Montepulciano Condo Rentals

Looking for the ultimate Montepulciano condo rental? We have 3 condos in Montepulciano resorts. Owner Direct Vacation Rentals offers fabulous condos for rent in Montepulciano and throughout Italy. Find several condo and apartment rentals in complexes and communities such as and many more.

Find a condo downtown or a luxury apartment with a great view away from the hustle and bustle. Clear, concise, easy to read listings, coupled with excellent customer service and great prices are the perfect combination to help you save time and money when planning the perfect getaway and Montepulciano accommodations.

By definition, a condominium or condo is a building or complex of buildings containing a number of individually owned apartments or houses. As an alternative to a Montepulciano hotel, consider renting a condo on your next vacation or holiday. The extra space and freedom will be well worth it.

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3 Apartment and Condo Rentals

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  • Two Bedroom Ground Floor Apartment Montepulciano

    Two Bedroom Ground Floor

    Montepulciano: Apartment
    • 2 BDR
    • 2 BA
    • Sleeps 5
    • #201474
    avg €157 EUR/night Credit Card Pet Friendly
    Fontana della Quercia is a charming apartment in a pretty farmhouse situated on a beautiful estate with unspoilt views of vineyards and olive groves all around. The apartment is extremely tastefully furnished in exquisite Tuscan style and has its own garden area with table and chairs perfect for dining al fresco. In the grounds of the estate is a lovely swimming pool bordered by a sun terrace and lawns. Montepulciano, a famous Tuscan town renowned for its wine, is close by and the rest of Tuscany and Umbria is easily explored from this tranquil location.
  • Overlooking Montepulciano Valley, Countryside, Quiet, Secluded, Big View.

    Overlooking Montepulciano

    Montepulciano: Farmhouse
    • 3 BDR
    • 2 BA
    • Sleeps 6
    • #204536
    avg €103 EUR/night Credit Card Paypal Pet Friendly
    Sleeps six, over 972 square feet. Restored in 1990, it is the result of successive works on the original tower dating back to 17th century. Tucked into the hillside, with perfect views across to Montepulciano, the house is set over two levels. On the ground floor, a lounge with fireplace forms the centre of the house. From here you have access to the three bedrooms: one double, and two twins. One of these has en-suite bathroom with shower. The other bathroom has a bath tub. Wooden stairs lead to the upper floor, where there is a large kitchen/dining room with a fireplace for barbecues. Access to the kitchen is also through a terrace equipped with iron chairs and table. Another terrace, shaded by a pair of old oaks, looks over the valley. Throughout, the house has period furniture from the owner's family. Central heating, and sun loungers in the garden. -------- The property. Farm Capanne di Sopra is located 1.2 kms from the hamlet of Montefollonico, in a quiet setting which enjoys the unmatched skyline of Montepulciano, with its masterpiece temple of San Biagio, Val d’Orcia's hilly border and top of Mount Amiata. The property is situated on a slope at 450 meters of altitude, covering a 5 hectars hilly surface, with an olive grove and a small vineyard, which give an “extravergine” olive oil, and a Chianti Colli Senesi DOCG red wine. The two stone farmhouses of the property -six sleeping places each- have been restored in accordance with Tuscan traditions, and carefully furnished with owner's family pieces. The two houses, although closed one another, are independent and assure absolutely privacy to residents. The houses are fully equipped for six: in the kitchen, bedrooms and bathrooms. Barbecues in the kitchen (wood is available). The houses have: drinkable water from public utility, instant hot water, mobile telephone, washing machines and central heating. Baby cots and high chairs. There are a number of sun chairs and iron made chairs and table to dine outside. A USB key is available for Internet access ( 3G Network). To preserve the character of the site, the owners chose not to build any swimming pool. In any city nearby there is a public swimming pool. Some 400 meters from the paved road, the site remains secluded while accessible only via a private driveway, ensuring that you'll be staying undisturbed, in the midst of olive groves, vineyards and woods. Parking area at the entrance of the property. Historical and cultural sites nearby include Montepulciano, Pienza, Montalcino, Cortona, Chiusi, Monte San Savino, Siena, Arezzo, Perugia and Lake Trasimeno which are all within 75 minutes drive. The thermal spas and bathing at Chianciano, Bagno Vignoni, Bagni San Filippo and Rapolano are no more than half an hour's drive away. There are three swimming pools within 10 kilometers and tennis courts, horseback riding and mountain biking are nearby.
  • Overlooking Montepulciano Valley, Countryside, Quiet, Secluded, Big View.

