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Holiday Rentals with Pools in Siena

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    Travellers to Siena are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    167 Matching Rentals in SienaView all 386 rentals
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    Abbadia di Siena1 / 31
    (2)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Independent villa with private pool in Siena countryside - 3 bedrooms1 / 54
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Borgo dei Fondi - Il Forno ground floor1 / 16
    (9)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    TuscanFlat1 / 18
    (18)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • 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 22 September 2018
    Right in the heart of Siena with a 360 degree view of the city. Sitting on the terrace with a bottle of wine and some nice bread and cheese makes you almost too lazy to explore...
    Reviewed 28 July 2018
    We had a lovely stay in this flat in Siena. It is very clean, comfortable and well equipped and is in a superb location - within easy walking distance of all the sights. There...
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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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    Exclusive Tuscan Villa with pool,hot tub,A/C,5 bd, free wi-fi,15 km from Siena1 / 112
    (51)Excellent
    5 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 July 2018
    We were a group of four couples staying here for a week in June. My husband and I have stayed in rental properties all over Europe and the U.S. and this may have been the best...
    Reviewed 27 June 2018
    Our family group of 9, ranging in age from 8 to 72, was indeed fortunate to have stayed in this beautiful villa for 2 weeks. I researched vacation rentals in Tuscany for months...
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    About this property
    OUR LAST MINUTE SPECIAL OFFER : - BEST RATES ON MAY! - OVER 30% DISCOUNT ON WEEKLY RATES ALL YEAR!! - OUR RATES ARE PROUNDLY ALL INCLUDED....no extra expenses,no final cleanings, no damage deposit, city tax included, the rate you see it's what you will pay! ALL PROPERTY IS FOR YOUR EXCLUSIVE USE...
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    53018, Siena, Province of Siena
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 12
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    OUR LAST MINUTE SPECIAL OFFER : - BEST RATES ON MAY! - OVER 30% DISCOUNT ON WEEKLY RATES ALL YEAR!! - OUR RATES ARE PROUNDLY ALL INCLUDED....no extra expenses,no final cleanings, no damage deposit, city tax included, the rate you see it's what you will pay! ALL PROPERTY IS FOR YOUR EXCLUSIVE USE...
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    53018, Siena, Province of Siena
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    SIENA,villa,pool,tennis,relax,near Piazza IL CAMPO1 / 33
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 September 2018
    We had a brilliant two week stay in this lovely villa. It was away from it all in a gated estate but yet only a 20 minute walk into the centre of Siena. The pool was beautiful...
    Reviewed 21 August 2017
    We have stayed on this gated estate many times over the past forty years. Its location just outside the city walls with views over the Tuscan countryside, but within 15 minutes...
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    About this property
    La villa (5 posti letto ) è situata nella campagna di Siena a circa 15 minuti a piedi dalla famosa 'Piazza del Campo' di Siena. Si trova in cima ad una collina, corredata di piscina e campo da tennis, offre splendidi panorami sulla città e sulla campagna circostante. È immersa nel verde di una...
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    53100, Siena, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Villa with Pool and Jacuzzi private Deal 20191 / 25
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Central Heating
    • Hot Tub
    • DVD Player
    • Grill
    • Balcony
    • Housekeeping Included
    • Washer
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2017
    Fantastic villa, located down a private road with fabulous views and no near neighbours. The owners have made this a "home from home" and have thought of everything to...
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    About this property
    A private villa with pool and jacuzzi 115sqm situated at the center of Tuscany between Siena, Volterra, Pisa and Florence. Ideal Fo summer holiday or Honeymoon. Villa exclusive (you will not find other guests in the area) with a view of the pool and the Tuscan countryside, surrounded by greenery...
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    Location Information
    56041, Siena, Province of Siena
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 7
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    Abbadia di Siena 121 / 41
    (1)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Parking
    • Washer
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2018
    We hired this villa for a holiday with family and friends (10 adults). The villa was clean and comfortable with a lovely rustic homely feel and we all felt at home. There was...
