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Siena Holiday Rentals with Pools

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    Travellers to Siena are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    170 Matching Rentals in SienaView all 401 rentals
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    Exclusive Tuscan Villa with pool,hot tub,A/C,5 bd, free wi-fi,15 km from Siena1 / 222
    (51)Excellent
    5 Bedrooms, 7 Bathrooms, Sleeps 12 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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    Independent villa with private pool in Siena countryside - 3 bedrooms1 / 52
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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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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    Amenities & Details
    • 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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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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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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    Location Information
    53018, Siena, Province of Siena
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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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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    • 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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    53100, Siena, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, 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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    Amenities & Details
    • 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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    56041, Siena, Province of Siena
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 7
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    Apartment Camilla, countryside, not far from Siena1 / 17
    (6)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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    53018, Siena, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Bright, spacious villa with pool near Siena1 / 39
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 June 2017
    Could not have been more perfect!Spacious, comfortable and location was ideal, as close to all main attractions, although still had a country feel.Pool area was wonderful...
    Reviewed 1 April 2016
    We have been there in October 2015 and it was a lovely journey. The house has 3 bedrooms and 2 bathrooms. The surrounding is really beautiful and it's about 5 min from the...
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    About this property
    Key points: large apartment (140 m2) in a farmhouse renovated with taste and attention to details. Terrace and independent entrance into the courtyard of the property, large pool with view and garden-park with olive grove. Fully equipped kitchen, comfortable living room, bedrooms with exposed...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Castello di Montalto - 3 Bedroom Villa in Chianti1 / 38
    (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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    Il piccolo ulivo1 / 20
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    SIENA,villa,pool,tennis,relax,near Piazza IL CAMPO1 / 29
    (7)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
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 22 July 2017
    We have just returned today from the beautiful Siena! The villa "Le Tortore" is beautiful, clean and perfect for our week away. We went with our two children who adored...
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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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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    TuscanFlat1 / 72
    (17)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 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...
    Reviewed 13 June 2018
    Siena and Tuscan Flat was our third stop of four in the country. The view was, as stated before practically aerial and almost magical. Hearing the cathedral bells chime and the...
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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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • 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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    Private Villa,Pool, Hot tub,A/C,WiFi,5BR,15km from Siena1 / 67
    (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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    53100, Siena, Province of Siena
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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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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    53014, Siena, Province of Siena
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 20
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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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    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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    Location Information
    53018, Siena, Province of Siena
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 13
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    Authentic large 4BR farmhouse with  community pool between siena + florence1 / 74
    (13)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Shared Indoor Pool
    • DVD Player
    • Washer
    • Sauna
    • Patio
    • Central Heating
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 7 July 2015
    We spent a lovely week in Casa Pineta, our home for a week of travels in Tuscany. Conveniently located for many day trips, the house is large, with a well equipped kitchen. The...
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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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    Bellaria villetta con piscina e giardino1 / 44
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 6 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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    53100, Siena, Province of Siena
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53041, Isola d'Arbia, Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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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    Location Information
    53014, Siena, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Beautiful  tuscan Villa not far from Siena 18 pax1 / 22
    (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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    Location Information
    53018, Siena, Province of Siena
    Holiday Rental House - 9 Bedrooms, 9 Bathrooms, Sleeps 18
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    accogliente agriturismo1 / 29
    (11)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Wi-Fi
    • Private Garden
    • Grill
    • Cable/satellite TV
    • Central Heating
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53018, Costalpino, Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    Monterzi 41 / 40
    (7)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 1 week ago
    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...
    Reviewed 15 October 2017
    I wanted to treat my wife to something special for our 25th Wedding anniversary so after weeks and weeks of research selected Monterzi 4 in Montisi. I was looking for romantic...
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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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    11 Bedrooms, 11 Bathrooms, Sleeps 22 Quick View
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    • Private Outdoor Pool (Unheated)
    • Central Heating
    • Grill
    • Wi-Fi
    • DVD Player
    • Outdoor Dining Area
    • Secure Parking
    • 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
    Holiday Rental House - 11 Bedrooms, 11 Bathrooms, Sleeps 22
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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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Central Heating
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53041, Isola d'Arbia, Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Villa Luna1 / 32
    (17)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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    Location Information
    53019, Siena, Province of Siena
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 9
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    Stunning Villa in Siena with exclusive spa1 / 24
    (4)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Sauna
    • Washer
    • Private Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2017
    The house absolutely exceeded our expectations. Extremely charming and clean home in a great location. We were an extended family of 8 ages ranging from 10 to 80 and everybody...
