Siena and Val d’Orcia

Siena and Val d’Orcia

When deciding where to stay in Tuscany, travellers find themselves in a maze… so much to see, so many renowned destinations. Well, among all Tuscan holidays, Siena holidays, are memorable offering sun-kissed days and enlightening lifestyle experiences; and, the Siena villas we can provide are among the most evocative and beautiful throughout Italy! Encased in a landscape of silky rolling hills, vineyards and olive groves, Siena rises atop three hills, connected by a network of charming winding alleys and steps, and is one of the most enchanting and celebrated Italian cities. The whole hillside boasts a variety of genuinely Tuscan villas, countryside estates and rustic farmhouses, picture-perfect holiday homes suitable for all requirements! According to ancient legends Siena was founded by Senio and Ascanio, sons of Remus founder of Rome with his brother Romolus. Though the city boasts many statues of the she-wolf feeding the twins, this is but a myth, and historians assure that the city originated from an Etruscan settlement, then Roman military outpost, and later flourished thanks to trade.


The city became important, and renowned, in the 12th century, when an independent “commune” government, which slowly started including common people, replaced the aristocratic rule. During the Middle Ages, Siena, faithful to the Ghibelline cause, and neighbouring Guelph Florence fought incessantly due to boundary issues. During the 13th and 14th century Siena became one of Italy’s most important banking centres; its power, size and wealth grew noticeably as did its magnificent artistic production with remarkable artists such as Guido da Siena, Duccio di Buoninsegna and Ambrogio Lorenzetti. It was at this time that most of the striking Sienese-Gothic architecture – for example the Duomo, the Palazzo Comunale, and the marvelous shell-shaped Piazza del Campo – that characterizes the city still today, was built. A vacation in a rental villa or farmhouse in Siena and surroundings offers visitors a splendid opportunity for a voyage into the past! Simply exploring the narrow, picturesque streets, and viewing the imposing Gothic buildings which add charm and majesty, is a memorable experience. During a Siena holiday countless gorgeous churches, museums, stunning landmarks and sites are at just a brief pleasant drive or walk from your villa’s front door! Admire Piazza del Campo, one of the world’s most fascinating squares, world-renowned for the annual Palio horse race. The square’s main landmarks are the stately 13-14th century Palazzo Comunale, which hosts the Museo Civico, crammed with masterpieces and the Fonte Gaia fountain, right in the center. And, view the gorgeous brick Torre del Mangia, tall yet delicate in design, rises right next to the Palazzo Comunale, symbolizing the palace’s power and offers breathtaking views onto the city rooftops and surrounding landscape. The Duomo (Cathedral) and the Church of Sant’Agostino well deserve a visit. The Cathedral’s red, white and green marble façade, and its inlaid marble floor are awe striking, as is the exquisite pulpit by Giovanni Pisano. Adjacent to the Duomo rises the Libreria Piccolomini, an artistic jewel: built to house the books of Pius II it is fully decorated by the great Pinturicchio’s vivid frescoes. The Church of Sant’Agostino, built in the 13th century, also boasts a rich rococo interior and frescoes by Perugino and Sodoma. A Tuscan summer holiday in a rental home near Siena will certainly include the annual Palio horse race, probably one of the world’s most exciting and heartfelt festivals! The race is an extremely popular event which all Sienese participate in wholly. The city is divided into 17 districts (“contrade”), each of which competes hoping to win the sacred banner or “palio” ; a real Sienese’s devotion to his/her contrada is total, and for the whole year Siena’s citizens prepare for the upcoming Palio. On the day all horses and jockeys are blessed in their dedicated contrada church and escorted to the square by their fans; a fascinating, hour-long historic parade in costume precedes the race itself, which is quite brief, and scenes of immense desperation and unbridled elation follow on into the night… Val d’Orcia is a dreamlike region, blessed with breathtaking beauty and countless, sublime, attractions. There are innumerable enticing things to do in Tuscany, in Val d’Orcia many of these are at their best! Wish to relax at an ancient, historic Tuscan spa? To go wine tasting in