    Overlooking Montepulciano

    Montepulciano: Farmhouse
    • 3 BDR
    • 2 BA
    • Sleeps 6
    • #204535
    avg €144 EUR/night Credit Card Paypal Pet Friendly
    6 people, about 1405 sf., restored in 1999, enjoys a splendid view towards south and west with large hay for sitting outside. A three entrance ground floor, with french windows to the garden, has a brightly and well equipped kitchen ( gas machine with oven, fridge, fire place-barbecue, washing machine), with store room besides. The kitchen leads into a two room lounge with a Tuscan fire place at one end, furnished with antique pieces of furniture and many sofas and armchairs. A small toilet is available at ground floor. Stone steps take to first floor which has a master bedroom with en-suite bathroom (tub) and splendid view over Montepulciano valley. Other two twin bedrooms share a bathroom with shower. Wrought iron beds, old rustic furniture, small wooden toilet mirrors, doors and in wall- wardrobes have been chosen according Tuscan country tradition. The house is airy and bright all day long. Central heating is available. Panoramic space outside equipped with chaises-longues and iron-made chairs and table. ----- The property. Farm Capanne di Sopra is located 1.2 kms from the hamlet of Montefollonico, in a quiet setting which enjoys the unmatched skyline of Montepulciano, with its masterpiece temple of San Biagio, Val d’Orcia's hilly border and top of Mount Amiata. The property is situated on a slope at 450 meters of altitude, covering a 5 hectars hilly surface, with an olive grove and a small vineyard, which give an “extravergine” olive oil, and a Chianti Colli Senesi DOCG red wine. The two stone farmhouses of the property have been restored in accordance with Tuscan traditions, and carefully furnished with owner's family pieces. The two houses, although closed one another, are independent and assure absolutely privacy to residents. The houses are fully equipped for six: in the kitchen, bedrooms and bathrooms. Barbecues in the kitchen. The houses have: drinkable water from public utility, instant hot water, mobile telephone, washing machines and central heating. Baby cots and high chairs. There are a number of sun chairs and iron made chairs and table to dine outside. A USB key is available for Internet 3G access. To preserve the character of the site, the owners chose not to build any swimming pool. In any city nearby there is a public swimming pool. Some 400 meters from the paved road, the site remains secluded while accessible only via a private driveway, ensuring that you'll be staying undisturbed, in the midst of olive groves, vineyards and woods. Parking area at the entrance of the property. Historical and cultural sites nearby include Montepulciano, Pienza, Montalcino, Cortona, Chiusi, Monte San Savino, Siena, Arezzo, Perugia and Lake Trasimeno which are all within 75 minutes drive. The thermal spas and bathing at Chianciano, Bagno Vignoni, Bagni San Filippo and Rapolano are no more than half an hour's drive away.
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  • Located near San Gimignano (Siena), Tuscany.

    Located near San Gimignano

    Borgo Le Fontanelle: Apartment in a complex
    • 2 BDR
    • 2 BA
    • Sleeps 5
    • #224080
    avg €101 EUR/night Paypal
    Welcome to San Gimignano in Tuscany. A completely restored rural hamlet, is located eight km from the medieval town of San Gimignano. San Gimignano was a stopping point of the “Via Francigena”, the ancient road used by the catholic pilgrims coming from North Europe on their way to Rome. The "Historic Center of San Gimignano" is a UNESCO World Heritage Site. The holiday house is also in the vicinity of Volterra, Siena, Florence, Pisa and is about an hour's drive to the seaside. The Apartment (about 65 sq. Meter) is located on the first floor. It consists of a living room (sofa bed, easy chair, dining table with six chairs and a well equipped kitchen), two double bedrooms and two bathrooms with showers. From the private garden, equipped with a table and six chairs (about 20 sq. Meter), there is a stair (seven steps) to arrive to the apartment entrance. The entire hamlet has been renovated in 2008. In the common area of the hamlet there is an unheated swimming pool (about 14 m x 7 m and 1.4 m deep, open from May 15 until September 15) a bathroom and two showers with hot/cold water. A solarium, a barbecue area with tables and chairs, a laundry room, a fitnessroom and a park surrounded by green nature are all for common use of the guests. A pleasant and healthy place to stay in the summer as well as in the other seasons, Ideal holiday house for vacation in Tuscany. It is located near San Gimignano, a stopping point of the Via Francigena. It is part of a renovated rural hamlet with a swimming pool, surrounded by green nature. Independent heating. Free 2G WiFi is available. No-smoking apartment. No pets. Car is essential. The region.Relaxing in the heart of Tuscany, between Florence and Siena. Ideal for visiting San Gimignano 8 km Colle Val d'Elsa 16 km Volterra 18 km Poggibonsi 19 km (train station) Area of Chianti Classico : 20 km Certaldo 23 km the Boccaccio town Castle of Monteriggioni 36 km Siena 40 km Cecina (seaside town) 65 km Florence 66 km (airport and main train station) Pisa 80 km (airport) Ideal for hiking on the Via Francigena. Shops, supermarkets and restaurants can be found in Castel San Gimignano (4 km) or in San Gimignano (8 km)
  • BEAUTIFUL HILLTOP 2 Story Farmhouse APARTMENT in the Heart of Tuscany