    Reviewed 25 May 2017
    If you are looking for peace and beauty, and the feel of home, this is your spot! You could not find a warmer more helpful host than Marco. He is delightful. The home is so...
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    About this property
    This beautiful villa in Siena with private Spa-Wellness Center room is situated on the hills with a breathtaking view over the vineyards up to Siena. An ideal accommodation for all those seeking peace and quiet but also a perfect point of departure for visiting the beautiful attractions of the...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 10
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    Tuscan Villa with pool and garden front of Siena1 / 20
    (1)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Grill
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Parking
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 November 2017
    The location of these 2 Villas, Sol and Luna are definitely out in the country so it's rather remote. We stayed in the villa Luna which was clean although a bit spartan when it...
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    About this property
    Elegant villa on the hills of Siena of 170 square meters with garden and pool, furnished with fine furniture. Towering over the city, surrounded by greenery, in absolute peace and privacy, a few steps from the center, close to services pubblici.La villa on one floor with garden and pool sleeps up...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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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    Tuscany Villa with pool - Villa le Capanne holday in private villas1 / 96
    (65)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Washer
    • Cable/satellite TV
    • Central Heating
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Hot Tub
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Lovely Tuscan villa with a beautiful pool / hot tub area. Gina & Franco were fantastic hosts who left us the best welcome basket we have ever seen and continued to pamper...
    Reviewed 4 weeks ago
    Villa Le Capanne is truly a wonderful holiday experience. A wonderful home with every single thing catered for. A rural tranquil place to escape from it all but well located to...
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    About this property
    Villa with private pool located in Tuscany near Siena and Volterra. This private tuscan villa has been recently renovated in rustic style. Villa le Capanne is particularly suitable for those who love nature, privacy and relax. From the villa you can enjoy beautiful sunsets! The holiday Villa is...
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    Location Information
    56041, Siena, Province of Siena
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Casa Vacanze L'Oliveta1 / 24
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Parking
    • Washer
    • Air Conditioning
    • Outdoor Dining Area
    • Wi-Fi
    • Shared Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53100, Siena, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Casa Vacanze L'Oliveta1 / 38
    (1)Average
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Grill
    • Outdoor Dining Area
    • Washer
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 June 2018
    We enjoyed the spacious rooms and backyard patio and pool, the house however is on a busy street and can be a little noisy. The staff is friendly and tried their best to be...
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    53100, Siena, Province of Siena
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Apartment in Historic Farmhouse with pool1 / 27
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Balcony
    • Parking
    • Grill
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 October 2017
    Everything about Le Muricce was wonderful. It is a beautiful villa in a perfect location. Easy to get to Siena, Volterra, San Gimignano, Greve and many other places in Tuscany...
    Reviewed 26 July 2016
    Beautiful views all around. Very convenient to Siena and the countryside. Host very flexible as we were there during off season. Kitchen was well stocked. Shower stall was...
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    About this property
    The apartment (80m2) is on two floors. The entrance is on the ground floor through a glassdoor. The main room include a living area with a double sofa bed, a fully equipped kitchen and dining table, all renewed on January 2014. The bathroom is equipped with shower cabin. Single bed situated at the...
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    Location Information
    53035, Siena, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1000 year old Villa in a Nature Reserve1 / 21
    (50)Excellent
    8 Bedrooms, 8 Bathrooms, Sleeps 18 Quick View
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    • Air Conditioning
    • Balcony
    • Patio
    • Grill
    • Mountain Views
    • Washer
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 July 2018
    I can’t say enough about our week at Villa Montecastelli. Jens and his family and staff along with Amie made sure our every wish was granted. Every meal was spectacular, every...
    Reviewed 6 August 2016
    One of our best vacations ever! Stress free and tons of fun. Every day a different , wonderful adventure! Jens, the villa owner and our host is one of the most fascinating and...
