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Holiday Homes in Province of Siena

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    All 4,834 Rentals in Province of Siena
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    Elegant 2 bedroom apt. in historic Siena residence1 / 18
    (32)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Chianti Cashmere Vacation Rentals, Rural Tuscany1 / 40
    (14)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Agriturismo Podere San Giusto1 / 10
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    2 Bedroom Stone Cottage Rental in Chianti Countryside1 / 19
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Mountain Views
    • Cable/satellite TV
    • Grill
    • Washer
    • Hot Tub
    • Central Heating
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 November 2017
    What a lovely place to spend a week, the house has everything that you could need. It was clean. To look around day after day was so very pleasant. It is central, with easy day...
    Reviewed 12 July 2017
    Casanuova di Pietrafitta lovely cottage worked very well for us as a base to explore the beautiful Tuscany region. Day after day of exploring nearby villages when we came back...
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    About this property
    Farmhouse in the heart of Chiantishire at 3 kms minutes distance from the historical township of Castellina in Chianti. 23 kms from Siena and 37 kms from Florence. The villa is set at an altitude of 600 meters. We are surrounded by vineyards and oak woods a perfect place to run away from busy city...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Elegant Tuscan Villa with Spa1 / 35
    (8)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • DVD Player
    • Central Heating
    • Private Indoor Pool
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 February 2018
    It was a prefect stay for the holidays. An absolutely charming and comfortable Villa close to everything we wanted to see, Thank you to Paul our wonderful host. We truly enjoyed...
    Reviewed 6 April 2017
    For those looking for that perfect, tiny, authentic village in Tuscany, Belfort is your place. If you are looking for a spectacular, unique and luxuriously appointed Italian...
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    About this property
    Set in the heart of Tuscany this spacious, detached, hilltop villa has 180° views from a grand terrace and is close to Siena, the beach and all the other important sights. Enjoy fantastic indoor and outdoor spaces. Every room has a view of Tuscany as it unfolds beneath you. Finely decorated with...
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    53030, Radicondoli, Province of Siena
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Housekeeping Included
    • Washer
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Guesthouse is a renowned former residence of an aristocratic Senese family. a short walk from t the Piazza del Campo and next to the main bus.station (Piazza Gramsci) Our Apartments aim to offer a valid alternative to anyone who wants to live their Senese experience with total independence. We...
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    53100, Siena, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Poggio Senese - Pianello mq1101 / 37
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 June 2015
    Our apartment was clean and very well stocked in the kitchen area, including having a dishwasher. The bedroom was large, airy and very comfortable with stunning views down the...
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    53049, Montefollonico, Torrita di Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Attico con altana: incanto e relax tra le bellezze di Siena1 / 22
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    As part of our trip to Tuscany, a group of 4 (2 couples) stayed at Attico con altana in mid June 2018. I chose Attico con altana on the basis of its location right in the heart...
    Reviewed 25 September 2017
    This was a perfect place to stay in Seina. Everything was as described or better. The owner met us at street level upon arrival, so we knew we at the correct address. She...
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    53100, Siena, Province of Siena
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Casa Gelsomino, ground floor, 2 bedrooms, private garden and shared pool1 / 32
    (35)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Central Heating
    • Parking
    • Private Garden
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 October 2017
    Situated in the heart of Tuscany, this property has exceeded our expectations. Lovely hosts, beautiful house surrounded by astonishing views. A property with a nice history...
    Reviewed 24 September 2016
    We loved our stay at castle San Gimiginano. A great place to relax and also travel around parts of Tuscany . Very clean and comfortable accommodation with great views. We would...
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    About this property
    The apartment is located in the hamlet of Castel San Gimignano, very near to the best famous cities as Siena, Firenze, San Gimignano, Volterra and the sea is reachable in less than an hour by car. You can also start from here for a relaxing walk or ride through the olive groves and the surrounding...
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    53030, Castel San Gimignano, San Gimignano
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    La Casa di Alice - Montalcino1 / 18
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Central Heating
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 October 2017
    This home is beautiful, very clean, modern amenities, quiet, spacious yet cozy .... I can go on and on about how wonderful it was. The view from our window was spectacular...
    Reviewed 23 September 2017
    Beautifully decorated home and amazing views of the Tuscan countryside. Castelnuovo dellAbate is about 30 min. drive from Montalcino. Very quiet and peaceful. We did day trips...
