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Cheap Province of Siena Holiday Homes

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    Travellers to Province of Siena are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    1,120 Matching Rentals in Province of SienaView all 4,476 rentals
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    San Gimignano: Tuscan farmhouse apartment1 / 7
    (1)Average
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Santa Caterina b&b1 / 10
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Santa Caterina Bed and Breakfast1 / 8
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    A BEAUTIFULLY RESTORED FARM HOUSE IN MONTERIGGIONI, LOCATED 5 KILOMETERS FROM SIENA AND 56 FROM FLORENCE. Bed and Breakfast Santa Caterina is the ideal starting point for day-trips in the Chianti countryside. Our reasonable prices, the clean and cosy rooms, the friendly environment and our...
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    53035, Monteriggioni, Province of Siena
    Private Room - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Central Heating
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    53048, Farnetella, Sinalunga
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    53100, Siena, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Affittacamere Caliani1 / 15
    (1)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    53024, Buonconvento, Province of Siena
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
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    53023, Vivo d'Orcia, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Appartamento campagna Toscana1 / 24
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    53036, Poggibonsi, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
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    53040, Cetona, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    APPARTAMENTO A TORRITA DI SIENA1 / 19
    (4)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    53049, Torrita di Siena, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    53019, Castelnuovo Berardenga, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Casa Gioconda Crete Senesi1 / 26
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Secure Parking
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    Reviewed 20 March 2017
    We loved the views of the surrounding countryside. We will never forget sitting watching the sun set while the abbey bells tolled.
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    About this property
    Enjoy a relaxing trip in the area of Sienese Clays, a breathtaking corner in Tuscany! My flat is located Chiusure, a small village equidistant from Siena, Pienza and Montalcino and a short walk from the Abbey of Monte Oliveto. The village has two restaurants and a small drugstore: pharmacy, bank...
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    53041, Siena, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    About this property
    Characteristic and small group of farmhouses made up of 3 units set inside a large property which covers an area of about 460 hectares near Castellina in Chianti. Peaceful and panoramic position amidst the vineyards and gently rolling hills of Chianti Classico (350 m a.s.l.). The 3 structures has...
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    53011, Castellina In Chianti, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    One Bedroom Ground Floor Apartment San Gimignano1 / 9
    (10)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    Pet friendly
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    Reviewed 18 September 2015
    We stayed here for 6 nights - it was a great little apartment in a nice complex. Pretty busy as you would expect in August. The owners are very friendly - they don't speak much...
    Reviewed 15 September 2012
    We couldn't find many reviews on this property before booking but decided to go ahead anyway. We were so happy with our weeks stay here. Le Volte is a great apartment - good...
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    About this property
    Enjoying beautiful views of the rolling green hills and the towers of the city, The characteristic Le Volte apartment at Il Casolare lies in splendid countryside just over 3km from the medieval town of San Gimignano. Composed of two traditional Tuscan farmhouses and a cottage, Il Casolare is...
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    53037, San Gimignano, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    Typical stone-built farmhouse that has been completely renovated and is situated inside a large, active farm that is completely fenced-in and immersed in the gentle landscape of the Tuscan hills. Located in the heart of the Elsa Valley in a particularly strategic geographic position for visiting...
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    53034, Colle di Val d'Elsa, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Typical stone-built farmhouse that has been completely renovated and is situated inside a large, active farm that is completely fenced-in and immersed in the gentle landscape of the Tuscan hills. Located in the heart of the Elsa Valley in a particularly strategic geographic position for visiting...
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    53034, Colle di Val d'Elsa, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Tuscan Villa Argiano 1 room,Montepulciano, B&B1 / 23
    (1)Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    in Villa Argiano in Montepulciano, we have several possibilities : B&B in Argiano's villa rooms ( three ) or self catering apartments ( two + one extra room ). In this beautiful Villa, were we live , at the second floor of the house we rent three bedrooms in b&b service . Breakfast is served...
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    53045, Montepulciano, Province of Siena
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 2
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    Tuscany Villa in  Argiano near Montepulciano B&B  1 Room,  swimming pool, wifi1 / 18
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    In the beautiful ancient Villa ( 1812 ) of the of ' Tenuta Argiano in Montepulciano ' estate , we rent some bedrooms in B&B treatment . our guest are treated like part of the family and if request they can join the dinner with the owners. this place is ideal also for guest who want to improve...
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    53045, Montepulciano, Province of Siena
    Private Room - 2 Bedrooms, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    About this property
    Tenuta di Argiano a Montepulciano, located near MONTEPULCIANO, is surrounded by vineyards growing grapes for the famous local wines, Vino Nobile di Montepulciano and Rosso di Montepulciano, and is peaceful and quite. swimming pool and wifi . bikes tour, spa nearby, Italian course at Montepulciano...
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    53045, Acquaviva di Montepulciano, Montepulciano
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    53100, Siena, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    53100, Siena, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 1
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    3 Bedrooms, 1 Bathroom, Sleeps 1 Quick View
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    53037, San Gimignano, Province of Siena
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 1
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    53041, Asciano, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Relax alla casa di Pasquino1 / 37
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Private Garden
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    53015, Monticiano, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
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    About this property
    Rocche di Valiano is an ancient village situated in the heart of Chianti area near Siena. The structure, completely surrounded by olives groves, enjoys a spectacular view of the typical Tuscany landscape made by sweet hills and of the vast vineyards. The recent renovation doesn’t have altered...