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    About this property
    Abbadia di Siena 12 is a large residence on two floors, capable of holding up to 12 persons with 5 double bedrooms, an extra bed and a single sofa bed in a study. It has 4 complete bathrooms, air conditioning in the living room and in the kitchen, Wi-Fi in the living room and on the terrace. Guests...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Borgo dei Fondi -La Loggia-1 / 16
    (8)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Terrace
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 November 2017
    We stayed here four four nights during our trip to Tuscany. It was the perfect location to visit the nearby towns (including Siena) while enjoying the quiet setting of a...
    Reviewed 18 July 2015
    Just stayed 3 nights here. Weather was very hot which actually was the only issue as there was no air conditioning in our house. Other than that the facilities were very good...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Central Heating
    • Private Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Capannina was the former granary of this large estate situated in the Siena countryside. It has been totally renovated and transformed into a delightful holiday home for lovers of rural Tuscany. Located to the east of Siena, it is surrounded by large olive groves, vineyards and tilled fields....
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    53100, Siena, Province of Siena
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Authentic large 4BR farmhouse with  community pool between siena + florence1 / 37
    (14)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Shared Indoor Pool
    • DVD Player
    • Washer
    • Sauna
    • Patio
    • Central Heating
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 September 2018
    We were greeted on arrival by the charming son of Ulrike E. He showed us to our Villa and gave us a quick tour. There were starter goodies, coffee, tea, etc. Ulrike prepared a...
    Reviewed 28 September 2017
    The location was perfect. Only 1.3 miles from town ( Castellena ).Every restaurant was excellent. Easy access to all the Hill Towns of Tuscany.The owner was delightful and...
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    About this property
    'Casa Pineta' is part of the 76 ha large property of Poderi Val Verde and lies inbedded in 2 ha of parklike welcared gardens - The farmhouse offers the rare flair of an authentic Tuscan country home of more then 400 years , combined with modern comfort. More then 200 sqm offer plenty of space...
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    ITALY, Siena, Province of Siena
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    6 Bedrooms, 7 Bathrooms, Sleeps 13 Quick View
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    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Grill
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    OUR LAST MINUTE SPECIAL OFFER : - BEST RATES ON MAY! - OVER 30% DISCOUNT ON WEEKLY RATES ALL YEAR!! - OUR RATES ARE PROUNDLY ALL INCLUDED....no extra expenses,no final cleanings, no damage deposit, city tax included, the rate you see it's what you will pay! ALL PROPERTY IS FOR YOUR EXCLUSIVE USE...
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    53018, Siena, Province of Siena
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 13
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    Siena San Fabiano suite in farmhouse1 / 15
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Secure Parking
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Outdoor Dining Area
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2018
    My family of six recently stayed in two suites in san Fabiano in August. The place was perfect — clean spacious and the property is beautiful and all you could possibly want...
    Reviewed 10 September 2012
    We stayed here with our 3 kids, 10,12 and 16. They all had a wonderful time. There were many activities that they all enjoyed. The use of bikes was a hit. The swimming pool...
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    About this property
    beautiful climatized villa offers self catering suites with jacuzzi tubs, swimming pool,WI-FI,TV,mountain bikes, only 7 miles south of Siena.English speaking hosts! The Il Pino suites has beautiful views! Kosher accomodation can be offered upon request.
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    53014, Siena, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Wi-Fi
    • Outdoor Dining Area
    • Private Outdoor Pool (Unheated)
    • Patio
    • Grill
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Central Heating
    • Washer
    • Parking
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This farmhouse is situated on a large estate in the vicinity of a tiny hamlet in the countryside to the east of the city of Siena. It is surrounded by cultivated land in the form of large olive groves, vineyards and tilled fields: a broad and peaceful vista with Siena in the background. This is a...
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    53100, Siena, Province of Siena
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Grill
    • Washer
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    OUR LAST MINUTE SPECIAL OFFER : - BEST RATES ON MAY! - OVER 30% DISCOUNT ON WEEKLY RATES ALL YEAR!! - OUR RATES ARE PROUNDLY ALL INCLUDED....no extra expenses,no final cleanings, no damage deposit, city tax included, the rate you see it's what you will pay! ALL PROPERTY IS FOR YOUR EXCLUSIVE USE...