    BEAUTIFUL HILLTOP 2 Story

    San Gimignano: Apartment
    • 1 BDR
    • 1 BA
    • Sleeps 5
    • #119703
    avg $98 USD/night Credit Card Paypal Pet Friendly
    THE HEART OF TUSCANY WITH STUNNING SURROUNDINGS,PERCHED ON TOP OF A HILL OVERLOOKING THE BEAUTIFUL ROLLING HILLS BETWEEN SAN GIMIGNANO AND VOLTERRA. You can easily visit Florence,Siena,Pisa,Chianti,Sea,Monteriggioni. 2 spacious rooms (bedroom,living room,kitchen w/dining area,fridge,stove,bathroom with shower),Newly renovated,TV,shared pool, BBQ area,garden private area. NEARBY: horse riding, walking, cycling, golf, tennis, beaches of Cecina and Thyrrenian Sea,Chianti Region,Many Vineyards,Restaurants/Bar,Old Village(500meters). Cooking classes,Wellness,Siena Bus Tours/Hot Air ballooning CHARACTER: Apartment is a two story portion of a completely renovated mid 1800's Tuscan farmhouse. It has been born again to great detail and respect of the original country-style, and is ideal to those who love nature and dream of a relaxing holiday far away from the stressful bustle of everyday. This apartment / villa is in a perfect position to rent / let out on a daily/weekly or monthly basis. SIZE: 2 spacious rooms (bedroom, living room, kitchen w/dining area, fridge, stove, bathroom with shower), sleeps comfortably 4 with possibility of 5th person added. FEATURES: Newly renovated, TV, shared swimming pool, barbecue area, garden private area MINIMUM STAY: 3 nights, ADVANTAGES: Gorgeous views, competitive prices, recent Renovation with nice grounds, centrally located for visiting Tuscany and the rest of country, number of great restaurants nearby, possibility to purchase olive oil, cheese, wine tasting within walking distance.
  • Apartment with Private Garden in Ancient Farmhouse

    Apartment with Private

    Casole d'Elsa: Apartment
    • 2 BDR
    • 1 BA
    • Sleeps 4
    • #205729
    avg €60 EUR/night Paypal Pet Friendly
    The apartment is part of a farmhouse in a hill top position in the wonderful countryside west of Siena. It lies 12 KM far from Casole d’Elsa and 9 from Radicondoli, typical medieval villages still retaining their charm and original character. Our property is a perfect jump off point to explore the enchanting Tuscany, including seaside towns. City of art such as Siena, Florence, San Gimignano, Volterra, Monteriggioni, Massa Marittima are easily accessible on good roads. The house was built over an Etruscan site, that was inhabited since then. Also the nature lovers will enjoy the river reserves and wildlife sanctuaries of the area. Culinary specialities from land and sea await your discovery. The famous wine region “Chianti” is only 25 KM away. The apartment has its own patio and garden, from which our guests can enjoy the panoramic views and peace. There are various rivers in the area (Merse, Farma, Pavone and Cecina) with clean waters and good streams. Thermal baths are in Petriolo, 30 KM from our property, where hot water flows in the river Farma, offering a hot-cold swimming option. And in Rapolano Terme (40 KM far). Nice public pools are also in the town of Colle di Val d'Elsa and casole d'Elsa.
  • Two Bedroom Apartment with Large Balcony on Gorgeous Estate with Swimming Pool

