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
    Villa Dominick

    Villa Dominick

    Positano, SA

    Villa Dominick is a beautiful holiday home on the Amalfi coast in Positano. The villa is a 10-minute walk from Piazza dei Mulini and from the main beach in Positano. Opposite the villa is the hotel of the house owner. You can use the swimming pool,...

    Pool

    $1,675 to $3,280/night

  2. HOUSE
    Giuly

    Giuly

    Gallipoli, LE

    Beautiful villa with private pool located in Gallipoli, just a few minutes drive from some of the most beautiful beaches of the Apulian Ionian coast. Ideal residence to enjoy a holiday of sun, sea and entertainment, but also of culture, Giulia is a...

    Pool

    $1,618 to $3,419/night

  3. HOUSE
    Villa Masino

    Villa Masino

    Varignana, BO

    This fine and astonishingly beautiful Villa, lies surrounded by five hectares of lush private garden, where peace and privacy are guaranteed. Among olive trees and vineyards, the tasteful dwelling, not only benefits from an excellent position but...

    Pool Pets OK

    $1,547 to $2,321/night

  4. HOUSE
    Villa Cherry

    Villa Cherry

    Cortona, AR

    Villa Cherry is a charming cottage situated in a unique location. It is immersed in the hills of Cortona with stunning views and total privacy. The villa is about 500 meters above sea level. You can spend an unforgettable holiday at this place. The...

    Pool

    $1,370 to $1,583/night

  5. HOUSE
    Moon

    Moon

    Fontane Bianche, SR

    Exclusive villa with private swimming pool that enjoys a splendid seafront position in Fontane Bianche, a popular seaside resort south of Syracuse. Surrounded by a well kept garden with lawn, this prestigious property offers spacious, well equipped...

    Pool

    $1,293 to $2,154/night

  6. HOUSE
    Boheme

    Boheme

    Taormina, ME

    Exclusive villa with private swimming pool in Taormina. Refined and prestigious, this splendid property is situated in close proximity to the Greek Theatre and to Corso Umberto, but also to a wealth of smart boutiques, restaurants and clubs that are...

    Pool

    $1,074 to $1,854/night

  7. HOUSE
    Villa Celeste 14

    Villa Celeste 14

    Fiumana, FC

    Villa Celeste is a beautiful and luxurious villa in the Emilia Romagna region. The villa is surrounded by a beautiful vineyard and consists of a villa and an annex with a panoramic swimming pool and views over Rabbi valley and the town of Forlì....

    Pool Pets OK

    $1,031 to $2,153/night

  8. HOUSE
    Cuoricino

    Cuoricino

    Siracusa, SR

    Beautiful villa with private swimming pool situated on the Maddalena peninsula, just a little bit south of Syracuse. The villa is the ideal property for those seeking a relaxing holiday, in a quiet location but near the sea, providing the perfect...

    Pool

    $990 to $1,841/night

  9. HOUSE
    Villa Gioia

    Villa Gioia

    Filottrano, MC

    Villa Gioia is a beautiful and luxurious villa for an exclusive holiday with excellent privacy. It is located in the surroundings of the beautiful beaches of the Conero. The villa is surrounded by nature and a park that is ideal for walks in the...

    Pool

    $902 to $1,499/night

  10. HOUSE
    Villa Limonaia

    Villa Limonaia

    Sinalunga, SI

    In the hills between San Gimignano and Torrita di Siena and close to Sinalunga is a special estate among olive trees, vineyards and cypress trees. The estate is situated a villa with private pool and a beautiful rural house with several apartments,...

    Pool

    $900 to $1,077/night

  11. HOUSE
    Gualtierottivilla

    Gualtierottivilla

    Pistoia, PT

    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 relaxing in the private swimming pool, surrounded by beautiful modern sculptures...

    Pool Pets OK

    $802 to $1,211/night

  12. HOUSE
    Villa Metauro

    Villa Metauro

    Montemaggiore al Metauro, PU

    Midway between the sea and the hinterland, surrounded by breathtaking countryside: this is the setting for Villa Tombolina, old summer residence of the Archbishops of Urbino, a picturesque relais with refined rooms and a warm, welcoming atmosphere....

    Pool Pets OK

    $773 to $1,183/night

  13. HOUSE
    Paternone

    Paternone

    Chianni, PI

    Casale PATERNONE is a combination of two farmhouses, built 30 m apart and offering the perfect solution for a large group wishing to spend time together without necessarily being on top of one another; each with its own pool. CASALE PATERNO is an...

    Pool Pets OK

    $748 to $1,368/night

  14. HOUSE
    Monte Amiata

    Monte Amiata

    Selva Santa Fiora, GR

    Villa Monte Amiata is a 150 year old farmhouse. It is in the heart of the Maremma area in southern Tuscany. This beautiful, hilly region has a rich artistic heritage. The villa has been carefully renovated. There is a spacious garden. The private...

    Pool Pets OK

    $726 to $947/night

  15. HOUSE
    Villa Acropolis

    Villa Acropolis

    Anzio, RM

    Villa Acropolis is a very special villa with pool in classical style located in the Anzio countryside and its well known seaside resort located in the south of Rome. Villa Acropolis is equipped with a host of amenities and is equipped to provide...