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    About this property
    Montecastelli offers Villa accommodation for those seeking a hidden vacation rental. The Villa Montecastello has been restored with every attention to detail and history. Only an hour from the Florence airport and 20 minutes from Siena, Montecastelli nestles at the foot of the Montagnola nature...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 18
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    Picturesque Tuscan Villa near Siena Private Fenced Saline Pool Wi-Fi Pony 20P1 / 47
    (1)Excellent
    8 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2017
    A beautiful family-friendly Tuscan home with 3 separate apartments with everything you need and more, so you can enjoy your friends and family but have some privacy too. The...
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    About this property
    Entire Renovated Tuscan Stone Farmhouse with sleeps up to 20 people, 8 bedrooms of witch two with airconditioning, 7 bathrooms, private fenced chlorine-free pool (5 x 10), wi-fi, pizza oven, barbecue, pingpong, Beach Volley- and Football Field, childrens playground and pony. THE PROPERTY IS FOR...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 20
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    Private Tuscany Villa Centopino with pool jacuzzi for honeymoon & summer holiday1 / 21
    (10)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Housekeeping Included
    • Cable/satellite TV
    • Washer
    • Central Heating
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2018
    We often travel in Tuscany, in this villa we spent our honeymoon 5 years ago, we decided to stay in this country villa again and we had a great time. The private villa and the...
    Reviewed 6 August 2018
    After the birth of Giulia we decided to return to Tuscany in that beautiful villa where we spent part of our honeymoon. We were happy to find that the villa had even improved on...
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    About this property
    Private villa with swimming pool and jacuzzi ideal for those love nature and privacy and at the same time they love to visit the art cities of Tuscany, the Villa Centopino is located between Siena, Volterra and Florence. The villa furnished in rustic style has a large lawn around the pool,...
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    Location Information
    56040, Siena, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Abbadia di Siena1 / 31
    (2)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Parking
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 September 2016
    Delightful villa and fabulous swimming pool. Ideal for large family. Very close to Siena, so perfect base for exploring both the city and the countryside. Helpful, charming hosts.
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    About this property
    Abbadia di Siena is a large residence on two floors, capable of holding up to 7 persons with 3 double bedrooms and a single sofa bed in a study. It has 3 complete bathrooms, air conditioning in the living room and in the kitchen, Wi-Fi in the living room and on the terrace. Guests can also use the...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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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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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 3 Bedrooms, 3 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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    About this property
    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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    Tuscan villa on a hill with views of Siena1 / 102
    (1)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Wi-Fi
    • Balcony
    • Terrace
    • Cable/satellite TV
    • Grill
    • Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 June 2017
    Great place for a family. Lots of room, swimming pool. We enjoyed our stay. The owners let us stay in the yard & use the swimming pool the 5 hrs after check out while waiting...
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    About this property
    Explore the amazing hills of Siena: stay in VillaToscana of 240 sqm with garden and pool, which offers an exceptional view of the Chianti countryside, in absolute peace and privacy, a few steps from the center of Siena. The villa is on two floors can accommodate 10 people, it has four bedrooms a...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The villa lies in the hills of southern Tuscany (with a beautiful panorama) around 3 Kms from Radicofani. It forms an ideal starting point for enjoying the peace of the surrounding hills and on the other hand making trips by car (the highway A1 Florence-Rome is 25 Kms far away) to sparkling towns...
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    Location Information
    53040, Siena, Province of Siena
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Private Garden
    • Washer
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is part of an ancient monastery of the 13th century became a rural house the apartment is located on a hill facing Siena and is surrounded by countryside. Furnished and well equipped, it has a garden shared with other appartamenti. The apartment is located on the first floor of the rural...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    • Patio
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PRIVATE STRUCTURE. Alborata is an old Tuscan farmhouse entirely built in stone, dating to the beginning of the last century and situated not far from the village of San Giovanni d’Asso, in the unmistakable and characteristic countryside of the Crete Senesi. During the recent, careful renovation...
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Cable/satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 9
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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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    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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    Location Information
    53100, Siena, Province of Siena
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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