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Holiday Homes in Province of Siena

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    All 4 345 Rentals in Province of Siena
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    Elegant 2 bedroom apt. in historic Siena residence1 / 18
    (31)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Casa Parva1 / 42
    (28)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 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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    Chianti Cashmere Vacation Rentals, Rural Tuscany1 / 40
    (14)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Central Heating
    • Mountain Views
    • Grill
    • Patio
    • Washer
    • Balcony
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 July 2017
    I stayed in the cute, cozy apt that ajoins the main house. Not the big house rental with the pool. It's lovely. The bedroom is a loft space. For those of us who are vertically...
    Reviewed 2 October 2016
    Stayed a week in September 2016. It was fantastic, everything abou it was as described in the description., we were able to bottle feed Jellybean, pet the very friendly guard...
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    About this property
    Only 3 km from Radda in Chianti, and midway between Florence and Siena, our 25-acre farm is nestled into the side of a hill at the end of its own 300 meter gated gravel road, and consists of the original 300 year old remodelled stone farmhouse available for year-round rental, a nearby stone hay...
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    VILLA Le Corolline1 / 30
    (15)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Outdoor Dining Area
    • Grill
    • Balcony
    • Air Conditioning
    • Terrace
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    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 6 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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    Agriturismo Podere San Giusto1 / 10
    (11)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Central Heating
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Balcony
    • Grill
    • Parking
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2017
    Our four day stay was far too short! Fabio and Ursula were delightful and welcoming.They made our stay in this lovely area of Tuscany that much more special by giving us much...
    Reviewed 3 November 2016
    We thoroughly enjoyed our stay at Podere San Guisto! Fabio & Ursula were warm and welcoming, and very helpful in guiding us through the area and offering suggestions for...
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    53018, Sovicille, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Attico con altana: incanto e relax tra le bellezze di Siena1 / 22
    (1)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 24 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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    Villa PoliFlora1 / 43
    (25)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Wi-Fi
    • Washer
    • Shared Garden
    • Outdoor Dining Area
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 days ago
    Poliflora is a comfortable apartment, very cozy and with everything you need. It is located in a good place to visit the entire Orcia Valley. And the best, the hosts. Poli and...
    Reviewed 17 September 2017
    This location is excellent for being in the heart of Tuscany. The accommodations were very nice everything was well kept and clean. We enjoyed using this as our home base...
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    About this property
    Villa PoliFlora is a modern residence in Monticchiello in Val d'Orcia, a Unesco world heritage site. The owners and creators invite you for a relaxing stay, in the triangle among Montalcino, Pienza and Montepulciano. A few kilometers away from Siena and Chianti Classico, best destinations in...
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    53026, Monticchiello, Pienza
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Amenities & Details
    • 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 7 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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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Washer
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    DEAR TRAVELER, PLEASE KINDLY NOTE: The rental price includes: final cleaning; electricity; linens; towels. Available for a fee, if desired:heating (when needed);baby bed EUR 25.00/week. Refundable security deposit paid cash upon arrival: EUR 150. Casa Giobatta A is an elegant and welcoming...
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    53014, Lucignano d'Arbia, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Delightful 2 bedroom farmhouse with beautiful private grounds and pool1 / 24
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Balcony
    • Children's Pool
    • Cable/satellite TV
    • Air Conditioning
    • Terrace
    • Washer
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2017
    Just spent a week at Sarteano with my wife and two kids aged 10 and 12. This was our first villa holiday and it was great. The welcome by Bruna and Susana was lovely.I am an...
    Reviewed 26 April 2016
    Our stay was very relaxing and the villa and surrounding countryside was beautiful. Our hosts were very welcoming and accommodating. I would highly recommend this vacation rental.
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    About this property
    The Agriturismo Sferracavalli is the best way to enjoy Italian genuine food, which can be gathered in the back garden, and to feel compleatly plunged in peace and relax among Tuscany nature. Medieval villages complete the perfect Tuscany atmosphere all around, so that who wants to learn about...
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    53047, Sarteano, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Spacious Stone Villa in the Heart of Tuscany1 / 13
    (4)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 October 2017
    A clean, crisp, artistic and aromatic environment, powerful views of serene fields and woods, horses to rent and ride around amazing roads and trails. Coffee shops, markets and...