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    53024, Castelnuovo dell'Abate, Montalcino
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Rocca dei Monaci1 / 11
    (10)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Parking
    • Outdoor Dining Area
    • Internet Access
    • Cable/satellite TV
    • Private Garden
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53035, Monteriggioni, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Tegline Chianti Tuscan accomodation with pond1 / 70
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Terrace
    • Private Garden
    • Secure Parking
    • Washer
    • Grill
    • Balcony
    • Central Heating
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 April 2018
    We came in a group of 3 and stayed at Tegline for 10 nights in late sepetember 2017. And we had no regrets! our experience was absolutely a satisfactory and memorable one! At...
    Reviewed 3 March 2018
    We were looking for an idyllic and above all a quiet place in Tuscany. And that was what we found!It was really great.Giovanni and Simonetta, our hosts were SO...
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    About this property
    Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce Chianti Classico wine and extra virgin olive oil organic. We restored the farmhouse of the 15th century and Giovanni has personally followed all the works to preserve the history of...
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    VILLA Le Corolline1 / 30
    (15)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Parking
    • Washer
    • Grill
    • Air Conditioning
    • Outdoor Dining Area
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 May 2018
    Great, relaxing retreat! Wished we could have stayed longer than two nights. Roberto is a gracious host. Already planning to make it back here on our next trip to Tuscany.
    Reviewed 7 March 2018
    We will always remember our 3 week stay in Roberto's family farm house. We used it as a base to travel Tuscany and Umbria. Beautiful setting in the family's olive grove in a...
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    53045, Montepulciano, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    La Senesina , enchanting apartment near Siena1 / 27
    (8)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed 6 July 2017
    How should we even begin? We rented this glorious little two bedroom apartment in a converted 12 century convent for 7 weeks. It was perfect for us. This is somewhat hard to...
    Reviewed 6 June 2017
    As Americans traveling abroad, we have two main criteria when choosing a property:1. Helpfulness, attentiveness of the host2. Quality of the propertyAndrea and Barbara’s...
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    About this property
    “La Senesina” is an enchanting apartment immersed in the exquisitely beautiful Tuscan countryside, just 4 km from Siena, 8 km from Monteriggioni, and approximately 5 km from the raccordo autostradale Siena/Firenze (Siena/Florence highway.) Recently restored apartment situated in an historic 16th...
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    53011, Siena, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Balz Tuscan farmholiday Chianti  with pond1 / 67
    (6)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Central Heating
    • Terrace
    • Washer
    • Private Garden
    • Secure Parking
    • Balcony
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 February 2018
    This is a unique, authentic country house in Chianti that is worth experiencing! Simonetta and Giovanni are interesting, warm, sweet and kind and eager to assist in everything...
    Reviewed 30 March 2017
    Tegline is a wonderful place in Tuscany, perfectly equipped and arranged in a charming traditional tuscan style. The casale is consisting of three apartments - they are all...
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    About this property
    Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce Chianti Classico wine and extra virgin olive oil organic.We restored the farmhouse of the 15th century and Giovanni has personally followed all the works to preserve the history of...
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    TuscanFlat1 / 18
    (15)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Washer
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Siena and Tuscan Flat was our third stop of four in the country. The view was, as stated before practically aerial and almost magical. Hearing the cathedral bells chime and the...
    Reviewed 30 May 2018
    Having just come back from 5 days in Siena followed by 5 days in Florence, Siena ticked all the boxes. The city is just beautiful and made even better by the almost aerial view...
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    About this property
    This very stylish 430-square-foot apartment a few minutes walk from Piazza del Campo. You will not need anymore to walk up 66 steps to access this apartment,because now there is a new elevator to lift you on two amazing terraces and their spectacular views. The main living space here is a large,...
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    53100, Siena, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Minnie's Cottage in Tuscany, casa tua a Montalcino1 / 20
    (13)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
    • Parking
    • Wi-Fi
    • Terrace
    • Outdoor Dining Area
    • Washer
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2015
    I bumped into this lovely cottage few months ago while I was searching for a relaxing comfy place right in the heart of Montalcino to spend few days away from everything but...
    Reviewed 22 June 2015
    A charming cottage straight out of a Frederico Fellini movie, in an idyllic setting. It was like having our own Tuscan summer house, complete with the rustic kitchen table, the...
