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Pienza Villas

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    Travellers to Pienza are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    44 Matching Rentals in PienzaView all 154 rentals
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Podere Castelletto1 / 51
    (4)Excellent
    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    Villa IL MANDORLO between Pienza and Montepulciano private pool and relax1 / 22
    (1)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    7 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
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    • Private Garden
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    53026, Pienza, Province of Siena
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 13
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    8 Bedrooms, 12 Bathrooms, Sleeps 16 Quick View
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    • Private Outdoor Pool (Unheated)
    • Internet Access
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    • Balcony
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    • Terrace
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    Pet friendly
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    Smoking allowed
    About this property
    Casanova Relais is a wonderful podere dating back to the 1600s, that has painstakingly been restored with a perfect taste. The owners have tastefully created an extremely elegant and comfortable home for modern living with spacious bedrooms, a well equipped kitchen and a beautiful swimming pool....
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    53026, Monticchiello, Pienza
    Holiday Rental House - 8 Bedrooms, 12 Bathrooms, Sleeps 16
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    6 Bedrooms, 10 Bathrooms, Sleeps 22 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • DVD Player
    • Mountain Views
    • Private Outdoor Pool (Heated)
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just out of the fortified town of Monticchiello, in the heart of the Val D'Orcia, one finds this typical Tuscan-Sienese farmhouse surrounded by vineyards, recently restored and refurbished to become a luxury villa. The house is characterized by a central squared unit, whose windows offer a...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 6 Bedrooms, 10 Bathrooms, Sleeps 22
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Outdoor Dining Area
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Careful restoration, ended in May 2015, using original period materials, has maintained the style of the farm and ensured an ancient atmosphere with modern technology. The 4 beautiful and spacious bedrooms have been decorated with elegant colours. Stylish and spacious bathrooms, equipped with...
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    53049, Pienza, Province of Siena
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Grill
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    Pet friendly
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    About this property
    the villa is dated back XI century is semidetached 3 levels tipical medioeval house. Compleltly restored maintened all storical signs: stone walls.stairs as a castle,tipicalTuscany beems in wood . You will be in Unesco's heritage and you will enjoy the quiet , the art the special atmosphere and...
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    53020, Monticchiello, Pienza
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    6 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    • Washer
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This magnificent holiday villa with a heated swimming pool sits on one of the knolls at the foot of Pienza (3km) with a breathtaking 360-degree view over the Val d’Orcia countryside. The villa, 480 sq m, is a tastefully restored stone farmhouse, beautifully furnished in a fine country style, and...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 13
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Secure Parking
    • Grill
    • Wi-Fi
    • Terrace
    • Washer
    • Outdoor Dining Area
    • Balcony
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Arpicella really does offer the best of both worlds! Despite its prime location at just 10 minutes’ walking distance from Pienza, it enjoys the peace and quiet of a beautiful countryside setting with spectacular panoramic views. It is a large, traditionally Tuscan 17th century farmhouse, now...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    8 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    Pet friendly
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    Smoking allowed
    About this property
    Villa Casale Campagna in Siena-Val d\'Orcia, Tuscany is a classic country retreat in the heart of the Tuscan hills. This little gem of a home retains its traditional charm with all the modern conveniences, making it the perfect choice for those seeking an authentic Italian experience. Enter a...
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    Pienza, Province of Siena
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 14
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    Il Tiglio1 / 21
    (1)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
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    Pet friendly
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    Reviewed 6 July 2018
    Location very nice, quiet and peaceful, you can really relax, unfortunately I'm a little disappointed with the property, the house is fine, it was all we needed, a good...
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    53026, Monticchiello, Pienza
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Patio
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa is in the heart of the Val D'Orcia countryside offering luxurious accomodation with a fabulous HEATED swimming pool. The entire country chic house has 6 bedrooms, 6 bathrooms, living rooms with 3 kitchens, dining room, big patio with a stunning view and a special vegetable garden. Spoil...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Wi-Fi
    • DVD Player
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Casale Tranquillo in Siena-Val d'Orcia, Tuscany is an authentic farmhouse dating back to the 19th century that has been transformed into a delightful six-bedroom villa with modern conveniences. From the moment you see the traditional stone structure tucked away in the Tuscan hills, you...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Balcony
    • Grill
    • Private Outdoor Pool (Unheated)
    • Terrace
    • Parking
    • Wi-Fi
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a fantastic 5 bedroom villa near the wonderful town of Montepulciano in Tuscany. Completely surrounded by olive grove and vineyards, it occupies an idyllic setting for guests to enjoy a peaceful and relaxing holiday. Recently restored, it offers a perfect mix of traditional Tuscan...
