Pienza Vacation Home Rentals

On your next trip, consider a Pienza vacation home rental for your accommodations. There are 1 vacation homes in Pienza resorts. Vacation home rentals are generally appealing for many reasons. Some of the foremost being cost savings, more space, and no tips or service charges that are associated with hotel rooms. Vacation rental homes have kitchens for cooking, living rooms for gathering together and offer the appeal of living in a real neighborhood and soaking up the rhythm of the locals.

With our friendly, responsive customer service and extensive informational website, renting a Pienza vacation home from Owner Direct Vacation Rentals is a breeze. Find your perfect location and home size to suit your needs, no matter what your criteria.

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  • A Villa and Historic Garden in the Magical Val D'orcia, Tuscany

    A Villa and Historic

    Pienza: Villa
    • 11 BDR
    • 8 BA
    • Sleeps 19
    • #206835
    €3,333 to €3,333 EUR/night  
    This Villa has been described as "a crossroad and meeting place in the heart of Tuscany for all those who delight in nature, literature, the arts, and history, in a setting of perfect harmony". It has been featured in the Financial Times top 10 Travel destinations 2012. The Villa lies on the hills overlooking the Val d'Orcia, now a UNESCO World Heritage site. Midway between Florence and Rome, it is also within easy reach of Siena, Arezzo, Perugia, Assisi, Orvieto. Renaissance and medieval gems such as Pienza, Montepulciano, Monticchiello and Montalcino are only a few miles away. The countryside abounds in lovely walks among woods and the characteristic "crete senesi" (clay hills); the food is among the best in Tuscany and famous wines such as the Vino Nobile and Brunello can be tasted in the local cellars. Tuscany's charms have been widely publicized, but the Villa is undoubtedly a place where you can enjoy the very best of this region. The Villa itself (now available for rent) was built in the late 15th century as a hostel for pilgrims and merchants travelling on this busy road. In 1924 the property was bought by Antonio and Iris Origo (the renowned writer), who dedicated their lives to bringing progress and social change to this poverty-ridden land. Today the estate, a combination of woods, cultivated fields and olive groves, is run by the Origo daughters, Benedetta and Donata. The garden, designed by the English architect Cecil Pinsent, is considered an ideal combination between the natural landscape and XXth-century architecture, blending Italian and English traditions and taste. The Villa was originally built at the end of the XVth century as a wayside tavern, but soon became the centre of an estate belonging to the great Hospital of Santa Maria della Scala in Siena. In 1924 it was bought by Antonio and Iris Origo and turned into their comfortable home, from where they farmed and developed the land. Three gardeners look after the premises, including the swimming pool opposite the ‘limonaia’ (orangerie). Two full-time maids (including a local cook) care for the house and its inhabitants. Meals are often held under the pergola in the garden, where guests relax in the shade of roses and wisteria, lulled by the sound of water from the fountain nearby, or by the swimming pool. The Villa has also become a center for cultural and artistic activities. Castelluccio, a medieval castle on the property, is the home of an international music festival, "Incontri in Terra di Siena", held in July. The Villa is a perfect venue for celebrations, weddings, or any kind of event: Benedetta Isidori will cater to all your needs, in perfect English. Renting this Villa is a way of discovering the Val d'Orcia at its most intimate. Our guests are captivated by the spirit and lifestyle that have developed here over the last 80 years. Come and share our traditions!
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  • Two Bedroom Detached Villa with Enclosed Grounds and Swimming Pool

    Two Bedroom Detached Villa

    San Gimignano: Villa
    • 2 BDR
    • 3 BA
    • Sleeps 8
    • #201154
    €103 to €264 EUR/night Credit Card Pet Friendly
    <b>Local charges noted below are paid on arrival and are NOT included in the quote provided by Owner Direct - Heating Euro 10 per day if used Air conditioning Euro 15 per week Wi Fi internet access Euro 15 per week payable locally and must be requested in advance at time of booking. Accommodation tax from 1st March to 31st October, Euro 1,50 per person per night (max 5 night) children under 12 years free of charge</b> A beautiful detached restored barn with private swimming pool, surrounded by its own well kept garden with wonderful views over vineyards and cypress groves towards medieval San Gimignano visible in the distance. Immersed in the countryside yet only 2 km from the town, the villa provides very high standard secluded accommodation in a much sought after area of Tuscany. Built on a slope, the accommodation is on three floors, all connected by internal staircases, but each floor actually opens on to an area of the garden. Originally a hayloft, the house has been carefully restored preserving original characteristics, such as slanted brick windows in the spacious bedrooms, terracotta floors, beamed ceilings and brick archways, all so typical of Tuscan country architecture. There are 3 shower rooms, one on each floor, and 2 fully equipped kitchens ensure modern comfort, yet marrying perfectly with the classic furniture. Both living rooms have comfortable sitting areas with settees which can convert to double beds on request, and the lounge on the ground floor also has a characteristic fireplace, a specially commissioned hand painted mural depicting the beautiful landscape, and arched patio doors which open onto the large patio and garden. Within the well kept grounds close to the house is the large swimming pool (14m x 7m) which is private to the villa and has a lovely view over the countryside. The house and its garden is fully enclosed, and has its own parking area. It is only 2km from San Gimignano and its selection of shops and excellent local restaurants, and many of the regions other sights are within easy driving distance. Florence and Siena are both easily accessible via main road and rail links from nearby Poggibonsi.
  • Lovely Cottage for 2 to 4 People on a Pretty Estate with Swimming Pool.

