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96 Holiday homes in Siena Province

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96 Results  |  
11 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

1 night min stay

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from £51 /night

£356 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Immerso nella meravigliosa campagna toscana LA DOLCE VITA è un affittacamere all'interno di un antico casolare ristrutturato, circondato dall'atmosfera magica della natura incontaminata.  …see more

20 Photos

House | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £41 /night

£281 - £456 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Sun in summer, snow in winter, hiking, culture and charm of nature nothing is missing for a wonderful holiday in the comfortable house Contignano. The price is guaranteed. There are no additional charges. Utilities are included in the price.  …see more

17 Photos

House | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £87 /night

£605 - £894 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Belsedere is located on the top of a hill, near Pienza, Montepulciano, Cortona, Monte Oliveto Maggiore, Siena. There are four apartments, which overlook the garden of the villa or the grove of oaks beside the pool. Breakfast included. During the high season we offer a Sunday evening dinner guests of the farm.  …see more

Featured properties

14 Photos

House | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £82 /night

£570 - £701 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
Typical house in the heart of Siena's countryside,suitable for vacations from Spring to late October; come and discover the true pleasure of a vacation in Tuscany -150 euro damage deposit to be paid cash upon arrival -Internet conn. on request 6€ per 3GB or 20€ for 10GB  …see more

10 Photos

House | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £142 /night

£992 - £1323 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Make Stomemmano the destination, not just the base for your Tuscan holiday!  …see more

11 Photos

House | 2 Bedrooms | sleeps 7

3 Nights min stay

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from £62 /night

£430 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Extraordinary typical tuscan historic eighteenth-century residence, all restored, all high standard confort, located on a hilltop in the Siena countryside, in the charming medieval village Sinalunga. You will love your holidays there! Come and live the tuscan way of life : relaxing, friendly, refined.  …see more

8 Photos

House | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £296 /night

£2067 - £2728 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for over 5s only
  • Car advised
  • May take pets – please enquire
If you are searching for something very special, with charm, history and love for details- thats the place to be. It it the perfect hub to discover the jewels of tuscany (if you want to stay in lovely apartments with your friends) or to celebrate a ferry tale wedding-  …see more

24 Photos

House | 13 Bedrooms | sleeps 36

Very Good 4/5 

2 Nights min stay

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from £472 /night

£3300 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
On the sweet hills of the Chianti shire between vineyardand and olive groves, stands the "Podere il Pino". It offers a spectacular view on the beautiful medieval village of San Gimignano and it is very close to art cities as Florence, Siena, Pisa, Volterra and the sea.  …see more

24 Photos

House | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £56 /night

£386 - £877 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
The accommodation is very comfortable and well equipped.There are several tables and chairs outside where one can enjoy a meal and glass of wine watching the stunning view until darkness falls then watching the fireflies float around as you appreciate the calm serenity  …see more

24 Photos

House | 1 Bedroom | sleeps 5

Very Good 4/5 

3 Nights min stay

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from £50 /night

£348 - £538 / week

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Key info:

  • Nearest beach 50 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Tuscany, near Siena. Lovely small villa in the beautiful countryside, with large garden, veranda and private pool. Ideal for a relaxing holiday in full nature as well as for interesting visits to the sites of art in the area. The house is really cosy, situated in a very central and tranquil location. Siena is only 20 min. drive.  …see more

9 Photos

House | 2 Bedrooms | sleeps 4

Min stay varies

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from £95 /night

£662 - £992 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
3-room house 90 m2, on the ground floor, very tasteful furnishings: 1 room with 2 beds. 1 double bedroom with with corner bath.  …see more

20 Photos

House | 4 Bedrooms | sleeps 5

Very Good 4/5 

7 Nights min stay

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from £89 /night

£622 - £1288 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
CASALTA di PESA: Beautiful stone Tuscan hamlet in the splendid Chianti Classico vineyards. This property still shows the blazon of the astronomer Galileo Galilei who stayed in this hamlet many years and drew inspiration from the beauties of the surrounding landscape. Casalta di Pesa is an Holiday Home surrounded by vineyards, just outside Castellina in Chianti  …see more

14 Photos

House | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £83 /night

£575 - £1153 / week

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Late Deal: save up to €372 (approx. £307)

Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
This is a beautiful traditional stone house completely refurbished over two years ago. As a result the fit out is of a very high quality.Located on a hill overlooking a Unesco world heritage site with wonduferfu; views and sunsets to take home.  …see more

10 Photos

House | 1 Bedroom | sleeps 3

Short stays welcome

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from £53 /night

£371 - £446 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Tuscany, self catering, holiday let, Italy, romantic holiday, honey moon, casale  …see more

15 Photos

House | 1 Bedroom | sleeps 3

1 night min stay

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from £44 /night

£307 - £587 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
The apartment is located just 5 minutes drive from the walls surrounding the old town (10 min by bus) and its location also allows you to quickly reach the surroundings of the Sienese countryside. Supermarket and shops nearby. Being a one bedroom apartment of about 45 square meters, is ideal for 2 people, maximum of 3.  …see more

16 Photos

House | 2 Bedrooms | sleeps 6

Short stays welcome

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from £83 /night

£575 - £1153 / week

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Late Deal: save up to €372 (approx. £307)

