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
    Trulli Country Golf

    Trulli Country Golf

    Gioia del Colle, BA

    Wonderful complex made up by 11 rural ancient trulli with a big swimming pool (14x7 mt) and a Pitch & Putt nine-holes amateur golf course, fully illuminated also for the night game. The trulli are perfectly restored and equipped with lovely...

    Pool

    $694 to $1118/night

  2. 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

    $688 to $837/night

  3. 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

    $686 to $1096/night

  4. 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

  5. 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 $1037/night

  6. 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 $1100/night

  7. HOUSE
    Villa Veronica

    Villa Veronica

    Cortona, AR

    Villa Veronica is a fully restored farmhouse in the middle of Valdichiana close to the Etruscan city of Cortona. The area consists of cornfields and sunflowers. The villa has wooden beams on the ceiling, brick arches, wrought iron beds and wooden...

    Pool

    $661 to $963/night

  8. 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 $1404/night

  9. 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 $1237/night

  10. 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

  11. 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 $1025/night

  12. 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 $1231/night

  13. HOUSE
    Villanovia

    Villanovia

    Volterra, PI

    Villanovia is a fully renovated country property, inside a natural park, with a 360° amazing panorama. It overlooks the cities of Volterra and Pomarance, the Metallic Hills of Larderello and untouched forest and farm scenarios. The house has...

    Pool

    $636 to $1093/night

  14. 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

  15. 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 $1093/night

  16. HOUSE
    Villa Nella

    Villa Nella

    Cortona, AR

    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 house consists of two floors and an external staircase leads to the upper floor....

    Pool

    $613 to $850/night

  17. HOUSE
    Villa Carpaneto

    Villa Carpaneto

    Carpaneto Piacentino, PC

    Villa Carpaneto is a villa with private pool and large garden in the hills of Piacenza. The garden is about 10,000 square meters and provides a breathtaking view of the hills. The villa is about 300 meters and a 10-minute drive from Carpaneto...

    Pool

    $605 to $701/night

  18. HOUSE
    La Villa

    La Villa

    Cisternino, BR

    Feel the sheer pulse where an ancient rural farmhouse, sea, and olive trees collide. Built to help the local peasants with the harvest. Having changed very little in the past 100 years, it remains a true and authentic experience. The Villa's...

    Pool

    $604 to $771/night

  19. HOUSE
    Villa Giuliana

    Villa Giuliana

    Castiglion Fiorentino, AR

    Villa Elena with private pool is located in the middle of the Tuscan countryside and a short walk from the historic center of the beautiful town of Castiglione Fiorentino. The stone villa is surrounded by olive trees and cypresses that dominate the...

    Pool Pets OK

    $597 to $870/night

  20. HOUSE
    Le Edicole

    Le Edicole

    Ragusa, RG

    Le Edicole is a splendid villa with pool immersed in beautiful countryside, near the Donnafugata Castle, on the road that from the baroque town of Ragusa leads to the sea. This characteristic, country property has been expertly restored and...

    Pool Pets OK

    $593 to $1127/night

  21. HOUSE
    Casettauno

    Casettauno

    Vinci, FI

    Set among the verdant Montalbano hills, this farm is located in the heart of Tuscany, just a few kilometres from the most beautiful and striking places in the region. Thanks to the local road network, visitors can easily reach cities including Pisa,...

    Pool Pets OK

    $586 to $938/night

  22. HOUSE
    Villa Pepi

    Villa Pepi

    Rignano Sull'arno (fi), FI

    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 Villa (early 17th Century)is the place to be. The house sits high on a hill in...

    Pool Pets OK

    $585 to $998/night

  23. HOUSE
    Villa Ambra

    Villa Ambra

    Cortona, AR

    Villa Ambra is located at 400 mt in the hills east of Cortona. The villa is surrounded by olive trees and from the villa you have a beautiful view over the whole of Valdichiana. The exterior walls of the villa are covered with ivy which turns red in...

    Pool Pets OK

    $583 to $783/night

  24. HOUSE
    Villa Isabella

    Villa Isabella

    Cortona, AR

    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 preserved with wood beams and terracotta floors. You enter the villa through a large...

    Pool

    $581 to $902/night

  25. HOUSE
    Villa Milivita

    Villa Milivita

    Monopoli, BA

    Itis a luxury mansion with four large bedrooms, featuring a saltwater swimming pool of 14x7m. The villa is sized 250m² on two levels and is situated in the peaceful countryside of Monopoli in Puglia on a beautiful 10.000m² piece of land. The...

    Pool

    $579 to $1126/night

  26. HOUSE
    Villa Cozzo

    Villa Cozzo

    Terrasini, PA

    Don't look any further! From this villa, you'll have a perfect holiday on this sunny island. It's a villa, completely built and arranged in Sicilian style. First of all, it reveals, in its most intimate side, the strong cohesion and personality of...

    Pool

    $571 to $783/night

  27. HOUSE
    Palazzo Antico

    Palazzo Antico

    Montepulciano, SI

    This beautiful, spacious villa is surrounded by vines and is located on the top of a hill from where you can enjoy beautiful panoramas. The villa has a beautiful green garden with fruit trees where you can relax. Under the veranda there is a large...

    $569 to $608/night

  28. HOUSE
    La Selvicciola

    La Selvicciola

    Terricciola, PI

    A typical farmhouse on "top of the hill", surrounded by vineyards and fields with a large swimming pool that reflects the warm colors of the Tuscan countryside. Ideal for a group of friends who want to spend a holiday in the beautiful Tuscan...

    Pool Pets OK

    $569 to $1086/night

  29. HOUSE
    Villa Rosso

    Villa Rosso

    Badia al Pino, AR

    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 a beautiful covered terrace. The pool is in a sunny position and there...

    Pool

    $568 to $795/night

  30. HOUSE
    Podere San Giovanni

    Podere San Giovanni

    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

    $562 to $821/night