    Two Bedroom Apartment with

    San Gimignano: Apartment
    • 2 BDR
    • 2 BA
    • Sleeps 5
    • #202201
    avg €109 EUR/night Credit Card Pet Friendly Star Rating
    <b>Local charges noted below are paid on arrival and are NOT included in the quote provided by Owner Direct - Heating on consumption Accommodation tax from 1st March to 31st October, Euro 1,50 per person per night (max 5 nights) children under 12 years free of charge</b> A winding avenue of cypress trees leads to the apartment on the estate. Situated in a fantastic elevated position above San Gimignano, there are lovely views of the countryside and the medieval town across the valley. The unit is a part of a restored farmhouse, is a bright and comfortably furnished apartment with a great highlight of a large private balcony (44 sqm) shaded by a pergola, where you can relax and enjoy the marvellous panorama. A short walk through the grounds lead to the beautiful swimming pool (14m x 7m) which looks out across vineyards and olive groves to the distant hills. The pool is furnished with sunbeds and sun umbrellas and there is a handy changing room with shower. There is a washing machine and barbecues for guest use and farm produced wine and olive oil are available. Guests are free to wander the extensive estate where there are lovely country walks and fabulous views all around. The property is only 4.5 kms from San Gimignano. Known as ‘The City of Towers’. It is a fascinating place to explore with many craft shops, local art galleries and historic monuments, as well as an excellent selection of restaurants. Being in central Tuscany its a great base from which to explore this beautiful region, with Florence and Siena being within easy driving distance.
  • Tuscan Living at its Best in this Exclusive Family-Owned Wine Farm near Siena

    Tuscan Living at its Best

    Buonconvento: Farmhouse
    • 4 BDR
    • 2 BA
    • Sleeps 8
    • #74721
    avg €320 EUR/night Credit Card Paypal Pet Friendly
    Enjoy the quiet and serene surroundings that only this area of Tuscany can offer: lovely views and sunsets, and long nature walks. Living space is on the first floor above ground, since the original layout was made to accommodate the animals on the ground floor, where still today, we have the stalls used now for storage. It is a very pleasant car drive of approx. 30 kilometers to Siena and 10 kilometers away from Montalcino. Lovely enjoyable and easy drive day trips to the neighboring towns and monasteries such as Montalcino, Pienza or the Abbey of Monte Oliveto Maggiore. Tennis courts and horseback riding nearby. Mountain bikes for rent as well. Wifi in the house for your use. Large celling fans are in every bedroom with mosquito screens .
  • Delightful and Romantic Renovated Hayloft Now a Comfortable 2 Level Farmhouse

    Delightful and Romantic

    Buonconvento: Farmhouse
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #208473
    avg €175 EUR/night Credit Card Paypal
    This cottage is the latest addition to the small antique hamlet called Borgo Castelrotto. It is a converted hayloft that is now a charming and romantic getaway. The upstairs bedroom that overlooks the beautiful surrounding countryside is a loft style with its own bathroom and air-conditioning. Downstairs there is a large living room that leads into the open kitchen with all modern amenities. There is another bedroom, with air-conditiong, and an ensuite bathroom with shower. There is a restored brick and stone fireplace in the cozy living that adds to the unique atmosphere of this farmhouse. Enjoy incredible tranquillity and sunsets by sitting in your private garden or by the pool that overlooks the olive orchard and the Ombrone river valley. The infamous bike path "Eroica" is just behind our property and easily doable for all ages. Biking, walking, tennis and horseback riding, hot air ballooning rides are all within a very short distance.
  • Exclusive Tuscan Living in this Family-Owned Wine Estate in Magical Val D'orcia

    Exclusive Tuscan Living in

    Buonconvento: Farmhouse
    • 4 BDR
    • 2 BA
    • Sleeps 8
    • #202562
    avg €320 EUR/night Credit Card Paypal Pet Friendly Star Rating
    Enjoy the quiet and serene surroundings, lovely views of the town of Montalcino in the distance, the sunsets, and long nature walks. Living space is on the first floor above ground, since the original layout was made to accommodate the animals on the ground floor, where still today, we have the stalls used for storage. It is a very pleasant car drive of approx. 30 kilometers to Siena and 10 kilometers away from Montalcino. Lovely day trips to the neighboring towns and monasteries such as Montalcino, Pienza or the Abbey of Monte Oliveto Maggiore, San Galgano or even the beach on the Maremma coast. Tennis courts and horseback riding nearby. Mountain bikes for rent as well. Wifi in the entire property for your use and free of charge. Large ceiling fans in every bedroom.
  • Solaio Self Catering Apartment

    Solaio Self Catering

    Gaiole in Chianti: Villa Vistarenni: Apartment in a villa
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #40563
    avg €208 EUR/night Credit Card
    This apartment on the second floor of the Villa is accessible through two flights of old stairs. From there, you can admire the enchanting view of the Chianti hills. The unchangeable charm of nature will sooth and uplift you. The flat is furnished with old family pieces that make it very cozy and charming. The two bedrooms are large and comfortable, with old terracotta floors, ceilings with exposed beams and an old terracotta stove and a kitchen which accommodates four people.
  • Impressive Apartment in La Villa of 16th century