    Reviewed 22 October 2017
    I had a fantastic stay in Tuscany! The accommodations were spacious and luxuriant and had an authentic Tuscan flair. I was surrounded by beautiful artwork that I found out was...
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    About this property
    Magnificent stone villa in lovely hill town 20 minutes from Siena. Five spacious bedrooms furnished in country antiques. Wooded yard. Two fireplaces. Gas grill, large outdoor terrace. Outdoor dining area. Town has restaurant, three coffee bars, post office, general store and grocery store. Ample...
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    53016, Casciano, Province of Siena
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 9
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    3 bedroom farmhouse in the picturesque Tuscan hills boasting private pool, terrace and garden, sleeps 61 / 25
    (14)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Balcony
    • Grill
    • Cable/satellite TV
    • Washer
    • Central Heating
    • Children's Pool
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 November 2017
    Great location - in middle of village - one grocer, two restaurants and a church. So quiet and peaceful.What I liked - pool, veranda (come balcony), sculptures, location (walk...
    Reviewed 17 October 2017
    This villa in the small Tuscan hamlet of Iano, was perfectly located for our day trips to all the towns we wanted to see. Pisa, Lucca, San Gimignano,Siena, and others are all...
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    About this property
    Podere Le Monache set on a hillside dominates one of the most picturesque and spectacular landscapes in Tuscany. With distant views over hills, out to sea towards Livorno and Pisa. Originally a convent wrapped in history Le Monache has a magical and spiritual atmosphere. Whether you are lazing by...
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    50050, San Gimignano, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beautiful Tuscan countryside, Siena1 / 54
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Internet Access
    • Parking
    • Terrace
    • Balcony
    • Washer
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the splendid setting of the most celebrated and internationally known Crete Senesi and the typical Tuscany hills, apartment in semi-detached building on two levels suitable for a maximum of 6 people. Located in the quaint village of Mucigliani , an ancient castle replaced more recently by...
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    53041, Torre A Castello, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    53100, Siena, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    VILLA TALCIONA1 / 32
    (19)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Central Heating
    • Parking
    • Washer
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 October 2017
    This was our fourth stay and was as fantastic as the first! The views from the Villa are beautiful, the facilities excellent. Francesco and Elena are wonderful hosts, who can...
    Reviewed 5 October 2017
    Villa Talciona is surrounded by the beautiful Tuscan Hills. Surrounded by greenery and blue skies no better place to stay in Poggibonsi. The hosts, Francesco and Elena were...
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    53036, Poggibonsi, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 10
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    La Senesina , enchanting apartment near Siena1 / 27
    (7)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed 5 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 5 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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    Casa Vacanze San Giuseppe Villino Ginestra1 / 20
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
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    53025, Piancastagnaio, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    La Grancia Country Resort Apt11 / 49
    (7)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Parking
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Private Garden
    • Balcony
    • Shared Garden
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 June 2017
    What an amazing place to have as a home base for 5 days of exploring Tuscany. Claudia and her father were excellent hosts and provided very quick responses to any questions and...
    Reviewed 1 July 2015
    This is a country property with modern apartments built in a very old building - so things are not hotel perfect. The unit #1 apartment is very well equipped, although no...
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    About this property
    La Grancia Country Resort is a romantic and charming 14th century fortress used as a 'Grancia', a granary for the storage of the produce grown on the property. Perched next to the delightful hilltop village of Montisi, it overlooks the surrounding Tuscany countryside on a hill near Pienza,...
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    53020, Montisi, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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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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    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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    La Piccola Loggia1 / 17
    (13)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Parking
    • Wi-Fi
    • Patio
    • Balcony
    • Central Heating
    • Private Garden
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 July 2015
    If you are looking for the perfect getaway in the heart of Tuscany, then La Piccola Loggia in Torrita di Siena is the place to be. Surrounded by sunflower and corn fields, and...
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    53049, Torrita di Siena, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    Villa di Geggiano1 / 112
    (8)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 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...
    Reviewed 28 July 2016
    On a recent European trip with my husband and some close friends we had the pleasure of meeting Andrea and experiencing his working vineyard. The accommation is separate to the...