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    53024, Sant'Angelo in Colle, Montalcino
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Casale in antico Mulino nelle colline del Chianti1 / 22
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Garden
    • Grill
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    We enjoyed our stay in Mulino nelle colline del Chianti largely due to our lovely hosts Reffaela and Roberto.They were warm, welcoming and offered plenty of recommendations for...
    Reviewed 26 June 2017
    Wonderfully restored thousand years old mill with great pool and very accommodating hosts. Short distance from Siena and other treasures of Toscany, well worth to stay.
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    53035, Monteriggioni, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Traditional Tuscan-style country house with beautiful pool area, lush gardens and great views, sleeps 41 / 17
    (19)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • DVD Player
    • Wi-Fi
    • Secure Parking
    • Central Heating
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 October 2017
    Beautiful Casa, stunning scenery, perfect quiet location but within easy reach of two amazing hilltop towns SAN Gimangino and Volterra. Our first time in Italy and fell in love...
    Reviewed 22 August 2017
    This holiday house and its setting far exceeded our already high expectations. The buildings are down a mile-long track, in the most stunning position imaginable. The gorgeous...
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    About this property
    Casa Florio' is a 2 bedroom apartment (upstairs apartment) incorporated into an ancient farm comprising 12 beautifully renovated stone buildings . Designed in traditional Tuscan country style with chestnut beamed ceilings and terraccota tiled floors. It is light and spacious with doors leading...
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    FIRENZE, San Gimignano, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Restored stone built villa near San Gimignano1 / 19
    (18)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Balcony
    • Washer
    • Patio
    • Central Heating
    • Grill
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 June 2018
    Just spent four days in this lovely old farmhouse, it is one of only a few privately owned villas, totally peaceful and relaxing, we only saw one other person there so had the...
    Reviewed 14 May 2018
    A comfortable home in a beautiful part of the world.Tuscany is really special. The images of hills covered in wheat, vineyards, olive groves, cypress trees and spring flowers...
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    About this property
    Podera collinella is ideally situated in a beautiful rural location with fabulous panoramic 360 degree views. The villa is a newly renovated 16th century converted farmhouse with a light & open feel. It has all 21st century amenities with well equipped bathrooms & kitchen and bespoke locally made...
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    50500, San Gimignano, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Independent villa with private pool in Tuscany - 3 bedrooms1 / 46
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
    • Wi-Fi
    • Washer
    • Balcony
    • Grill
    • Private Outdoor Pool (Unheated)
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 August 2017
    A superb, newly renovated farm house belonging to the owner's family since the 17th century. Whilst preserving its charming character , the house is an extremely comfortable...
    Reviewed 30 June 2017
    This is a gorgeous farmhouse converted lovingly to a residence. Grazia has decorated it in the beautiful simplicity of the Tuscan style. It is located about 30 min from Siena...
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    About this property
    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,...
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    53048, Siena, Province of Siena
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    I'l Granario - Lovingly restored stone-built Tuscan barn1 / 25
    (50)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Patio
    • DVD Player
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 October 2017
    Firstly I must say how helpful Steve the owner was. From questions before the booking to questions about the Sky box when we were there.Can't fault the house and the amenities...
    Reviewed 8 August 2017
    Couldn't fault anything with regards to the booking process,communication with the owner Steve and the property. Very detailed driving directions and information regarding the...
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    About this property
    Podere Torricchi is a small collection of beautifully renovated 16th Century farm buildings converted into houses and apartments. Set on a hill the entire site has stunning views of the rolling Tuscan countryside. I'l Granario' is a house set on two floors, tastefully renovated to retain...
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    FI 50050, San Gimignano, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Torre Farmholiday  Tuscan Chianti with pond1 / 79
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 3 Quick View
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    • Washer
    • Porch
    • Patio
    • Grill
    • Wi-Fi
    • Central Heating
    • Secure Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 February 2018
    We loved our stay on Podere Tegline, a wonderful farm from Roman times in the middle of the Chianti area and taken good care of by the family for many centuries. Our apartment...
    Reviewed 6 February 2018
    Wow! This was an incredible place to stay - full of history and so much love! The house and the surrounding land was absolutely gorgeous!! The hosts, Simonetta and Giovanni...
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    About this property
    Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce Chianti Classico wine and extra virgin olive oil organic.We restored the farmhouse of the 15th century and Giovanni has personally followed all the works to preserve the history of...