    Impressive Apartment in La

    Gaiole in Chianti: Villa Vistarenni: Apartment in a villa
    • 7 BDR
    • 6 BA
    • Sleeps 8
    • #39947
    avg €1,350 EUR/night Credit Card
    The Villa suits those who want to spend some time in the countryside and still want to enjoy the beauties and comforts on which the aristocratic Tuscan families modeled their houses. The richness of details and the period furniture of the rooms will give you a sense of belonging, as if your life were linked, were it for a short time, to the real nature of this beautiful house. It preserves the original historical architecture and the antique atmosphere of the people who lived here in the past. The frescoes, the decorated ceiling and the golden bureaus, painted beams, restored antiques and precious draperies, paintings and ancient prints are a perfect mix of antique furniture and objects of design: they all render this place elegant and tidy but at the same time, extremely delicate. 6 double rooms with en-suite bathrooms, 1 communicating single room,1 single room, dining room, living room on the first floor with fireplace, living room with french open door onto the garden with beautiful view over the Chianti hills, kitchen, library. 750 square metres, first and ground floor. Free Wi Fi During your stay you can apply for a cook and you can have a maid three hours per day. We can offer you first shopping, baby sitter, transfer from and to the airports, wine tasting and tour of the ancient cellar. Exclusive use of swimming pool and tennis court
  • Bellina Self Catering Apartment

    Bellina Self Catering

    Gaiole in Chianti: Villa Vistarenni: Apartment in a villa
    • 3 BDR
    • 2 BA
    • Sleeps 6
    • #40562
    avg €230 EUR/night Credit Card
    Two flights of old stairs lead to the top floor of the Villa. From the three comfortable bedrooms, two of which are communicating and one especially made for children, you can admire the splendid view of the small village of Radda in Chianti perched on the top of the hill. The terracotta tiled floor, the coffered ceiling and the murals from the 19th century make it unique and wherever you look at you will perceive a fragment of history.
  • An Exclusive Farm-House with a wonderfull view of San Gimignano.

    An Exclusive Farm-House

    San Gimignano: Il Coltro: Apartment in a villa
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #202971
    avg €167 EUR/night Pet Friendly Star Rating
    San Gimignano is a small walled medieval hill town in the province of Siena, Tuscany, north-central Italy. It is mainly famous for its medieval architecture, especially its towers, which may be seen from several kilometers outside the town. The town also is known for the white wine, Vernaccia di San Gimignano, grown in the area. San Gimignano was founded as a small village in the 3rd century BC by the Etruscans. In the Middle Ages and Renaissance era. It was a stopping point for Catholic pilgrims on their way to Rome and the Vatican, as it sits on the medieval Via Francigena. The city's development also was improved by the trade of agricultural products from the fertile neighboring hills. There are many churches in the town. The two main ones are the Collegiata, formerly a cathedral, and Sant'Agostino, housing a wide representation of artworks from some of the main Italian renaissance artists. The Communal Palace, once seat of the podestà, is currently home of the town gallery, with works by Pinturicchio, Benozzo Gozzoli, Filippino Lippi, Domenico di Michelino, Pier Francesco Fiorentino and others. Tea with Mussolini, a 1999 drama, about the plight of English and American expatriate women in Italy during World War II, was filmed in part at San Gimignano. The the main actresses Maggie Smith, Judi Dench, Lily Tomlin stayed for the duration of the shoot at this property.
  • An Exclusive Farm-House With a Wonderful View on San Gimignano

    An Exclusive Farm-House

    San Gimignano: Il Coltro: Apartment in a villa
    • 2 BDR
    • 1 BA
    • Sleeps 4
    • #202967
    avg €158 EUR/night Pet Friendly
    San Gimignano is a small walled medieval hill town in the province of Siena, Tuscany, north-central Italy. It is mainly famous for its medieval architecture, especially its towers, which may be seen from several kilometres outside the town. The town also is known for the white wine, Vernaccia di San Gimignano, grown in the area. San Gimignano was founded as a small village in the 3rd century BC by the Etruscans. In the Middle Ages and Renaissance era, it was a stopping point for Catholic pilgrims on their way to Rome and the Vatican, as it sits on the medieval Via Francigena. The city's development also was improved by the trade of agricultural products from the fertile neighbouring hills. There are many churches in the town: the two main ones are the Collegiata, formerly a cathedral, and Sant'Agostino, housing a wide representation of artworks from some of the main Italian renaissance artists. The Communal Palace, once seat of the podestà, is currently home of the town gallery, with works by Pinturicchio, Benozzo Gozzoli, Filippino Lippi, Domenico di Michelino, Pier Francesco Fiorentino and others. Tea with Mussolini, a 1999 drama about the plight of English and American expatriate women in Italy during World War II, was filmed in part at San Gimignano. The the main actresses Maggie Smith, Judi Dench, Lily Tomlin stayed for the duration of the shoot at this property.
  • An Exclusive Farm-House With a Wonderful View on San Gimignano