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    Location Information
    53018, Siena, Province of Siena
    Holiday Rental House - 4 Bedrooms, 7 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Typical stone farmhouse, originally an old barn, on three floors for a total area of 270 sq. m., holding up to 8 persons with 4 double bedrooms and three bathrooms. The villa is surrounded by a large garden with cypress and olive trees and a private swimming pool, as well as outdoor dining and...
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    53100, Siena, Province of Siena
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Podere Madonna di Mezzo 61 / 39
    (1)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Secure Parking
    • DVD Player
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2018
    We realised we would arrive earlier than we expected from Rome, and texted the local contact number to say we would arrive in about an hour. No response. We arrived at the villa...
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    About this property
    PRIVATE STRUCTURE. Villa Podere Madonna di Mezzo is a typical country style house, built in stone and brick and recently restored respecting it’s original design. Situated on a sweet rolling Tuscan hillside with a splendid views of the medieval hamlet of Cetona, and the enchanting landscape of the...
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    53100, Siena, Province of Siena
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Villa Del Cielo with Caminetto1 / 11
    (4)Very good
    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Private Garden
    • Parking
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2018
    We had a most wonderful week at Villa del Cielo (Villa Pace). The house was perfect for our three German, Norwegian and Australian families (6 adults and 7 children). The villa...
    Reviewed 1 March 2015
    This was our first time to rent a villa in the Tuscany region. We contacted Rent-A-Villa and spoke to Nicole, who is now a good friend. She took our needs and location and...
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    About this property
    Located just five kilometers from Siena, this villa offers an ideal combination of elegant simplicity and historical charm and comes complete with its own chapel, all which create a unique experience. Along with the private swimming pool, this holiday accommodation is nestled within the Tuscan...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    6 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Wi-Fi
    • Central Heating
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Montechiaro Capanna farmhouse is part of a large estate belonging to an ancient family situated in the countryside to the east of Siena. It is not isolated, since there is a small residential hamlet in the vicinity. Guests enjoy all-round panoramic views over the surrounding countryside of...
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    53100, Siena, Province of Siena
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 10
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    7 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • DVD Player
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    “Villa la Strega” dates back to the 18th century and has been refurbished recently keeping its sober Tuscan elegance. The view of the city that can be enjoyed from here is unique, an ideal choice for a group of friends who want to visit Siena alternating it with excursions to the more famous...
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    53100, Siena, Province of Siena
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 12
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    Apartment Camilla, countryside, not far from Siena1 / 17
    (8)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 5 October 2018
    Lovely apartment in a beautiful secluded spot and would have been perfect apart from one thing, the owner Franco. Unfortunately dispuite not living on site he was there nearly...
    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...
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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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    Villa Luna1 / 32
    (18)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Secure Parking
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 September 2017
    Choosing Villa Luna to stay at while in Siena was the right choice! I booked it in November last year and just returned from our stayed there with my sister and her husband and...
    Reviewed 22 August 2017
    We appreciated the service. Location is good as the breakfast. Our first room for the first night was pretty bad. Only a very small window near ceiling as basement, quite...
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    53019, Siena, Province of Siena
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 9
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    Siena San Fabiano  climatized villa with pool1 / 30
    (12)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • DVD Player
    • Grill
    • Patio
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 July 2018
    something for everyone from grandkids to grandparents. Great location, close to Sienna, 50minutes to Florence. Quaint little town short walk away. Hosts , and staff kind...
    Reviewed 1 October 2016
    San Fabiano is a great place to visit and have fun with your family. You've got everything you need for the young and old: sports facilities, specials sites to visit like Siena...
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    About this property
    the villa San Fabiano is located near Siena,in Tuscany. Beautifully restored, it has every amenity, including air conditioning. It can be rented entirely,sleeping up to 20 people, or separetly. It offers 4 self-catering suites, called Il Pino, il Forno, il Vino, il Pozzo, and an independent villa...