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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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    53019, Siena, Province of Siena
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 4
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    Cottage with pool for 2 couples - May is at 40% off, 14-21 July at 20% off!1 / 30
    (14)Very good
    2 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 September 2017
    As wonderful as expected - even better; in any way: Location, facilities, rooms...Perfect for trips on the countrysideVery kind ownersalso recommendable for families with...
    Reviewed 16 June 2017
    My family and i had a fantastic and absoultely relaxed holiday at PetrAlexa. You only hear the birds, when you wake up. You feel so free in the big garden and the Chianti Hills...
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    About this property
    Ciao from Petra &Alexa and thank you for stopping by! ***Spring Promotion*** Take advantage of our 20% off on May weeks! PLEASE BE AWARE!: We can only accept WEEKLY bookings with change-over day on SATURDAYS: so 7 nights or multiple of 7 (7-14-21… nights). Otherwise we need to CANCEL the booking....
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    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 6
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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 6 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 4 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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    53100, Siena, Province of Siena
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    La Torre di Carlo1 / 52
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 September 2017
    A wonderful two night in this four story turret style accommodation in the charming village of Monticchiello.
    Reviewed 4 July 2017
    As shown in the photograph, the tower is of mediaeval vintage. It was converted some 20 years ago to provide accommodation over four floors: one (fairly small) room per floor...
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    53026, Monticchiello, Pienza
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Holiday Apartments near Pienza1 / 22
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Grill
    • Wi-Fi
    • Central Heating
    • Shared Garden
    • Balcony
    • Parking
    • Terrace
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 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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    53049, Torrita di Siena, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Valdorcia1 / 15
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The property is dated back XVIII century, has been completly restored saving the antique charme. In the centre of the village, distance by walk 3 resturants, cofee bar, grocery, bakery bank and tourist office. If you wish relax , good food good wine art and history you will enjoy a perfect...
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    Location Information
    53026, Monticchiello, Pienza
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, 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 2 weeks ago
    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 2 weeks ago
    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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    Borgo Calcinari di antonella del Sordo oasidipace1 / 31
    (7)Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Patio
    • Wi-Fi
    • Outdoor Dining Area
    • Porch
    • Shared Garden
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2016
    We spent wonderful days in this appartment with our children. The area is very quiet and the river near by makes for great swimming. The appartment had all the neccessities and...
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    53018, Brenna, Province of Siena
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 6
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    Stunning Tuscan views from traditional farmhouse 10mins to downtown Siena1 / 31
    (8)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Balcony
    • Central Heating
    • Mountain Views
    • Porch
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 September 2017
    Short distance from downtown Siena and all the sites and history it has to offer. Charming farmhouse villa nestled on a hill overlooking incredible countryside. Each window...
    Reviewed 6 July 2017
    We stayed here for 4 days while visiting nearby sites. The rooms were well furnished with beautiful furniture, some of which looked like antiques. The beds were comfortable...
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    About this property
    This beautifully renovated rustic villa is only 10 minutes' drive from the heart of Siena. Built in the 1500's, Belvedere (beautiful view) is situated on a remote hilltop with breathtaking views of the Tuscan countryside with vineyards and olive trees in the immediate vicinity. It's near enough for...
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    Location Information
    53100, Costalpino, Siena
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Cozy house with best view in Cetona1 / 31
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Mountain Views
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 January 2017
    What a lovely place. The city of Cetona instantly stole our hearts. So small and cozy, with sepctacular views over the hills of Tuscany and their morning fogs, narrow streets...
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    About this property
    Hello, we are Maria and Kirill and are glad to welcome you in our house. The house is located in the historic city center of Cetona by the edge of the city wall, so that from the street in front of the house and from the bedrooms’ windows you will find stunning views over the fields and hills of...
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    53040, Cetona, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Tuscan Style House Casetta1 / 21
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Washer
    • Private Garden
    • Wi-Fi
    • Central Heating
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2017
    La Casetta was even better than we had imagined. Our host Patrizia, welcomed us with a freshly baked fruit pie, a bottle of her own superb wine, home-made jam, and various other...
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    53040, Cetona, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    CASALE ROSANNA1 / 21
    (6)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Central Heating
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 November 2017
    Beautiful place in a lovely setting , just the right distance from San Gimignano for a good hike, or to veiw it's iconic towers from afar . Sadly they had closed the pool , as...