    An Exclusive Farm-House

    San Gimignano: Il Coltro: Apartment in a villa
    • 2 BDR
    • 1 BA
    • Sleeps 4
    • #202964
    avg €145 EUR/night Pet Friendly
    San Gimignano is a small walled medieval hill town in the province of Siena, Tuscany, north-central Italy. It is mainly famous for its medieval architecture, especially its towers, which may be seen from several kilometres outside the town. The town also is known for the white wine, Vernaccia di San Gimignano, grown in the area. San Gimignano was founded as a small village in the 3rd century BC by the Etruscans. In the Middle Ages and Renaissance era, it was a stopping point for Catholic pilgrims on their way to Rome and the Vatican, as it sits on the medieval Via Francigena. The city's development also was improved by the trade of agricultural products from the fertile neighbouring hills. There are many churches in the town: the two main ones are the Collegiata, formerly a cathedral, and Sant'Agostino, housing a wide representation of artworks from some of the main Italian renaissance artists. The Communal Palace, once seat of the podestà, is currently home of the town gallery, with works by Pinturicchio, Benozzo Gozzoli, Filippino Lippi, Domenico di Michelino, Pier Francesco Fiorentino and others. Tea with Mussolini, a 1999 drama about the plight of English and American expatriate women in Italy during World War II, was filmed in part at San Gimignano. The the main actresses Maggie Smith, Judi Dench, Lily Tomlin stayed for the duration of the shoot at this property.
  • An Exclusive Farm-House With a Wonderful View on San Gimignano

    An Exclusive Farm-House

    San Gimignano: Il Coltro: Apartment in a complex
    • 2 BDR
    • 1 BA
    • Sleeps 4
    • #202963
    avg €145 EUR/night Pet Friendly
    San Gimignano is a small walled medieval hill town in the province of Siena, Tuscany, north-central Italy. It is mainly famous for its medieval architecture, especially its towers, which may be seen from several kilometres outside the town. The town also is known for the white wine, Vernaccia di San Gimignano, grown in the area. San Gimignano was founded as a small village in the 3rd century BC by the Etruscans. In the Middle Ages and Renaissance era, it was a stopping point for Catholic pilgrims on their way to Rome and the Vatican, as it sits on the medieval Via Francigena. The city's development also was improved by the trade of agricultural products from the fertile neighbouring hills. There are many churches in the town: the two main ones are the Collegiata, formerly a cathedral, and Sant'Agostino, housing a wide representation of artworks from some of the main Italian renaissance artists. The Communal Palace, once seat of the podestà, is currently home of the town gallery, with works by Pinturicchio, Benozzo Gozzoli, Filippino Lippi, Domenico di Michelino, Pier Francesco Fiorentino and others. Tea with Mussolini, a 1999 drama about the plight of English and American expatriate women in Italy during World War II, was filmed in part at San Gimignano. The the main actresses Maggie Smith, Judi Dench, Lily Tomlin stayed for the duration of the shoot at this property.
  • An Exclusive Farm-House With a Wonderful View on San Gimignano

    An Exclusive Farm-House

    San Gimignano: Il Coltro: Apartment in a villa
    • 1 BDR
    • 1 BA
    • Sleeps 4
    • #202936
    avg £120 GBP/night Pet Friendly
    San Gimignano is a small walled medieval hill town in the province of Siena, Tuscany, north-central Italy. It is mainly famous for its medieval architecture, especially its towers, which may be seen from several kilometres outside the town. The town also is known for the white wine, Vernaccia di San Gimignano, grown in the area. San Gimignano was founded as a small village in the 3rd century BC by the Etruscans. In the Middle Ages and Renaissance era, it was a stopping point for Catholic pilgrims on their way to Rome and the Vatican, as it sits on the medieval Via Francigena. The city's development also was improved by the trade of agricultural products from the fertile neighbouring hills. There are many churches in the town: the two main ones are the Collegiata, formerly a cathedral, and Sant'Agostino, housing a wide representation of artworks from some of the main Italian renaissance artists. The Communal Palace, once seat of the podestà, is currently home of the town gallery, with works by Pinturicchio, Benozzo Gozzoli, Filippino Lippi, Domenico di Michelino, Pier Francesco Fiorentino and others. Tea with Mussolini, a 1999 drama about the plight of English and American expatriate women in Italy during World War II, was filmed in part at San Gimignano. The the main actresses Maggie Smith, Judi Dench, Lily Tomlin stayed for the duration of the shoot at this property.
  • An Exclusive Farm-House With a Wonderful View on San Gimignano