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    Pienza, Province of Siena
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Mountain Views
    • Grill
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RECEPTIVE STRUCTURE. The splendid countryside of the unmistakable Val d'Orcia, seen on every side of the large green panoramic garden at 472 m above sea level, a swimming pool set in a secluded position coloured by the reddish reflections of the sun setting over the gentle hills adorned with the...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    7 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Washer
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the wonderful Val d'Orcia, the valley of the Siennese clay hills in southern Tuscany, lies Fonte Senesi, surrounded by the landscape which enchanted Giotto, Perugino and Pinturicchio.In spite of its fame, the charm of these sweet hills, crowned by cypress trees and lonely houses has remained...
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    53026, Monticchiello, Pienza
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 12
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The cottage, called Lucignanello, it is an old historical building placed 2km away from Pienza, in the heart of Val d'Orcia. Being our guests you would have the chance to be in an authentic, exclusive, historical and stunning environment. 'Lucignanello' offers an amazing, view onto Val d'Orcia,...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • DVD Player
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description:Villa sits on a hill next to the charming village of Monticchiello overlooking the Val D’Orcia. The views from the property are truly spectacular and make a meal on the patio or a dip in the pool very special. With high-quality vintage furnishings the villa is extremely...
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    53026, Monticchiello, Pienza
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    8 Bedrooms, 8 Bathrooms, Sleeps 15 Quick View
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    • Internet Access
    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    Owner's description:Villa is sublime, set on 6 hectares of beautifully manicured grounds and nestled amongst the fairytale-like Val d’Orcia. The property is in an ideal location, just a few minutes’ drive from Pienza, one of Tuscany’s most beautiful towns. The property also features a state-of the...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 15
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    4 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    • Washer
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    Pet friendly
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    Owner's description:Pool will be open on: 04 May 2018 22:00:00 \r\nPool will be close on: 28 Sep 2018 22:00:00 \r\ninternet connection WIFI. Midweekly cleaning if the entire property is rented (villa+annexe): 4 hours twice a week. The Val d'Orcia stretches to the south of Siena in a landscape at...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 7
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    7 Bedrooms, 8 Bathrooms, Sleeps 13 Quick View
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    • Private Garden
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    Pet friendly
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    Smoking allowed
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    This 800 sq.mts.Villa has been recently restored combining traditional materials as old cotto for the floors and oak beams for the ceilings with vintage furniture and contemporary art works. The insulated large walls and the ventilated roof keep the house naturally cool during hot summer months....
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    53045, Monticchiello, Pienza
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 13
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    7 Bedrooms, 5 Bathrooms, Sleeps 13 Quick View
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    • Central Heating
    • Washer
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    Pet friendly
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    Smoking allowed
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    Owner's description:Main Description : Panoramic position overlooking the Val d'Orcia and the town of Pienza. Ancient stone farmhouse, nowadays beautiful holiday villa, set in a very panoramic position inside the Parco Artistico Naturale of Val d'Orcia. Only 2 km far we find the well-known...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 13
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    6 Bedrooms, 6 Bathrooms, Sleeps 11 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Owner's description:Pool will be open on: 04 May 2018 22:00:00 \r\nPool will be close on: 28 Sep 2018 22:00:00 \r\ninternet connection WIFI. Midweekly cleaning if the entire property is rented (villa+annexe): 4 hours twice a week. The Val d'Orcia stretches to the south of Siena in a landscape at...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 11
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    8 Bedrooms, 9 Bathrooms, Sleeps 16 Quick View
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    Owner's description:VILLAthis property - PIENZA The villa has an ideal location for nature lovers and it is an excellent starting point for visiting the closest art cities of Siena and Montepulciano. Those who prefer to focus on their well-being can visit the nearby spas of Chianciano Terme and...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 16
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    3 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Parking
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    • Housekeeping Included
    • Central Heating
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    53026, Monticchiello, Pienza
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 9
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    7 Bedrooms, 9 Bathrooms, Sleeps 14 Quick View
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    Owner's description:This property - Siena This beautiful independent villa is located in the well-known valle d'Orcia. Monticchiello is the closest town and it rises on a hill surrounded by the countryside near the town of Pienza. From the surrounding country this small village shows its cassero...
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    53026, Monticchiello, Pienza
    Holiday Rental House - 7 Bedrooms, 9 Bathrooms, Sleeps 14
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    7 Bedrooms, 8 Bathrooms, Sleeps 13 Quick View
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    Owner's description:VILLAthis property - Pienza this property is a private property immersed in the Tuscan countryside. It is an excellent choice for a relaxing holiday enjoying privacy with the benefit of a private swimming pool and it is also an ideal location to explore central Italy. this...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 13
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Washer
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    • Wi-Fi
    • Housekeeping Included
    • Central Heating
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    53026, Monticchiello, Pienza
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    9 Bedrooms, 9 Bathrooms, Sleeps 23 Quick View
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    • Grill
    • Private Garden
    • Parking
    • Housekeeping Included
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    53026, Monticchiello, Pienza
    Holiday Rental House - 9 Bedrooms, 9 Bathrooms, Sleeps 23
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    9 Bedrooms, 28 Bathrooms, Sleeps 18 Quick View
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    Owner's description:VILLAthis property -this property this property is an independent villa with private swimming pool, set amid the rolling countryside of Val d'Orcia, south of Siena. Val d'Orcia has been a UNESCO world heritage since 2004. It is a working Estate producing corn, olive oil and DOC...