    Reviewed 18 October 2016
    Perfect location for visiting all of Southeast Tuscany. Lovely and welcoming hosts (no English spoken but you're in Italy so talk with your hands!). Stunning panoramic views of...
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    53037, San Gimignano, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    New Casa Titta apt 3 bedrooms , amazing view1 / 14
    (8)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Parking
    • Private Garden
    • Wi-Fi
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 September 2017
    A beautiful apartment set in fabulous grounds, ideally situated to explore Tuscany. Our first visit to Italy and we could not have picked a better location, ideal for exploring...
    Reviewed 5 August 2017
    I've already reviewed the wonderful Casa Titta from our last two visits in 2015 and 2016, but just as we come to the last couple of days here again, I thought it worth...
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    About this property
    C asa Titta is our third apartment ,completely new ,really comfortable, placed on the first floor with three bedrooms for 5 people and a large open space living . A new kitchen equipped with dishwasher , fridge/freezer, microwave and electrical hoven. The bathroom has a large shower and a little...
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    Location Information
    53030, Castel San Gimignano, San Gimignano
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Casa Degli Olivi Cetona , Siena Tuscany1 / 17
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Secure Parking
    • Terrace
    • Balcony
    • Shared Garden
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 October 2017
    Cosy apartment a short walk from the historic town of Cetona and conveniently situated for exploring other parts of Tuscany and Umbria. Adrian, the owner, was very friendly...
    Reviewed 29 September 2017
    We have just spent a very enjoyable week at the Casa degli Olivi, it was spotlessly clean, with beautiful views and a friendly and very helpful host, A great place to stay and...
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    About this property
    The apartment is attached to the owner’s home and sits along side the strada del polaco (SP.321) on the outskirts of the historic town of Cetona. This organic smallholding overlooking vineyards, olive trees and sunflowers. It is in the country, but still convenient for touring the rest of Tuscany...
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    Location Information
    53040, Cetona, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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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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    • 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 2 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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    Location Information
    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Lovely and little panoramic 'Mansarda'1 / 20
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Terrace
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 April 2015
    Pilar and Grazziele are amazing hosts. Pilar speaks english so it makes everything easier.You can go easily to Siena, Montepulciano or Firenze by car in less than an hour...
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    About this property
    The apartment (60m2 - approx. 600 sqf) is located on the top floor and is made up of 4 beautifully-decorated rooms with a light blue pastel colour motif. The holiday flat has one double bedroom, with ample storage space and in the living room there is a double sofabed. Mansarda has one bathroom...
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    Location Information
    53015, Monticiano, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Apartment Camilla, countryside, not far from Siena1 / 17
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Grill
    • Parking
    • Outdoor Dining Area
    • Central Heating
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 October 2017
    What a wonderful place to stay. So very spacious for the four of us, great kitchen, bedrooms and baths. And, much to my personal pleasure, washers and dryers. So very quiet...
    Reviewed 20 September 2016
    We have just returned from our fantastic stay at Apartment Camilla, Podere Incrociati. Myself and partner along with my parents, absolutely loved this place. Great...
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    About this property
    Podere Incrociati rises in the heart of Montagnola Senese, just 15 km/9 miles far from Siena and 75 km/47,5 miles far from Florence, among the greenery of age-old oaks, holm-oaks and chestnut-trees. Thanks to its high position (500 mt./1640 ft. above sea level) you will enjoy a well-aired summer...
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    Location Information
    53018, Siena, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Central Heating
    • Shared Garden
    • Parking
    • Terrace
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful holiday home is located at 200 mt from the pretty medieval village of Torrita di Siena, only 15 km from Pienza and Montepulciano, in the heart of Val di Chiana, an attractive valley in the south-east of the region. The farmhouse faces on a side the village and on the other side a...
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    Location Information
    53049, Torrita di Siena, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Casanova dei Boschi1 / 29
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 October 2017
    Last stop to relax with friends for a couple nights, after 2 weeks of touring Rome & Florence, before heading home. It was perfect. Beautiful views from every window. Very...
    Reviewed 9 December 2015
    I cannot express how deeply satisfied we were with the villa and support received from Mr Franco. Our expectations were exceed at every turn; from the grounds to the expansive...