    An Exclusive Farm-House

    San Gimignano: Il Coltro: Apartment in a complex
    • 1 BDR
    • 1 BA
    • Sleeps 4
    • #202925
    avg €117 EUR/night Pet Friendly
    San Gimignano is a small walled medieval hill town in the province of Siena, Tuscany, north-central Italy. It is mainly famous for its medieval architecture, especially its towers, which may be seen from several kilometres outside the town. The town also is known for the white wine, Vernaccia di San Gimignano, grown in the area. San Gimignano was founded as a small village in the 3rd century BC by the Etruscans. In the Middle Ages and Renaissance era, it was a stopping point for Catholic pilgrims on their way to Rome and the Vatican, as it sits on the medieval Via Francigena. The city's development also was improved by the trade of agricultural products from the fertile neighbouring hills. There are many churches in the town: the two main ones are the Collegiata, formerly a cathedral, and Sant'Agostino, housing a wide representation of artworks from some of the main Italian renaissance artists. The Communal Palace, once seat of the podestà, is currently home of the town gallery, with works by Pinturicchio, Benozzo Gozzoli, Filippino Lippi, Domenico di Michelino, Pier Francesco Fiorentino and others. Tea with Mussolini, a 1999 drama about the plight of English and American expatriate women in Italy during World War II, was filmed in part at San Gimignano. The the main actresses Maggie Smith, Judi Dench, Lily Tomlin stayed for the duration of the shoot at this property.
  • Secluded on the top of a hill with no neighbours

    Secluded on the top of a

    Siena: Apartment in a villa
    • 2 BDR
    • 1 BA
    • Sleeps 6
    • #58986
    avg €156 EUR/night Credit Card Paypal Pet Friendly
    Secluded on the top of a hill with no neighbours. The panorama is incredibly beautiful. You can see the Castle of Celsa, Siena, the Chianti hills, and the Apennines.
  • Tranquillity Found.  Authentic Tuscan Farmhouse Btwn Val D'orcia & Val Di Chiana

    Tranquillity Found

    Sarteano: Farmhouse
    • 4 BDR
    • 4 BA
    • Sleeps 8
    • #212416
    avg $786 USD/night Paypal
    A World away... Or at least that's how it seems. Located just 15 convenient minutes from the A1 autostrada equidistant from Rome and Florence, this recently restored farmhouse is close to everything: the village is down the hill, the shopping center and the train station are all a few minutes away by car, and scores of enchanting Tuscan villages are an easy drive away. But the most magical thing about its location is its seeming isolation. Up here on the hill, civilization as we know it lies far, far away, the air is cooler and cleaner, the panoramas stretch out at your feet for miles, the sounds and smells and colors, more vibrant. Whether you're lounging by the pool, happily slicing and dicing away for a luncheon party, meditating in the deliciously cool and peaceful woods, or working up a sweat hiking into town for provisions, you'll be surrounded by genuine Tuscan beauty. The property (Main house and Guest Tower) easily accommodates 8 people in 4 bedrooms, each with its own en suite bath. We wanted to preserve as many of the original building materials as possible and were very rigorous in incorporating local building traditions and techniques in the restoration, using native stone, marble and color pigments throughout the house. Furnished with a sophisticated mix of European antiques and modern upholstered pieces, the house is stylish yet down-to-earth. The main house consists of 3 bedrooms and 3 baths, a large living room, dining room, a reading/TV room, laundry, and an enormous gourmet kitchen. The tower is affectionately known as 'the honeymoon suite." Set apart, it is a 2 story structure with a downstairs sitting room and bath, and a lovely bedroom upstairs. The views from the tower are splendid and it is, indeed, a very romantic spot. The garden, the fields and the woods are what really make the property magical. Created out of a jungle of weeds, shrubs, and brambles, the garden pays homage to the original olive terraces that were discovered during the restoration process. The front lawn is surrounded by lavender hedges and flowering shrubs and is shaded by cypress and oak trees. The kitchen herb garden provides all the thyme, sage, and rosemary you could possibly use for any culinary adventure. The pool was designed to fit inside the existing measurements of one of these cascading agricultural terraces. Resembling an enormous water trough, it fits seamlessly into the landscape and is completely hidden from view. Only the sound of its delightful waterfall gives away its location. Outside this inner precinct lie the agricultural elements: fields of olive trees, nut trees, remnants of plum hedges and allees of cherry and apple trees. And if you follow the old cart path along the 'serpentine' wall, you descend into the wood. Here you enter Etruria...Lost and found. The house 2 King-bedded Rooms 1 Twin-bedded Room Each bedroom has its own en-suite bathroom. (3) Laundry Room Enormous Kitchen Dining Room Living Room with Fireplace Library/TV Room On the ground level While they are several rooms on the level, only the Games Room is available to guests. Games Room with Foosball Table, Drum Kit, Xbox, etc. The Tower Sitting Room Bath Room Large King-bedded Room with Panoramic View
  • Alone on a Hill at the doors of Siena