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 3
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    53017, Radda in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    La Casina Toscana, central with parking and wi-fi1 / 21
    (56)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Balcony
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Patio
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 May 2018
    We loved the villa and found it to be a picture perfect setting, very close to town, grocery and centrally located to many hill top towns in Tuscany and Umbria. The villa was...
    Reviewed 17 March 2018
    05th March to 14th March 2018 La Casina Toscana is everything you would wish for a stay in the beautiful countrysideof Montepulciano - The house is beautiful-,clean & cozy...
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    About this property
    Placed in the countryside of Montepulciano, near the most important historical towns such as Pienza, Montalcino and Bagno Vignoni, the Casina Toscana is a historical residence of the nineteenth century, which allows guests to enjoy the tranquility and relaxation that this place offers. The Casina...
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    53045, Montepulciano, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    very central large quiet flat 10+ Duomo1 / 26
    (4)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Central Heating
    • Balcony
    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 June 2018
    First like: the apartment is located on the ground floor. As a family of 4 with 5 bags, this made moving in & out a breeze. As advertised, the apartment is indeed spacious...
    Reviewed 4 November 2017
    This large spacious ground floor flat is perfectly located in the centre of Siena. Beds linen towels etc of the highest quality. A fully equipped kitchen is available but you...
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    About this property
    This is my holiday home in Siena, my home town. I have tried to tell you everything you need to know in my description, but please do not hesitate to ask me questions before booking - I am fluent in English, French and Italian. The flat is on the ground floor, on the same level as the street so...
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    Location Information
    53100, Siena, Province of Siena
    Condo/Apartment - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Casa Parva1 / 42
    (28)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • DVD Player
    • Wi-Fi
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 April 2017
    We loved our stay at Casa Parva - authentically medieval, recently restored and decorated to a very high standard, in a quiet and remarkably well-preserved hilltop village...
    Reviewed 14 November 2016
    Although we are frequent visitors to Italy, our Casa Parva stay was our first time in Southern Tuscany. It is hard to anticipate what to expect from a one street town with...
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    About this property
    A one-bedroom romantic apartment in a charming Medieval village in Tuscany. The village is off the beaten track and yet very close to the world known countryside of Tuscany and its most important art cities and wine districts. Pienza and Montepulciano are only 20 minutes away; Cortona, Siena,...
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    Location Information
    53020, Montisi, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Fonte Tuscany Holiday Apartment Chianti with pond1 / 72
    (7)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Outdoor Dining Area
    • Balcony
    • Secure Parking
    • Central Heating
    • Wi-Fi
    • Porch
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 February 2018
    We had a fantastic time during our stay in Tuscany. Simonetta and family were so friendly and helpful in suggesting places to see and things to do in the area. To top it all off...
    Reviewed 29 March 2017
    If you want to feel the real Tuscany, this is the perfect stay for you! My family and I stayed in this lovely house in September 2016 and enjoyed every second of it. The...
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    About this property
    This Apartment named Fonte, for two people, ( and 2 little children under 12 years old) is the most independent apartment of the farmhouse (64 square meters), with a large living room with direct access to private garden, a well equipped kitchen with fridge, stainless steel sink, microwave,...
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    Location Information
    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Amazing Tuscan holiday apartment in the historical Town centre of Colle di Val d'Elsa, sleeps 41 / 35
    (33)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Terrace
    • Central Heating
    • Washer
    • Private Garden
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 June 2017
    In the old part of Colle this apartment could not be more convenient.Fabulous internal facilities, we were very at home.Would have been too tight for 4 adults, but a...
    Reviewed 9 October 2016
    We stayed at Dietra Le Mura for a week. The two bedrooms apartment, each with its own bathroom, was perfect for our needs. Antonella and her husband were wonderful hosts, and...
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    About this property
    The Dietro Le Mura holiday home has been completely renovated and is located in the historical town centre of Colle di Val d'Elsa, a characteristically medieval town steeped in history. The apartment is on the first floor, has its own entrance and possible parking at just a few dozen metres away....
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    Location Information
    53034, Colle di Val d'Elsa, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Fonte Aulente Montalcino1 / 26
    (31)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    • Central Heating
    • Outdoor Dining Area
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2017
    This is a really gorgeous place to stay. The views could not be better, the garden is eclectic and the pool is warm and inviting. We were slightly unsure whether to book based...
    Reviewed 10 November 2016
    Our family thoroughly enjoyed this stay in Tuscany. My husband and I have been to Italy many times, but this is the first time we brought the kids with us. (Ages 3 and 6...