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    Location Information
    53014, Siena, Province of Siena
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 20
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    Castello di Montalto - 3 Bedroom Villa in Chianti1 / 19
    (3)Very good
    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 17 May 2018
    This is a special place with stunning views, more than a thousand years old, in the country but near Siena, in the Chianti wine region. The staff and the owner were most...
    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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    Podere Rota1 / 43
    (2)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Private Outdoor Pool (Heated)
    • Grill
    • Cable/satellite TV
    • Parking
    • Washer
    • Central Heating
    • Outdoor Dining Area
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53018, Siena, Province of Siena
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 11
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    9 Bedrooms, 9 Bathrooms, Sleeps 17 Quick View
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    • Wi-Fi
    • Washer
    • Grill
    • Air Conditioning
    • Mountain Views
    • Cable/satellite TV
    • DVD Player
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RECEPTIVE STRUCTURE. Il Poderuccio is a property merged into the Tuscan countryside, surrounded by the hills painted in beautiful golden and green. The house is 4 km only from the medieval town of Cetona, a centre famous among tourists in search of the a more authenthic Tuscany. Its size and...
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    53100, Siena, Province of Siena
    Holiday Rental House - 9 Bedrooms, 9 Bathrooms, Sleeps 17
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    Monterzi 41 / 40
    (8)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Mountain Views
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Grill
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 October 2018
    Hard to know where to start, we must have spent 2 month trying to find the ideal balance between seclusion & an easy stroll into a neighbouring town. Would you believe it...
    Reviewed 13 September 2018
    We loved this villa - it is furnished in the traditional Italian style which we like, the pool is spotless and the views are spectacular. It is within walking distance (10...
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    About this property
    PRIVATE STRUCTURE. The recent renovation of an old ruin, once used as stables, gave rise to Monterzi, a pretty farmhouse perched on top of a hill, in a discreet position in a property surrounded by vineyards and olive trees yet not far from the lively medieval borgo of Montisi, just a short,...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    agriturismo La torre di monsindoli1 / 28
    (14)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Shared Garden
    • Wi-Fi
    • Washer
    • Parking
    • Grill
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2016
    Our family of 4 had a lovely week staying in one of a small number of apartments in the Tuscan hills, only a few minutes drive from the outskirts of Siena. The setting was...
    Reviewed 29 October 2015
    Wow 13th century home minutes from Siena. Wonderful stay at a beautiful property. It was great to be away from people and just enjoy this beautiful part of Italy.the owner could...
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    53100, 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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    • 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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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Secure Parking
    • Private Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RECEPTIVE STRUCTURE. Podere San Giuseppe is a splendid farm immersed in the charming Tuscan hills halfway between Siena and Florence. The property, built in the last century, has been recently restored with great care by the owners keeping the original architecture but at the same time by adding...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    Rentals for 9 to 11 at Casina Dei Pini in Siena1 / 48
    (2)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • DVD Player
    • Grill
    • Private Outdoor Pool (Unheated)
    • Washer
    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 July 2014
    We did a lot of research before picking this villa and we are happy to say that we really enjoyed our stay at Casina dei Pini. The views were absolutely spectacular and the...
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    About this property
    PRIVATE STRUCTURE. Casina dei Pini is a country house dating back to 1860. It has been recently completely renovated and, in respect of the classical Tuscan tradition, ceilings with open-face beams and bricks have been retained whilst the floors and stairs have been lined with Tuscan travertine....
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 11
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Secure Parking
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RECEPTIVE STRUCTURE. Podere San Giuseppe is a splendid farm immersed in the charming Tuscan hills halfway between Siena and Florence. The property, built in the last century, has been recently restored with great care by the owners keeping the original architecture but at the same time by adding...