Tuscany? Longing for farmhouse holidays or gorgeous family-friendly villas in Cortona? Val d’Orcia has it all, and it’s magical! The area that extends to the south-east of Siena, setting the city’s spectacular background, is the Val d’Orcia a magical, fairytale-like land of unique landscapes. A villa or farmhouse in this region allows families or groups of friends to be fully immersed in unrivalled natural beauty and spellbinding panoramas inspired Medieval and Renaissance artists’masterpieces, and the journeys of many a foreigner, from Grand Tour travelers to writers and poets . Renting your own villa, farmstead or estate in the Val d’Orcia area means waking up to light-drenched gentle hills which melt one into another, walking through ample valleys and admiring a palette of mystifying colors, bright or subtle depending on the season, savoring tranquillity beneath the slender cypresses seem to guard the silent country roads and ancient farmhouses. Val D’Orcia is a treasure chest filled with memorable panoramas, peaceful atmospheres and century-old culture and traditions, all to be discovered on foot, horseback, bike, or leisurely driving along its quiet roads. A holiday home in Val D’Orcia offers visitors the chance to explore and dream away, discovering the rich local heritage, history and lively traditions in mysterious abbeys, majestic castles, charming ancient towns and fortified villages.. Among the most important cultural sites are the valley’s famed art towns, especially Pienza, San Quirico d’Orcia, Montalcino, Montepulciano. Pienza, created by Enea Silvio Piccolomini (Pope Pius II) to be the “ideal” or “utopian” city, is a rare example of an actual Renaissance town. Its exquisite city center boasts marvelous landmarks, such as the main square, the Duomo and Palazzo Piccolomini with its magnificent gardens. San Quirico d’Orcia, with its splendidly preserved walls and turrets, is a superb example of Medieval walled village, and hosts important churches. Montalcino, world-celebrated as birthplace of the prized Brunello wine, rises imposingly atop a hill surmounted by its majestic 13th century fortress, offering gorgeous palaces, precious artwork and fascinating winding alleys full of quaint workshops and gastronomic specialty shops. Montepulciano, surrounded by grand 15th century walls and fortifications built by the great Antonio Sangallo the Elder, is renowned as hometown of the Tuscan “Vino nobile” wine and for its magnificent Renaissance palaces. The area also features innumerable delightful villages characterized by spectacular views, quiet stone-paved squares and picturesque narrow alleys. Visitors accommodated in Val d’Orcia holiday villas have the chance to easily travel to the amazing ancient fortresses in Radicofani and Castiglione D’Orcia and discovering the amazing natural Spa in Bagno Vignoni. Visiting this spellbinding village is a journey back in time: it houses a great walled basin of steaming hot water in the main square, where great men like Lorenzo the Magnificent used to bathe! Families with children delight in Val d’Orcia: its wide variety of family-friendly estates, villas and farmhouses and enticing daily excursions! To the region’s striking, mysterious abbeys, for example, Sant’Antimo and San Galgano, awesome sites with incredible legends. Sant’Antimo, which boasts a lovely Romanic church immersed in the verdant surrounding countryside, is said to have been built on order of Charlemagne himself. Legends say he and his army were travelling back to France when they risked contracting the plague; they were spared and to render his thanks the Emperor set the first stone of the Abbey. San Galgano is a unique destination for all travelers, and a must-see for children. Nestled among the rolling hills between the villages of Monticiano and Chiusdino, lie the wonderful, dream-like ruins of this impressive Abbey, a spectacular place where the “floor” is a meadow of grass, there is no roof at all and, above all there is a real sword in the stone! Finally, another truly interesting site is La Foce Estate, owned by the descendants of Anglo-American writer Iris Origo and vividly described in her famous diary “War in Val D’Orcia”. The estate’s gardens – open to the public on Wednesday afternoons – are exquisite. Designed by Cecil Pinsent in the 1920s the park features a formal Italian garden divided by box hedges with lemon trees. A rose garden, wisteria-covered pergola bordered by lavender hedge, fruit trees and bushes of wild broom, thyme and rosemary, enhance its splendor.