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    About this property
    Fonte Aulente is a Tuscan farmhouse from the 12th century recently restored and surrounded by beautiful garden-park, 2 km from the center of Montalcino, in a panoramic position with amazing views over the Tuscan hills. The apartment is a part of the old farmhouse, with its own entrance. The...
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    Location Information
    53024, Montalcino, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    LA VALIANA Luxury Villa Rental (Montepulciano) - HEATED POOL Incl./ FREE WI-FI1 / 88
    (33)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Mountain Views
    • Housekeeping Included
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 May 2018
    We arrived at La Valiana between visits to two beautiful Italian cities, Florence and Venice. It was our time in Tuscany and the plan was to visit area hill towns while staying...
    Reviewed 6 May 2018
    It starts before you actually get to La Valiana, when you communicate with the owner Cecilia with any questions about the area or the visit. The responses come quickly and are...
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    About this property
    LA VALIANA is glad to welcome you in the very heart of Tuscany, right midway among Montepulciano, Cortona and Trasimeno Lake. This elegant villa has been thought as ideal accommodation for independent travellers (max. Occupancy 8) desiring to experience the more authentic Tuscan lifestyle, for a...
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    Location Information
    53045, Montepulciano, Province of Siena
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Casa Verbena, 3 bedrooms apartment, first floor, terrace1 / 43
    (28)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Garden
    • Terrace
    • Central Heating
    • Washer
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    As long as you are happy to drive, the lovely towns of San Gimignano, Siena and Volterra are within easy reach, all worth visiting. I booked this very simply through TripAdvisor...
    Reviewed 1 August 2017
    We were staying for 2 weeks (2 adults, 1 kid 7 yeas) at this place. It was an absolute pleasure.Great and clean apartments, great pool and lovely and very friendly hosts.A...
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    About this property
    The apartment is placed in the hamlet of Castel San Gimignano, very near to the best famous cities as Siena, Firenze, San Gimignano, Volterra and the sea is reachable in less than an hour by car. You can also start from here for a relaxing walk or ride through the olive groves and the surrounding...
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    Location Information
    53030, Castel San Gimignano, San Gimignano
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Torre Moreschini1 / 19
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Washer
    • Wi-Fi
    • Private Garden
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 June 2018
    If you are looking to avoid tourists and feel the pace of a small medieval town, this is it! Anna and Andrea are super sweet hosts, willing to help with requests. They are very...
    Reviewed 25 June 2015
    My wife, 7 month old daughter and I stayed here for 3 nights. Andrea and Anna were wonderful hosts, making sure we had everything we needed even to the point of having a high...
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    About this property
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    Location Information
    53049, Torrita di Siena, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Raperonzolo1 / 20
    (9)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Grill
    • Housekeeping Included
    • Patio
    • Mountain Views
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53040, Cetona, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Lovely detached cottage with view of San Gimignano1 / 26
    (24)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Central Heating
    • Washer
    • Secure Parking
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Great place, spacious, clean, and comfortable, with idyllic atmosphere and surroundings. And, above all, the great hospitality of the owner family!!!
    Reviewed 1 October 2017
    a real home from home nothing missing. good location good base to visit all of tuscany very family frendly.
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    About this property
    Surrounded by idyllic countryside, this pretty holiday home contains flat-screen TV, free Wi-Fi and a barbeque. Parking is available onsite as is gas central heating. Decorated in a typical country-style using rustic furniture and bright terracotta floors, the airy home contains 2...
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    Location Information
    53037, San Gimignano, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Holiday Apartments near Pienza1 / 22
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Grill
    • Wi-Fi
    • Central Heating
    • Shared Garden
    • Balcony
    • Parking
    • Terrace
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 September 2016
    Travelling with a young family we found everyone incredibly welcoming. Loved the views and the pool. Great sized apartment and a 20 min walk into town despite feeling peaceful...
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    About this property
    This lovely country house with pool in Tuscany is located at 1.5km from the beautiful medieval village of Torrita di Siena, in the heart of Val di Chiana, only 15 km from Pienza and Montepulciano, and 48 km from Siena. Situated on a knoll, the 18th-century farmhouse is surrounded by its vineyards...
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    Location Information
    53049, Torrita di Siena, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Bright, spacious villa with pool near Siena1 / 39
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 June 2017
    Could not have been more perfect!Spacious, comfortable and location was ideal, as close to all main attractions, although still had a country feel.Pool area was wonderful...