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    53019, Quercegrossa, Monteriggioni
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Holiday Apartments near Pienza1 / 22
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Grill
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    Pet friendly
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    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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    53049, Torrita di Siena, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    A casa di Vasco (2) - restored farmhouse, located in Tuscany Chianti1 / 33
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Terrace
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    Pet friendly
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    Reviewed 24 April 2018
    The flat was very clean, comfortable and with a fantastic view. It was recently renovated to high standards while retaining the charm and typical features of a Tuscan house. The...
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    53019, Castelnuovo Berardenga, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    Hilltop Retreat for Couples, a Rural Romance1 / 60
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Balcony
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    Pet friendly
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    Reviewed 11 November 2016
    Good for families with kids that need a home base in Tuscany. Pretty spacious, and a good location in the area. Recommendations and tips by the owners in there info binder...
    Reviewed 22 October 2015
    The accommodation is very nice. Everything you need is available and the owners gave us very good tips about restaurants, cheap or even free parking spots and places to visit...
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    About this property
    This property is the ideal all-season retreat for couples, including those with a baby or toddler, not bound by school holidays, looking for quieter seasons and cooler weather. We welcome young couples, mature and retired couples. There is a sun bed that doubles as a camp-bed/cot for an older child...
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    53037, San Gimignano, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Terrace
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    About this property
    Merlino is located in a pretty barn on a small family run farm just 7km from San Gimignano with its historic monuments, many craft shops, various restaurants and open air swimming pool. There are pleasant views of the Elsa Valley from the farm which produces wine and olive oil and they have an...
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    53036, Poggibonsi, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    53040, San Casciano dei Bagni, Province of Siena
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    • Mountain Views
    • Children's Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
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    53040, Celle sul Rigo, San Casciano dei Bagni
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    53019, Castelnuovo Berardenga, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    53019, Castelnuovo Berardenga, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    1 53035, Monteriggioni, Province of Siena
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    • Central Heating
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    About this property
    It is a cosy studio apartment which is part of the “Scuderia” building , with a direct entrance from the garden. It consists of a bedroom/living room with a double bed, a kitchenette and a bathroom with a with a shower,basin, toilet and bidet . There is garden furniture under the porch for your...
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    53100, Costalpino, Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    CHIANCIANO TERME - Appartamento ampio centro citta1 / 10
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    Reviewed 16 June 2017
    Most amazing find. Will return. Home from home. Brilliant hosts and made us feel like family from the minute we arrivèd
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    53042, Chianciano Terme, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    Monolocale nel Chianti per gustare olio/vino nuovo1 / 15
    (9)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    53034, Colle di Val d'Elsa, Province of Siena
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    53034, Colle di Val d'Elsa, Province of Siena
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    BED AND BREAKFAST THE HESITANT PILGRIM1 / 10
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    53034, Colle di Val d'Elsa, Province of Siena
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 12 Bathrooms, Sleeps 6 Quick View
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    53040, Gracciano, Montepulciano
    Holiday Rental House - 4 Bedrooms, 12 Bathrooms, Sleeps 6
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    agriturismo campovecchio - Appartamento Cipresso1 / 22
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    53019, Castelnuovo Berardenga, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    53100, Siena, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    53100, Siena, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Enjoying beautiful views of the rolling green hills and the towers of the city, the characteristic Nilo apartment at Il Casolare lies in splendid countryside just over 3km from the medieval town of San Gimignano. Composed of two traditional Tuscan farmhouses and a cottage, Il Casolare is divided...
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    53037, San Gimignano, Province of Siena
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Casa Laura is an independent apartment in a restored farmhouse Agriturismo la Magione that is situated on an agricultural estate on a hilltop at about 300 meters above sea level. It offers a wonderful panorama of the surrounding countryside with fields, olive groves, vineyards and woodlands. The...
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    53035, Monteriggioni, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    appa. in Casole D'Elsa via della corsina 681 / 16
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    XX, Casole d'Elsa, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    53042, Chianciano Terme, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Appartamento 3 posti a Chianciano Terme1 / 5
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Appartamento 3 posti nel cuore del borgo di Chianciano Terme, composto da 1 camera matrimoniale, soggiorno con divano letto singolo, bagno con doccia, cucina. L'appartamento si trova in un palazzo in posizione sopraelevata con affaccio sulla valle sottostante. Si trova a pochi minuti dalle note...
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    53042, Chianciano Terme, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    B&B Antico Granaione Poppy bedroom1 / 26
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    Antico Granaione b&b, stylish hotel in Tuscany, is located in the characteristic hamlet of Serre di Rapolano close to the thermal baths of Rapolano Terme, Siena. Antico Granaione b&b proposes relaxing holidays surrounded by the amazing landscapes of Crete Senesi, the Southern province of Siena....
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    53040, Serre di Rapolano, Rapolano Terme
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 1
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