    Alone on a Hill at the

    Siena: Apartment in a villa
    • 1 BDR
    • 1 BA
    • Sleeps 2
    • #58274
    avg €77 EUR/night Credit Card Paypal Pet Friendly
    Immersed in the woodlands of the natural park at the doors of Siena, provides the perfect retreat hidden in the heart of oak and chestnut trees and flocks of sheep. The infinite panoramic view includes the towers of Siena, the castle of Celsa and the sloping hills of the Chianti region. The villa offers a swimming pool, wooden sundeck, summer kitchen, and BBQ for candle light evenings.-one cosy studio, ideal for a young couple. Lovingly decorated with Mediterranean warm colours.
  • Charming Chianti Home, Beautiful Views ~ Exquisite Privacy ~ Serene Setting

    Charming Chianti Home

    Castelnuovo Berardenga: Farmhouse
    • 4 BDR
    • 3 BA
    • Sleeps 6
    • #206025
    avg €712 EUR/night Credit Card Paypal Pet Friendly
    A superior-styled vacation home in best area of Tuscany's Chianti region. Easy access and close proximity to Tuscany's finest restaurants make this a perfect choice for your vacation home near Siena and Florence. Recently renovated with all modern conveniences, this 1500's Stone Farmhouse is situated perfectly in the middle of Olive Groves and rolling Chianti Classico Vineyards. U.S. Owner resides in Tuscany, for your travel and touring guidance. Stay in this authentic antique-filled Tuscan Farmhouse behind gates up a long drive within walking distance of small villages of Villa-a-Sesta and San Gusme, restaurants and wine-tasting. A professionally-equipped kitchen and large outdoor living and dining spaces are just two of the premiere features of the property. Dreamliner Views overlooking vineyards and groves, the Chianti valleys, to the distant mountains of the Maremma. The main (middle) floor consists of an updated cook's kitchen, dining salon, living room, powder room, our own 'piazza' and rambling view terraces with fireplace and BBQ. A tended kitchen garden full of herbs, greens and seasonable vegetables, with almond, apricot, fig, and berries only an arm's length away for those yearning to be Tuscan chefs. The 'Vineyard Suite': upper two rooms with en-suite bathroom. Double room along with Single room, private entrance, view terraces, bathroom with jacuzzi-tub+shower. There is a cozy reading nook / window-seat in the double room. The 'Garden Suite': ground floor, two adjoining rooms with large en-suite travertine bathroom. This suite consists of a carved chestnut-wood 17th c. Double room, private entrance with view terrace, a French-Empire single sitting room, travertine Bathroom, antique claw-foot iron tub and large walk-in shower room. The entire property is thoughtfully furnished with 18-19c Italian and French antiques, sculpture, Italian ceramics. Italian bed linens and towels are provided. Wireless internet throughout. There are bicycles for exploring the easy rolling lanes, plenty of local wine and oil, and various in-season festivals and markets. The main dining terrace offers a pergola-covered travertine table with a large BBQ fireplace and seasonal lounge. All windows are screened, sleeping rooms offer individually-controlled air conditioning. AL fresco dining will accommodate up to 12 guests for your special occasions. Plan a home-catered meal on the main terrace for your ultimate Tuscan experience. The estate is minutes from the village of Castelnuovo Berardenga and is within close walking or biking proximity to San Gusme and Villa-a-Sesta, and Gaiole-in-Chianti. Florence is about an hour+,Rome just about 2+ hours. Siena is 20 minutes away. Reached easily by car are towns such as Montalcino, Arezzo, Greve, Cortona, or Castellina-in-Chianti. Tuscan beaches or fishing villages of the Cinque Terra are 2 to 4 hours away.

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