    Reviewed 1 April 2016
    We have been there in October 2015 and it was a lovely journey. The house has 3 bedrooms and 2 bathrooms. The surrounding is really beautiful and it's about 5 min from the...
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    About this property
    Key points: large apartment (140 m2) in a farmhouse renovated with taste and attention to details. Terrace and independent entrance into the courtyard of the property, large pool with view and garden-park with olive grove. Fully equipped kitchen, comfortable living room, bedrooms with exposed...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Pornano1 / 16
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Shared Garden
    • Wi-Fi
    • Central Heating
    • Grill
    • Washer
    • Secure Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 May 2018
    I went to Pornano as a refuge from the urban streets of London and to practise my basic knowledge of the language. The apartment provided privacy and a great sense of peace...
    Reviewed 19 December 2014
    Pornano is a very comfortable place to base a visit to Chianti. We loved our stay there. The apartment itself had everything, and the Grumbles, the couple who own it, were so...
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    About this property
    The accommodation comprises of one double bedded bedroom with en suite bathroom and very well equipped living room/kitchen area looking out onto a pleasant flowery courtyard. Ideal for a couple seeking peace and solitude and it is centrally located to visit Florence, Siena and the many small...
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    Location Information
    53017, Radda in Chianti, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    LUXURY APARTMENT WITH PRIVATE GARDEN & VIEWS1 / 24
    (39)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Washer
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    • DVD Player
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 April 2018
    This apartment is perfect, there is everything there that you could possibly need for a perfect holiday.The apartment itself is lovely but you also have the advantage of a...
    Reviewed 5 October 2017
    Loved, loved this classy apartment. John and Tracy (the owners) keep it stocked with everything you could possibly need to really enjoy being at home away from home, including...
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    About this property
    Ideal for couples looking for a relaxing romantic holiday, we provide everything you need in our fully equipped and tastefully decorated apartment, see our reviews. FREE WI-FI Walking distance to local restaurants. The large private garden for your exclusive use overlooks the village of Gaiole in...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Tuscan Tower - A unique castle apartment1 / 17
    (19)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Central Heating
    • Grill
    • Internet Access
    • Terrace
    • Patio
    • Outdoor Dining Area
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 October 2017
    Great place in a great location. Very helpful owner (John) who ensures that each guest has a great experience while in being in Tuscany. This town (Montefollonico) is ideally...
    Reviewed 13 January 2017
    Wonderful location and wonderful apartment. John, the owner, was extremely attentive and helpful. We wished we had longer here.
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    About this property
    Torre Montefollonico is a magnificent two bedroom apartment in the tiny hilltop village of Montefollonico, a 10 minute drive from Montepulciano. The spacious apartment with two bedrooms, a library, a 12th century tower with rooftop patio, and two full private baths, can sleep four. The...
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    Location Information
    53040, Montepulciano, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Villa di Geggiano1 / 56
    (9)Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Balcony
    • Air Conditioning
    • Housekeeping Included
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 May 2018
    Great host and guided us through his historical family home. View was breathtaking. Modernized Villa.
    Reviewed 15 May 2017
    We were very lucky to spend 4 nights at Villa di Geggiano with friends. It truly is a special place. If your dream is to be situated in the rolling vineyards and olive groves of...
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    About this property
    One of the original, charming and elegant garden pavilions, situated within the garden of Villa di Geggiano, has recently been renovated into two luxury suites which have now been opened to guests for reservation. The Pavilion has a total capacity of 4 persons but it has been designed to be...
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    Location Information
    53019, Siena, Province of Siena
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 4
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    Holiday Apartment in historical palace.Marina1 / 46
    (12)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Central Heating
    • Washer
    • Mountain Views
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    We stayed at the Holiday Apartment for one month and found that the location of the apartment within Montepulciano and within all of Tuscany to be the perfect location for our...
    Reviewed 23 November 2017
    We stayed in this beautiful apartment for 4 nights.Absolutely fantastic!!Both bedrooms are en-suite with showers.Beds are comfortable but very nice pillows.Kitchen with all...
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    Location Information
    53045, Montepulciano, Province of Siena
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Luxurious Vacation Rental at Palazzo Cinotti in Si1 / 20
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 November 2017
    The apartment is exactly as pictured and described. No photoshop; no hyperbole. The location is perfect, on Siena's main street (dual-pane windows eliminate noise). Kitchen and...