Villa Prode

This exceptional luxury Tuscan home has been carefully crafted to weave luxury and comfort into a genuine Italian experience.

Villa Fara

The villa, originally commissioned by the illustrious Chigi family and designed by the renown Sienese architect Baldassare Tommaso Peruzzi, has been extended and enhanced over the centuries, and has recently undergone a complete restoration whilst remaining faithful to the original design.


A stunning village residence rising in an outstanding position completely surrounded by Val d’Orcia’s fairy-tale-like rolling hills, immersed in luxuriant vegetation and caressed by sweet-scented breezes, the property is strategically located at just a few steps from the village center.

Villa Pomina

This stunning property is located in the heart of Valdorcia, that evocative stretch of land represented in every Tuscany postcard, ten kilometres from Siena, with a commanding view over the cypresses lines all around. The estate, featuring a vegetable garden thought for chefs and a number of alfresco area distributed on the private curated grounds, stands on the top of a hill, walking distant from a village with a trattoria, a local restaurant with typical ingredients and dishes from the Senese culinary tradition, and it has been planned to become a contemporary, instagrammable, mansion among a traditional setting.

Villa La Loggia

A magnificent environment-friendly 17th century Tuscan country villa with extensive private grounds located in a striking panoramic position Rising right on the top of a hill in the open countryside of Siena, within easy reach of the Chianti area, the main art cities such as Florence and San Gimignano and most charming and interesting Tuscan towns - Montalcino, Montepulciano and Pienza - Villa La Loggia is an ideal oasis-like retreat to set off from to explore the surroundings.

Villa La Selva – The Solata Apartment

Rising in a superb position of the Tuscan countryside, amidst vineyards and olive groves, Villa La Selva is an extensive wine estate (producing SuperTuscans and a delectable Vin Santo) which offers several different vacation homes: a master villa and a “Casa Colonica”, the typical Tuscan farmhouse, dating back to the 16th century. The estate includes grounds and vineyards, the estate wine shop and the owners’ villa, two swimming pools, a tennis court and a bocce court. The farmhouse is truly charming, beautifully restored and splendidly refurbished, it offers cozy and genuine Tuscan accommodation in 4 exquisite independent apartments. The charming Solata apartment is the largest, accommodating up to 6 guests. Offering heavenly views, dazzling grounds, an authentic atmosphere at a brief scenic drive from the countless attractions of Tuscany’s art cities and picturesque villages, Villa La Selva provides the ideal premises for an unforgettable Tuscan vacation!”

Villa La Selva – Guardia Apartment

Rising in a superb position of the Tuscan countryside, amidst vineyards and olive groves , Villa La Selva is an extensive wine estate (producing SuperTuscans and a delectable Vin Santo!) which offers several different vacation homes: a master villa and a “Casa Colonica”, the typical Tuscan farmhouse, dating back to the 16th century. The estate is comprised of grounds and vineyards, the estate wine shop and the owners’ villa, two swimming pools, a tennis court and a bocce court. The farmhouse is truly charming, beautifully restored and splendidly refurbished, it offers cozy and genuine Tuscan accommodation in 4 exquisite independent apartments. The charming Guardia apartment accommodates up to 6 guests. Offering heavenly views, dazzling grounds and an authentic atmosphere at a brief scenic drive from the countless attractions of Tuscany’s art cities and picturesque villages, Villa La Selva provides the ideal premises for an unforgettable Tuscan vacation!”

Villa Amiata

Villa Amiata, a lovely vacation villa named after the breathtaking view from the villa: the stately presence of Mount Amiata, imposing among the surrounding gently rolling hills. Located in enchanting Val d’Orcia, the villa is part of the extensive Monteverdi estate and offers stylish, extremely comfortable accommodation in a magnificent setting. Ideal for relaxing, leisurely vacations, Villa Amiata is also an ideal starting point for exciting visits of the area. Villa Amiata Monteverdi… a dream vacation villa, for an unforgettable Tuscan holiday!

Villa San Pietro

Part of the splendid extensive Monteverdi estate, Villa San Pietro is an exquisite 2 bedroom luxury villa. Perfect for a small family or party of friends, it is located in the midst of Val d’Orcia’s soft hillside, surrounded by spellbinding views. Providing stylish, extremely comfortable accommodation in an exclusive setting, Villa San Pietro is ideal for leisurely vacations and also the perfect starting point for exciting visits of the area. Villa San Pietro Monteverdi… the vacation home for an enlightening Tuscan experience!

Villa La Selva – Main Villa

Rising in a superb position of the Tuscan countryside, amidst vineyards, olive groves and green fields, Villa La Selva is a splendid wine estate, producing SuperTuscan wines and a delectable Vin Santo. The property offers several charming homes for authentic Tuscan vacations. The property, privately owned and managed, is a marvelous vacation retreat. The extensive grounds include a bountiful orchard, green fields and resplendent vineyards, and host the estate wine shop (and the owners’ villa) as well as two swimming pools, a tennis court and a bocce court. The main villa is a restored Medici country house: a perfect example of an aristocratic countryside mansion. Splendidly furnished, it boasts luxurious facilities and an elegant yet genuine atmosphere. Offering heavenly views, dazzling grounds, an authentic atmosphere, all at a short drive from the countless attractions of Tuscany’s art cities and picturesque villages, Villa La Selva provides the ideal premises for an unforgettable Tuscan vacation!

Villa Ferraia

A beautiful estate framed by the magical rolling hills of Siena. Fully immersed in the Natural Reserve of Tocchio, surrounded by shady woods and peaceful fields, this extraordinary property offers lovely, rustic ambiance and outstanding in-house facilities: horseback riding, swimming pool, sauna and fitness center and hot/cold pools in the garden. The most amazing feature is: a unique private astronomic observatory for star sightings. Villa Ferraia is the ultimate dream vacation home, ideal for family reunions, fun-loving friends’ parties or memorable fairytale-like celebrations.