    Lovely Cottage for 2 to 4

    San Gimignano: Cottage
    • 1 BDR
    • 1 BA
    • Sleeps 4
    • #201138
    €49 to €86 EUR/night Credit Card Pet Friendly Star Rating
    A pretty detached cottage on a lovely estate close to San Gimignano, it has a large private terrace with pretty views of the medieval town of San Gimignano silhouetted on the hillside. Also on the estate is a pretty swimming pool surrounded by sun terrace and garden. Light and airy, this pretty cottage enjoys a delightful atmosphere. It has all its accommodation on the ground floor below there is only a basement floor and at the rear a storage barn. Comfortably furnished the living area has a traditional wood burning fireplace, settee/sofa bed, kitchen/dining area and glass doors opening on the terrace. There is also a double bedroom and shower room. A barbecue, utility room with washing machine, and metered telephone are available for communal use and parking is in the grounds near to the cottage.
  • Four Bedroom Detached Villa San Gimignano

    Four Bedroom Detached

    San Gimignano: Villa
    • 4 BDR
    • 4 BA
    • Sleeps 11
    • #148259
    €185 to €371 EUR/night Credit Card Star Rating
    This is the perfect example of a Tuscan country villa, it is surrounded by mature gardens and has a large private swimming pool with a fantastic panorama of the surrounding countryside. Incredibly although the villa is immersed in all this peace and tranquillity, medieval San Gimignano, which is a joy to explore, is only 10 minutes walk away. Beautiful views of the surrounding coutryside all around. Rolling hills with olive groves and vineyards.
  • Togna Self Catering Apartment in the Cottage

    Togna Self Catering

    Gaiole in Chianti: Villa Vistarenni: Cottage
    • 2 BDR
    • 1 BA
    • Sleeps 4
    • #40566
    €195 to €220 EUR/night Credit Card
    Just a few steps lead to the flat on the first floor of the 16th century cottage in natural stone. From the windows you can enjoy the view over the swimming pool and breathe the scent of the plants in the garden underneath. The room with incredible French canopy beds gives to the simple and rural style an elegant touch. The living room with fireplace provides a friendly environment for pleasant evenings in the stillness and peace of Chianti.
  • Chiara self catering apartment

    Chiara self catering

    Gaiole in Chianti: Villa Vistarenni: Cottage
    • 3 BDR
    • 1 BA
    • Sleeps 6
    • #40564
    €220 to €240 EUR/night Credit Card
    Farmhouse of the 16th century built on local stone, adjacent to the villa and very close to the swimming pool. At one side of the house there is a garden with typical Mediterranean plants, including lavender, santolina and rosemary. This flat is located on the ground floor of the cottage and is connected through a French door to a small, cool private garden equipped for enjoyable outdoor breakfasts or candlelit dinners. Each bedroom is painted in pastel colours and the fireplace in the living room will make you feel at home.
  • Casina Studio- Self Catering Apartment

    Casina Studio- Self

    Gaiole in Chianti: Villa Vistarenni: Cottage
    • 1 BA
    • Sleeps 2
    • #40565
    €100 to €110 EUR/night Credit Card
    This pretty studio apartment is located on the rear ground floor of the cottage and has its own small equipped garden where you may choose to have your meals outdoors and enjoy the peaceful site. Simple and cozy, it is an ideal nest for couples wishing to rest and surrender themselves to the magic of Tuscany and the Chianti hills.
  • Charming Independent Villa in Tuscany with Pool and 3 Bedrooms