    Pool Pets OK

    $718 to $1,118/night

  16. HOUSE
    Trulli Tra Pietre

    Trulli Tra Pietre

    Ceglie Messapica, BR

    It is a large complex of luxury Trulli (more than 200m²) with a stunning natural rock carved pool. All the rooms of the villa are equipped with individually controlled air conditioning. The living area is covered with WIFI signal. The truòòo...

    Pool

    $700 to $1,128/night

  17. HOUSE
    Terranova

    Terranova

    Modica, RG

    Terranova is a luxury villa with pool located on the edge of Modica, ancient, charming, baroque town on the south-east of Sicily. Majestic and elegant, this splendid newly-built villa was designed and built to provide the ultimate comfort. The...

    Pool

    $679 to $1,253/night

  18. HOUSE
    Podere San Giovanni ventisei

    Podere San Giovanni ventisei

    Chianni, PI

    "Podere S. Giovanni is an oasis of tranquility, the old farmhouse is surrounded by the hills of Pisa and offers the opportunity to relax, take long walks, to go swimming in the lovely pool and at the same time it is really close to many cultural...

    Pool Pets OK

    $671 to $961/night

  19. HOUSE
    Villa Albizia

    Villa Albizia

    Ossuccio, CO

    Beautiful detached villa, located in a quiet residential area, 300 meters from the lake. The villa features a large landscaped garden with lawn and flowers completely enclosed, while it offers a swimming pool and a fully equipped kitchen with table,...

    Pool Pets OK

    $670 to $1,037/night

  20. HOUSE
    Villa Collina

    Villa Collina

    Magione, PG

    Villa Collina is a rustic villa and dependance with private swimming pool in the rolling hills with breathtaking views over Lake Trasimeno. The villa has a beautiful location and offers peace and relaxation. It is a perfect place for a pleasant...

    Pool Pets OK

    $667 to $1,100/night

  21. HOUSE
    Villa Pergo

    Villa Pergo

    Cortona, AR

    Villa Pergo is a beautiful stone farmhouse surrounded by olive trees and a lush garden. Near the villa is an ancient forest. The villa is located between Cortona and Trasimeno Lake on the border of Umbria and Tuscany. The private pool is slightly...

    Pool

    $663 to $837/night

  22. HOUSE
    Villa Agello

    Villa Agello

    Agello, PG

    Rustic Villa Agello, near the Trasimeno Lake, is situated at the border between Tuscan and Umbria, the two Italian regions mostly visited. The villa is a beautiful independent stone house with rectangular shape and gentle arches on the ground...

    Pool

    $660 to $1,035/night

  23. HOUSE
    Villa Celeste 8

    Villa Celeste 8

    Fiumana, FC

    Villa Celeste is a beautiful and luxurious villa in the Emilia Romagna region. The villa is surrounded by a beautiful vineyard and consists of a villa and an annex with a panoramic swimming pool and views over Rabbi valley and the town of Forlì....

    Pool Pets OK

    $655 to $1,404/night

  24. HOUSE
    Trulli Oleandro

    Trulli Oleandro

    Martina Franca, TA

    The trullo is a luxury holiday mansion in Puglia. These authentic trulli are conservatively restructured in full consideration of their old charm and have been beautifully decorated. The villa has a large private swimming pool of 14x7 meters and...

    Pool

    $653 to $1,237/night

  25. HOUSE
    Santa Fiora

    Santa Fiora

    Selva Santa Fiora, GR

    Villa Santa Fiora is a renovated farmhouse dating from 1886. It is in the heart of the Maremma area in southern Tuscany. This beautiful, hilly region has a rich artistic heritage. There is a well kept garden and a swimming pool which offers...

    Pool Pets OK

    $650 to $814/night

  26. HOUSE
    Villa Melograno

    Villa Melograno

    Arezzo, AR

    This villa is located on a wine estate in the hills near Arezzo at 550 meters altitude. The estate consists of woods and vineyards. The owner is very environmentally conscious and the wines are organic. The villa has two floors and is very elegant...

    Pool

    $647 to $1,025/night

  27. HOUSE
    Villa Torretta

    Villa Torretta

    Baveno, VB

    Just a street separates this beautiful villa from Lake Maggiore, in his most famous spot, the one in front of the Borromean Islands; the villa, with 4 floors, is located on a hillside and is set in a large park, completely fenced, with plants,...

    Pool

    $647 to $1,231/night

  28. HOUSE
    Villa Giovanna

    Villa Giovanna

    Montalcino, SI

    This delightful farm was born as an ancient Tuscan farm, the oldest part dates back to the fifteenth century we find it between Montalcino and Mount Amiata on a panoramic position, it is located within the national park of Val d'Orcia, Unesco...

    Pool Pets OK

    $627 to $748/night

  29. HOUSE
    Salinella

    Salinella

    PACECO, TP

    Salinella is a beautiful, comfortable villa with private swimming pool situated near Trapani, ancient town at the extreme western point of Sicily. The property is set on the hedge of Trapani’s saltpans nature reserve, an area where the salt has...

    Pool

    $625 to $1,093/night

  30. HOUSE
    Villa Valardegna

    Villa Valardegna

    Montepulciano, SI

    Villa Valardegna enjoys a wonderful location just 900 meters from the historic center of Montepulciano. The villa is an old and rustic farmhouse made of medieval stone. You can easily walk to the city center via a nice route. The beautiful town of...

    Pool Pets OK

    $618 to $1,478/night