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    53100, Siena, Province of Siena
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Il piccolo ulivo1 / 20
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
    • Patio
    • Parking
    • Shared Indoor Pool
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53041, Siena, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Gated Luxury Estate “LaChiusa” Prime Chianti Classico! Exquisite Privacy & Views1 / 42
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Mountain Views
    • DVD Player
    • Housekeeping Included
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 October 2016
    The house was fantastic and the owner, Michael, was extremely helpful in the run up to the trip. His recommendations were spot on and the four of us had a lovely time staying...
    Reviewed 25 October 2016
    Such a beautiful location! The interior decoration was perfect as well. The back patio was very nice and there was lots of running around room for the kids! Different paths for...
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    About this property
    Appointed luxury in the Chianti Countryside! “LaChiusa” is the given name of this classic home. “LaChiusaChianti” near Siena and Florence. ~Set securely behind gates atop a private access road, enter a comfortable and superior-styled vacation home in the prime historic and most central area of...
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    Location Information
    53019, Siena, Province of Siena
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    Bellaria villetta con piscina e giardino1 / 42
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Grill
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2017
    The location of this beautiful Tuscan villa is amazing. The road towards the villa is very nice, once you reach the house you will find a beautiful Tuscan villa surrounded by...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Washer
    • Mountain Views
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PRIVATE STRUCTURE. Villa Ada is in the heart of the countryside of Sarteano, about 800 meters from the town centre in a reserve and panoramic position. The interiors of this splendid property have been chosen with style ensuring the original Tuscan style with wooden ceiling beams and “cotto”...
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    53100, Siena, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sferracavalli 41 / 32
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Mountain Views
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2016
    We thoroughly enjoyed our stay. The owners were incredibly kind and helpful. There were plenty of outdoor games for the kids. 2 minute drive from Sarteano where we discovered a...
    Reviewed 5 July 2015
    We have just returned from two weeks in this villa and it is absolutely lovely. We were met by Bruna and Suzanna who don't speak very much English and we speak very little...
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    RECEPTIVE STRUCTURE. Sferracavalli is a delightful little villa just outside Sarteano, a picturesque medieval borgo full of architectural masterpieces, located on the slopes of Mount Cetona south of Siena, between the southern Val di Chiana and the harsh and wild Val d'Orcia and very close to the...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Mountain Views
    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PRIVATE STRUCTURE. An old farmhouse dating back to the 19th century, La Pergola is today, thanks to careful restoration, an elegant country house, exquisitely inspired in its structure, with open-face stone and, indoors, the typical taste of Tuscan architectural tradition. Wood, terracotta, wrought...
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    Location Information
    53048, Siena, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    8 Bedrooms, 9 Bathrooms, Sleeps 16 Quick View
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • DVD Player
    • Mountain Views
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RECEPTIVE STRUCTURE. Podere San Giuseppe is a splendid farm immersed in the charming Tuscan hills halfway between Siena and Florence. The property, built in the last century, has been recently restored with great care by the owners keeping the original architecture but at the same time by adding...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 16
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    6 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Grill
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    OUR LAST MINUTE SPECIAL OFFERS : - BEST RATES ON MAY! - OVER 30% DISCOUNT ON WEEKLY RATES ALL YEAR!! - OUR RATES ARE PROUNDLY ALL INCLUDED....No extra expenses, No final cleanings, No damage deposit, city tax included, the rate you see it's what you will pay! YOUR DREAM VACATION IN TUSCANY BEGINS...
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    Location Information
    53018, Siena, Province of Siena
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 14
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    Apartment Valentina countryside not far from Siena1 / 19
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Central Heating
    • DVD Player
    • Parking
    • Outdoor Dining Area
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Renovated Tuscan Farm near Siena Private Fenced SalinePool Pizza oven Wi-Fi 16P1 / 49
    (1)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Patio
    • Mountain Views
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2018
    Liesbeth gave us full details on how to arrive to the place and how to move around the area. The house is a gorgeous Villa from 1300 A.D. . and it is surrounded by nature...