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    Location Information
    53011, Montepulciano, Province of Siena
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    I MELOGRANI II: 3BDR Tuscan villa,view,pool,WiFi1 / 41
    (2)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Grill
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Private Garden
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2017
    The small village location was a perfect for our visit to the Tuscany area. We were able to use this central location to visit many beautiful villages like Montepulciano, Siena...
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    About this property
    I MELOGRANI II is a section of a villa settled in the heart of Siena countryside :I MELOGRANI I. WHEN THIS PART OF THE HOUSE IS RENTED THE OTHER PART REMAINS CLOSED AND VACANT. This beautiful house is surrounded by a fenced olive grove with private pool (12x5), lawn, stunning view on rolling...
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    Location Information
    53020, San Giovanni d'Asso, Montalcino
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Castello di Montalto - 3 Bedroom Villa in Chianti1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Outdoor Dining Area
    • Central Heating
    • Grill
    • Internet Access
    • Washer
    • Mountain Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 October 2013
    Firstly, I Have traveled all over the world and have only stayed at Chateau Relais or 5 star hotels.Staying at Montalto has been the most wonderful,romantic,amazing experience...
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    About this property
    Montalto is a true medieval castle located in the beautiful Chianti region of Tuscany, near Siena. The owners live here all year round and offer the houses of the little hamlet as vacation villa rentals. There are two 3-bedroom villas for rent, each suitable for 6 people:'Casa del Guardia' and...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Holiday lodging near Pienza P51 / 28
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Central Heating
    • Wi-Fi
    • Parking
    • Balcony
    • Grill
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 December 2016
    We travelled to this accomodation after several days in Pisa and Florence, and as soon as we arrived, we realised we had made a great choice.The house is very pretty and...
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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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Pure 5 star Luxury in Tuscany-Jacuzzi-AC-wifi-S1 / 23
    (7)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Mountain Views
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 August 2017
    Fantastic base for a group of photographers. It was great to chill out on the terrace after early starts . Everyone had there own space and we never felt crowded
    Reviewed 25 March 2017
    This was a wonderful apartment. Very well appointed and comfortable. Beautiful terrace with stunning views of Southern Tuscany. Well equipped kitchen. Very walkable to town...
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    About this property
    New lower price - one of the nicest flat in Tuscany 5 star standard !! The apartment has its own entrance and occupies the whole 1st and top floors of this classical building next to the ancient city wall. Private parking, large roof terrace (55m2) with great views over the valley and...
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    Location Information
    53027, Pienza, Province of Siena
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Holiday Apartment in historical palace.Marina1 / 46
    (11)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 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...
    Reviewed 15 May 2017
    Spent two nights at the Historical Palace while on a family trip to Tuscany. The location was great, the sceneries from the apartment awesome and the flat comfortably...
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    53045, Montepulciano, Province of Siena
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Torrita di Siena flats A1 / 13
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Shared Garden
    • Terrace
    • Parking
    • Central Heating
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful holiday home is located at 200 mt from the pretty medieval village of Torrita di Siena, only 15 km from Pienza and Montepulciano, in the heart of Val di Chiana, an attractive valley in the south-east of the region. The farmhouse faces on a side the village and on the other side a...
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    Location Information
    53049, Torrita di Siena, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Housekeeping Included
    • Washer
    • Air Conditioning
    • Wi-Fi
    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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    Location Information
    53100, Siena, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Fattoria il Musarone - La Tramontana. Sinalunga1 / 18
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Parking
    • Grill
    • Central Heating
    • Washer
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2016
    A lovely location, set in open countryside and offering all you would want from self catering accommodation - plus a very inviting pool to cool off in at the end of a hot...
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    About this property
    In the heart of the countryside only 40 minutes from Siena five beautiful apartments have been made by restoring an old Tuscan country house set on a hillside with views all around. Each apartment retains its fascinating original characteristics. A courtyard around the house is shaded by pines and...
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    Location Information
    53048, Sinalunga, Province of Siena
    Condo/Apartment - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Casa Verbena, 3 bedrooms apartment, first floor, terrace1 / 43
    (26)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Shared Garden
    • Terrace
    • Central Heating
    • Washer
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 28 June 2017
    We couldn't have asked for a better vacation location. The breath-taking views were only matched by the hospitality of the owners and their parents. Our apartment was furnished...
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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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