    Charming Independent Villa

    Sinalunga: Villa
    • 3 BDR
    • 3 BA
    • Sleeps 8
    • #208441
    €254 to €319 EUR/night Paypal Pet Friendly
    Nice farmhouse and outbuilding dating back to 17th century which have been tastefully restored preserving the ancient charm, beauty and the original architectural features like the beamed ceilings and the terracotta-tiled floors. Located between the Val d'Orcia and the hills of the Sienese Chianti, the farmhouse is on two floors: the first floor is accessed by an ancient stone staircase and a small open gallery that lets into a spacious dining room with a Tuscan fireplace, three bedrooms and two bathrooms. On the ground floor there is a living room with stone flooring, a fully equipped professional kitchen with dishwasher, fridge, and brick barbecue. On request possibility of cooking courses, wine tastings of the best Sienese wines and typical Tuscan dinners. The farmhouse, furnished with style and elegance, preserves the ancient terracotta flooring and wooden beamed ceilings and is part of a seven hectare estate composed of land and forest, surrounded by a large private garden with swimming pool, sun deck with river sand, and a small pond. Not far from the house are the stables with the owners’ horses and their pastures. Thanks to its superb location the farmhouse is the ideal starting point to visit the Val di Chiana and Val d'Orcia with its wonderful medieval towns such as Cortona, Montepulciano, San Quirico d'Orcia, Pienza, as well as Montalcino and San Gimignano and the beautiful art towns of Siena, Florence and Arezzo. An ideal place for a relaxing holiday, taking long walks in the woods or visiting the most beautiful and striking sites of Tuscany. This is an off-grid accommodation. The farmhouse is almost entirely self-sufficient for its own needs and those of its guests thanks to the installation of a photovoltaic and solar thermal system, as well as rainwater harvesting, which helps to offer guests a relaxing and totally eco-friendly vacation. Additional Location Information Situated in the heart of Tuscany, near the centre of the little town of Sinalunga, it is an ideal spot for exploring the natural and artistic beauties of the two central regions of Italy, Tuscany and Umbria, as it is not far from the highway connecting Perugia and Siena. Both localities can be reached in less than an hour. The A1 motorway exit Valdichiana is a few kilometres away, permitting easy and fast travel in all central Italy. The property uses the railway station of Sinalunga, connected with the more important one of Chiusi. Distances to: * Airports: Firenze 122 Km, Pisa 211 km, Roma 226 Km, Milano 457 Km * Train Station: Sinalunga 7 Km, Chiusi 45 km, Siena 49 Km * Highway: highway exit A1 Valdichiana 13,7 km * Attractions within 100 km: Montepulciano 23 km, Arezzo 34 km, Siena 51 km, Pienza 26 km, San Gimignano 91 km, Montalcino 40 km, Radda in Chianti 61 km, Greve in Chianti 81 km, Cortona 33 km, Perugia 69 Km * Services and shops: Farnetella 1 km, Sinalunga 6,5 km * Beach: Tyrrhenian Sea 136 Km * Access road: paved till the entrance gate Facilities: Pure cotton sateen bed linen Terry cloth towels Use of equipped kitchen Refrigerator Dishwasher Iron Ironing board Toaster Radio/Alarm clock Alarm clock Coffee maker Mosquito curtains Hairdryer Heating Hob with 4 burners Firewood Kettle Wood stove Pets allowed only upon prior request Sunbeds Outdoor barbeque Indoor Barbeque Sun chairs 2 Sun umbrellas Outdoor dining table
  • Three Bedroom Split Level Villa San Gimignano

    Three Bedroom Split Level

    San Gimignano: Villa
    • 3 BDR
    • 2 BA
    • Sleeps 6
    • #208538
    €14 to €364 EUR/night Credit Card
    The villa is one half of a lovely country house in a fantastic panoramic position in the hills close to the wonderful medieval town of San Gimignano. The villa is very prettily furnished in country style with a homely atmosphere and opens onto its’ own secluded garden area with lawn and covered terrace perfect for relaxing and dining al fresco. Steps lead from the garden down to the villas private swimming pool set in the terraced grounds below.
  • Wonderful position atop Chianti Hills !

    Wonderful position atop

    Chiusi: Cottage
    • 1 BDR
    • 1 BA
    • Sleeps 3
    • #13388
    €57 to €86 EUR/night  
    At few minutes driving from the most interesting Etruscanian sites of Tuscany. Pienza, Cetona, Sarteano, Siena, Perugia easy to get by this cottage! All around the cottage there are trees and plants like roses and flowers. No houses near the property.

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