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    53026, Monticchiello, Pienza
    Holiday Rental House - 9 Bedrooms, 28 Bathrooms, Sleeps 18
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    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Owner's description:VILLAthis property - SARTEANO This villa (170 sq. m) is located in the heart of the Val d'Orcia, a few kilometres from Pienza and Montepulciano. It is surrounded by oak and cypress trees: the ideal location for those who like to enjoy not only the tranquillity of the countryside...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Grill
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    Owner's description:Beautiful stone farmhouse situated in peaceful and panoramic location near the charming medieval town of Pienza, in the heart of the Orcia Valley region. This villa which has been recently restored with all its original details preserved, comprises 3 separate units rented...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    7 Bedrooms, 8 Bathrooms, Sleeps 13 Quick View
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    Owner's description:VILLAthis property - PIENZA AREA This stone farmhouse (440 sq. m) is set in a panoramic position in the heart of Val d'Orcia. It is part of a large farm estate and preserves the typical features of the old country houses. This is a perfect place for those who like to relax in...
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    53026, Monticchiello, Pienza
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 13
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Air Conditioning
    • DVD Player
    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description:Main Description : Beautiful stone farmhouse situated in peaceful and panoramic location near the charming medieval town of Pienza, in the heart of the Orcia Valley region. This villa which has been recently restored with all its original details preserved, comprises 3 separate...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    7 Bedrooms, 5 Bathrooms, Sleeps 13 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description:Panoramic position overlooking the Val d'Orcia and the town of Pienza. Ancient stone farmhouse, nowadays beautiful holiday villa, set in a very panoramic position inside the Parco Artistico Naturale of Val d'Orcia. Only 2 km far we find the well-known Renaissance village of...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 13
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    7 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description:Ancient stone farmhouse, nowadays beautiful holiday villa, set in a very panoramic position inside the Parco Artistico Naturale of Val d'Orcia. Only 2 km far we find the well-known Renaissance village of Pienza, native town of Pope Pio II and declared by the UNESCO a world...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 15
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Owner's description:VILLAthis property - Pienza Nestled between Monticchiello and Montepulciano, this property is an independent villa with private pool based in a large farm that produces milk and various delicious cheeses. Set amid the rolling countryside of Val d'Orcia, south of Siena, this is...
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    53026, Monticchiello, Pienza
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    8 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    Owner's description:Main Description : Imposing farmhouse dating back to the 18th century comprising 2 independent units (rentable only together as a private property). This beautiful 5–hectare estate is situated in quiet and panoramic location, in the heart of the Val d’Orcia region, a short...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 14
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    8 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    Kid friendly
    Smoking allowed
    About this property
    Owner's description:Main Description : Imposing farmhouse dating back to the 18th century comprising 2 independent units (rentable only together as a private property). This beautiful 5–hectare estate is situated in quiet and panoramic location, in the heart of the Val d’Orcia region, a short...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 14
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    8 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
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    Owner's description:VILLAthis property - SIENA The villa, close to Pienza and Montepulciano, sleeps comfortably 16 adults. It has elegantly furnished living areas opening out to the yard for dining 'al fresco', BBQ, stunning views over the valley and its own swimming pool open from the 26th of...
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    53026, Monticchiello, Pienza
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 12
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    Owner's description:Main Description : Beautiful stone farmhouse situated in peaceful and panoramic location near the charming medieval town of Pienza, in the heart of the Orcia Valley region. This villa which has been recently restored with all its original details preserved, comprises 3 separate...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    8 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    Kid friendly
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    About this property
    Owner's description:Imposing farmhouse dating back to the 18th century comprising 2 independent units (rentable only together as a private property). This beautiful 5–hectare estate is situated in quiet and panoramic location, in the heart of the Val d’Orcia region, a short distance away from the...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 14
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    8 Bedrooms, 8 Bathrooms, Sleeps 9 Quick View
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    • Grill
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    • Internet Access
    • Hot Tub
    • Private Indoor Pool
    • Mountain Views
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    http://crazyforitaly.com/property.aspx/61/Pienza_Villa_heated_pool_ Beautiful new villa located in the heart of Tuscany, near the town of Pienza. It is elegant in it's rustic decor. In the spring you are surrounded by hilss of wheat and sunflower fileds. The warm colors and open air rooms provide...
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    1111, Pienza, Province of Siena
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 9
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