is situated in a hilly region in the Tuscia area, the land of the ancient Etruscans. The...

    Pool

    EUR379 to EUR589/night

  19. VILLA
    Villa Berta

    Villa Berta

    Cortona, AR

    Villa with private swimming pool and stunning views across hilly surroundings Villa Berta with private pool is located at 350 meters altitude in the hills north of the Etruscan town of Cortona. The villa is surrounded by 800 olive trees of the...

    Pool

    EUR378 to EUR598/night

  20. VILLA
    Villa Manganina

    Villa Manganina

    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. The villa is...

    Pool

    EUR377 to EUR644/night

  21. VILLA
    Villa Nicola

    Villa Nicola

    Ricadi, VV

    Beautiful villa is situated along one of the most charming coast-lines This beautiful villa is located in Calabria on one of the most charming coasts of the Tyrrhenian Sea, between Tropea and Capo Vaticano. The villa consists of 2 apartments and is...

    Pool

    EUR376 to EUR621/night

  22. HOUSE
    Villa Laura

    Villa Laura

    Cortona, AR

    Beautiful villa with infinity pool surrounded by beautiful Tuscan hills Villa Laura is the ideal place to spend an holiday in the spirit of the beauties of Tuscany. The Villa is situated in one of the hills that surround the Etruscan town of...

    Pool

    EUR376 to EUR547/night

  23. APARTMENT
    Piazza del Popolo

    Piazza del Popolo

    Roma, RM

    Apartment near Piazza del Popolo and Villa Borghese This beautiful apartment is on the third floor in a nice "palazzo" with lift. The apartment is cozy and nicely decorated and there is a terrace with garden furniture. The apartment is very close...

    EUR373 to EUR436/night

  24. VILLA
    Villa Simona

    Villa Simona

    Meina, NO

    Exclusive villa Lake Maggiore, with private swimming pool and own small beach. 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...

    Pool

    EUR371 to EUR394/night

  25. 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

    EUR368 to EUR595/night

  26. HOUSE
    Santo Vento

    Santo Vento

    San Fratello, ME

    Organic farmhouse with private pool and Spa with view of the Aeolian Islands 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...

    Pool

    EUR368 to EUR504/night

  27. VILLA
    Lauras

    Lauras

    Marsala, TP

    Wonderful villa with swimming pool nearby Marsala, just 5km from the sea! 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...

    Pool

    EUR366 to EUR699/night

  28. VILLA
    Villa Fulvio

    Villa Fulvio

    Pergola, PU

    Villa with private swimming pool and lots of privacy, spacious garden, barbecue and pizza oven Fulvio villa is located on a very quiet place with lots of privacy and is surrounded by beautiful countryside. The villa is decorated in a country style....

    Pool

    EUR365 to EUR554/night

  29. VILLA
    Villa Gaio

    Villa Gaio

    Vicchio, FI

    Ancient Medici villa with private pool and views of the hills of Mugello This old Medici villa of around 800 m2 has undergone recent renovation work and is furnished with care. The villa is located 35 km from Florence and is situated on a...

    Pool

    EUR363 to EUR514/night

  30. 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

    EUR362 to EUR543/night