Villa Alberica

Villa Alberica is an authentic, characteristic Tuscan home, fully immersed in the luxuriant, unspoiled green countryside. Located close to San Casciano dei Bagni’s picturesque town center, and world-renowned Spas, Villa Alberica is a spacious privately owned countryside home rich in the charming rustic appeal and genuine character of the typical Tuscan “casa colonica”. Stylishly restored and refurbished, the villa blends state of the art facilities, up to modern needs and expectations, with original period architecture and furnishings. The whole estate is gorgeous, with ample areas, ideal for outdoor activities and sports, relaxing and entertaining. A vacation at Villa Alberica is not a simple holiday, it is an authentic Tuscan lifestyle experience.

Villa Vale

Villa Vale is an extensive, splendid estate rising in Val d’Orcia, one of Tuscany’s most magical areas. Fully immersed in a mesmerizing landscape of softly rolling hills dotted with silvery olive groves and spectacular vineyards, the property is surrounded by exquisite villages, all to be discovered, and countless hiking and biking paths. Villa Vale is the ideal holiday home for families and groups of friends

Villa Muri Antichi

Villa Muri Antichi (namely “ancient walls”) is a gorgeous villa superbly set in one of Tuscany’s most evocative areas, on the top of a hill (at 900 meters) with a magnificent view of the valley below, in the enchanting Val d’Orcia. The villa, surrounded by spellbinding landscapes, is part of the extensive Monteverdi estate (which includes other private villas as well as a boutique hotel) and offers top-notch accommodation in a truly exceptional location. Ideal for relaxing, vacations, Villa Muri Antichi is also the perfect starting point for enticing visits of the area’s many attractions. A splendid venue for an enlightening Tuscan experience.

Villa Romantica

Rising in a sublime spot of magical UNESCO world heritage site Val d’Orcia, immersed in a dreamlike landscape and surrounded by luxuriant vegetation, Villa Romantica is a wonderfully restored 19th century farmhouse. Transformed into a splendid and serene retreat it is a peaceful haven, iconically romantic. Nearby, countless evocative heritage-filled villages offer visitors the most authentic of Tuscan experiences. Villa Romantica is an ideal location for an unforgettable Tuscan holiday!

Podere Zingoni

Relish Val d’Orcia’s dreamlike atmosphere, fabulous views and leisurely lifestyle during an unforgettable holiday at Podere Bachicche. This fascinating privately owned estate, strategically located close to the area’s most picturesque villages, is the perfect location for country vacations and sightseeing. The villa is genuinely charming, and complete of all facilities. Immersed in 30 acres of lovely private woods it boasts genuine Tuscan charm and offers a variety of outdoor spaces and a lovely swimming pool

Podere Rombolino

Perched atop a gentle hill immersed in Val d’Orcia’s fairytale-like landscapes, rises Podere Rombolino. This gorgeous estate is an ideal, charming, retreat to fully experience the peaceful, leisurely rhythms of typical Tuscan lifestyle. A picture-perfect home away from home.

Podere Palazzolaccio

Podere Palazzolaccio is a soothing oasis in the midst of magical Val d’Orcia’s greenest heart, located close to Umbria’s and Tuscany’s most picturesque towns. The estate, privately owned, is comprised of a stunning 300-year old farmhouse surrounded by oak tree woods, cypresses and silvery olive groves. The whole property offers natural, rustic elegance, spellbinding views and the opportunity to live the countryside’s unhurried lifestyle and engage in the many activities in the surroundings. A vacation at Podere Palazzolaccio is authentic Tuscan enchantment.

Cantine di Cerreto

Dreamlike landscapes crowned by bright blue skies, luxuriant vineyards and the chirping of countless birds… evocative villages, rich in a thriving heritage of century-old traditions and quiet marble-paved parish churches. Le Cantine di Cerreto, a gorgeous estate and its 17th century villa, rise immersed in the oasis-like scenario of the Chianti hills, strategically located at just 20 minutes from Siena. An authentic and charming estate, a peaceful haven and the ideal retreat for a memorable Tuscan vacation.

Podere Casellaccia

In the greenest heart of Val d’Orcia’s harmonious countryside, caressed by crisp, sweet-scented breezes and the chirping of birds, rises Podere Casellaccia, a charming ancient rural estate, offering a spacious Villa and luxuriant grounds. A soothing oasis, an ideal retreat for unforgettable, authentic, Tuscan vacations.