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    About this property
    Entire Renovated Tuscan Stone Farmhouse with sleeps up to 16 people, 6 bedrooms of witch two with airconditioning, 5 bathrooms, private fenced chlorine-free pool (5 x 10), wi-fi, pizza oven, barbecue, pingpong, pony, playground, Beach Volley- and Soccer Field. THE PROPERTY IS FOR YOUR EXCLUSIVE...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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    Private Villa,Pool, Hot tub,A/C,WiFi,5BR,15km from Siena1 / 68
    (6)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Hot Tub
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 December 2015
    I rented Le Caggia for a yoga retreat. The hosts, Jacopo & Fabio are simply amazing. They asked me to tell them what I wanted, offered suggestions, and then came up with an...
    Reviewed 5 August 2015
    From the beginning, when we decided to book this property everyone in our group felt in love with this home. Now I am so happy that we chose this Villa Our week there was...
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    About this property
    OUR LAST MINUTE SPECIAL OFFERS : - BEST RATES ON MAY! - OVER 30% DISCOUNT ON WEEKLY RATES ALL YEAR!! - OUR RATES ARE PROUNDLY ALL INCLUDED....No extra expenses, No final cleanings, No damage deposit, city tax included, the rate you see it's what you will pay! YOUR DREAM VACATION IN TUSCANY BEGINS...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    Beautiful  tuscan Villa not far from Siena 18 pax1 / 25
    (4)Excellent
    9 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Cable/satellite TV
    • Parking
    • Grill
    • Washer
    • Central Heating
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 June 2018
    We booked the whole villa for 3 nights in mid-May. We were a family group of 17 and were very comfortable in the 9 bedrooms in the 3 wings. The villa (built in 1840), is a...
    Reviewed 8 July 2012
    Very comfortable house with the necessary gadgets(dishwasher,2 washing machines,tv,a bathroom for each bedroom,table tennis etc., )very clean.The owners were very gentle people...
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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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    53018, Siena, Province of Siena
    Holiday Rental House - 9 Bedrooms, 9 Bathrooms, Sleeps 18
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    Santo Stefano 101 / 57
    (4)Very good
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 2014
    We spent most of the week May 12th, 2014. It is a fabulous villa with all kinds of choices, which bedroom will I sleep in, will I cook, or have Angela cook? Will I read or...
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    About this property
    RECEPTIVE STRUCTURE. Villa Santo Stefano is a splendid property situated in the Tuscan hillside, bordering the green heart of Umbria. This property, is built entirely in stone, and has been carefully and professionally restored respecting the functionality of the original architecture. Particular...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    Fortilizio 61 / 34
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 August 2018
    We stayed at this amazing villa at the end of July and loved every minute. The villa itself is well equipped with all the essentials including air conditioning, washing machine...
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    PRIVATE STRUCTURE. Fortilizio, situated at the edge of the town of Rapolano Terme, on a hilltop overlooking the Val di Chiana and the plain of the Sentino, and surrounded by woods of oak and chestnut trees, is an old watchtower, part of the larger complex of the 'Castellare di Sarri,' a...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    6 Bedrooms with Ensuite Baths, Pool, Wifi, Great Location1 / 63
    (10)Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Patio
    • Parking
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 September 2015
    This summer a group of 11 of us went to Tuscany. We stayed for a week at Villa Vetrichina and it is beyond beautiful. The grounds are so well kept and the home itself is...
    Reviewed 21 July 2015
    Patrizia/Villa Vetricina were wonderful. House, grounds, pool, view, Patrizia and family and friends left my family with cherished memories. Ten adults (5 couples) and we all...
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    About this property
    Beautiful Casa Patrizia. 6 bedrooms with queen-sized beds, all with ensuite baths. Plus another bedroom with two single beds -- so sleeping up to 12 (+2 children). Heated swimming pool, deluxe furnishings, air conditioning throughout, great location, this property has it all. Perfect for...
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    Location Information
    53040, Siena, Province of Siena
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A cypress tree lined road will lead you to Villa le Tortore and it represents a perfect introduction to this amazing Tuscany villa located just 15 minutes walking from Piazza del Campo, the very heart of Siena. From its privileged hilltop position it enjoys spectacular views over the countryside...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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