    Reviewed 5 September 2017
    We spent a month in Siena and stayed in two different suites offered by Antonio and Alexandra, the gracious and unobtrusive hosts. The apartments have high ceilings and are...
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    About this property
    The Palazzo Cinotti, historical residence, is located in Siena Tuscany along the exclusive via di Citta', between the square il Campo and the cathedral. The apartment is 135 sq ft, with three bedrooms and two bathrooms, suitable for families with children, young couples, and sophisticated...
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    Location Information
    53100, Siena, Province of Siena
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Casa Lorenzo: Charming Tuscan house,pool, AC,WiFi1 / 40
    (12)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2017
    A comfortable and well-equipped house in a beautiful setting. The village has several food shops and two restaurants and there are numerous places to visit in the area.
    Reviewed 23 October 2016
    From the time I first corresponded with Federica, I knew this place was special. She was so very helpful. Because we were not arriving until late, she arranged for a cook...
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    About this property
    Casa Lorenzo is a small indipendent antique house suitable for 5 +1. 'what a beautiful charming house you have;we expecially enjoyed the view from the pool ;unparalleded beauty! San Giovanni is a wonderful little town..although we enjoyed all of our day excursion to Montalcino,Montepulciano etc. we...
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    Location Information
    53020, San Giovanni d'Asso, Montalcino
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 5
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    Podere Val delle Corti1 / 24
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Grill
    • Private Garden
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 2015
    My wife and I have vacationed in the Radda area several times over the past decade or so. All of the rentals we had were nice but "The Barn" is far and away our...
    Reviewed 22 October 2014
    Just returned from a delightful one week stay with Lis and Roberto at Val delle Corti. "The Barn" (guest house) is large, well appointed (including a full kitchen), and...
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    Location Information
    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Agriturismo Sammonti1 / 34
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
    • Parking
    • Terrace
    • Grill
    • Private Outdoor Pool (Unheated)
    • Central Heating
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 May 2017
    Our warm and wonderful host was available for anything we needed, yet gave us total privacy. The place was adorable, spacious and comfortable inside. Our towels had been dried...
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    About this property
    The “borgo Sammonti” was built in the beginning of the 13th century as a fortress in the county of Scorgiano, and it is located near most beautiful and important tuscan cities. The structure is surrounded by woods and it offers many paths for walks and escursions. The beauty of the view guarantees...
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    Location Information
    53035, Monteriggioni, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    antico casale delle more1 / 27
    (6)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Parking
    • Cable/satellite TV
    • Washer
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Internet Access
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    53048, Bettolle, Sinalunga
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms  Apartments (Camelia)1 / 19
    (6)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2017
    This comfortable, three level apartment, is very clean and located a short walk from the bus station and near a taxi stand. The air conditioning, wifi and water flow in the...
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    About this property
    Our Guesthouse is a renowned former residence of an aristocratic Senese family. a short walk from t the Piazza del Campo and next to the main bus.station (Piazza Gramsci) Our Apartments aim to offer a valid alternative to anyone who wants to live their Senese experience with total independence. We...
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    Location Information
    53100, Siena, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    VILLINO1 / 18
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Central Heating
    • Balcony
    • Parking
    • Terrace
    • Grill
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 November 2017
    The house itself is a unique proposition - on the edge of a really beautiful little town which is untouristy and has a real vibrant community, but once you are home you feel...
    Reviewed 14 July 2016
    Had a wonderful 5 night stay here - ideal for 2 couples with 2 bedrooms and 2 bathrooms. A lovely rustic farmhouse only a 10 minute walk from the charming little village of...
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    About this property
    Our Villino comfortably fits 6 people. It is unique because of its location: 10 minutes walking from the picturesque village of Montisi, immersed in the Tuscan hills and in an amazing peace and quiet. Surrounded by fruit trees and olive trees, with lots of land for your walks or to delight your...
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    Location Information
    53020, Montisi, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Agriturismo IL PODERUCCIO appartamento1 / 43
    (13)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Terrace
    • Mountain Views
    • Balcony
    • Grill
    • Washer
    • Parking
    • Housekeeping Included
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 October 2017
    A cosy house in a beautiful landscape. A clean flat with a well organised kitchen, comfortable sleeping rooms an enough space for a family with kids. And a very helpful and...
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    About this property
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    Location Information
    53023, Castiglione D'Orcia, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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