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Beautiful newly restored two bedroom house with large kitchen, living room, garden and a swimming pool. Incredible unbroken 360 views over the Val D'Orcia valley. Sun-baked stone walls hand made terracotta floors, chestnut beams, pergolas twisted with wisteria. Located in the Val d'Orcia region south of Siena.  …see more

20 Photos

House | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £141 /night

£982 - £1840 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Self-catering holiday house in the heart of Tuscany, private swimming pool, quiet place with stunning panoramic view . Holiday house is ideal for families, groups seeking relaxation, romantic gateway. No smoking vacation house, near Siena. Pet friendly rentals. Dream holiday with private swimming pool and garden, quiet area with beutiful views of the Tuscan country  …see more

24 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

5 Nights min stay

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from £83 /night

£575 - £880 / week

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Key info:

  • Nearest beach 55 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Beautifully restored 16th century Granary building; stunning views of the Tuscan hills. Perfect for a romantic holiday; explore the best Tuscany has to offer or a family getaway. Gorgeous pool area and large private garden. Easy access to Florence, Pisa and Siena. The house has been tastefully renovated and is equipped to a very high standard throughout.  …see more

19 Photos

House | 1 Bedroom | sleeps 4

Short stays welcome

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from £38 /night

£263 - £439 / week

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Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
The apartment is situated in a residence which rapresent the perfect tuscan style. Centuries ago it was a convent, then it was inhabitated by farmers. It's the perfect place where you can spend your holidays in tranquility and relax, inside the typical Tuscan country.  …see more

17 Photos

House | 2 Bedrooms | sleeps 3

Excellent 5/5 

7 Nights min stay

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from £69 /night

£482 / week

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Key info:

  • Nearest beach 95 km
  • Suitable for over 5s only
  • Car not necessary
  • Pets welcome
Il palio di Siena, Firenze, Lucca, Val d'Orcia, Montalcino, Pienza, Bagno Vignoni, Montepulciano Private parking and bus stop for the center right in front of the villa!  …see more

14 Photos

House | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £418 /night

£2920 - £3963 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Walk to the local restaurants & grocery store or drive a short distance to numerous historical towns, but still enjoy the privacy & beautiful scenery of Tuscany. Dine 'al-fresco' under the vine-draped pergola & swim in the pool that looks out upon a timeless landscape. If you desire privacy with convenience; scenic views without isolation, Casa Oliveto is for you!  …see more

13 Photos

House | 5 Bedrooms | sleeps 14

Very Good 4/5 

Short stays welcome

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from £83 /night

£575 - £1236 / week

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Late Deal: save up to €372 (approx. £307)

Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Located on a hill overlooking the Val D'Orcia Tuscany's only Unesco heritage site is truly beautiful. A stay here will relax body and mind. We now offer excellent home cooked food within your house in the traditional tuscan style and cater for large or small groups.  …see more

24 Photos

House | 3 Bedrooms | sleeps 8

7 Nights min stay

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from £83 /night

£579 - £1240 / week

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Key info:

  • Nearest beach 50 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Charming Tuscany villa with private pool & garden. Ideal for families  …see more

19 Photos

House | 2 Bedrooms | sleeps 6

2 Nights min stay

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from £166 /night

£1157 - £1836 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
All the charm and comfort for an artistic stay in the heart of Tuscany. Montalcino has remained quite untouched and therefore has kept it's charming atmosphere. Moreover, if you love food and wine, especially Brunello, you cannot go wrong around here, come and enjoy!  …see more

13 Photos

House | 3 Bedrooms | sleeps 8

Short stays welcome

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from £118 /night

£823 - £1484 / week

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Late Deal: save up to €750 (approx. £620)

Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Beautiful Three bedroom stone house spread over three floors with the master bedroom on the top floor entered by a spiral staricase. Fully fitted kitchen with fridge freezr, dishwasher, oven and hob with all of the cooking equipment supplied.  …see more

24 Photos

House | 5 Bedrooms | sleeps 10

Excellent 5/5 

3 Nights min stay

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from £188 /night

£1315 - £1972 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
- In Valdichiana senese only a few kilometres from: Pienza,Montepulciano,Montalcino,Cortona,Siena, Arezzo and Perugia. - holidays in unique countryside, ancient cities, exquisite works of art and delicious food! - swming pool only for your exclusive use  …see more

22 Photos

House | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £126 /night

£877 - £1315 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Podere campana is a small organic farm located on a delightful hill surrounded by olive groves and vineyards, iPodere campana is a small organic farm located on a delightful hill surrounded by olive groves and vineyards, in the heart of the Valdichiana senese.  …see more

20 Photos

House | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £84 /night

£587 - £877 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Podere campana (www.poderecampana.it) is a small organic farm located on a delightful hill surrounded by olive groves and vineyards, in the heart of the Valdichiana senese.  …see more

24 Photos

House | 1 Bedroom | sleeps 3

Min stay varies

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from £51 /night

£351 - £701 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
The house, composed of 5 delightful apartments, has as it's main objective the idea of offering guests the opportunity to enjoy the calm, the beauty and all the pleasures our region has to offer. Our apartments have been renovated with respect for tradition.  …see more

13 Photos

House | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £101 /night

£701 - £1052 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Very confortable countryhouse, in the heart of Chianti hills, ideal for family or groups who wants to visit the best of Tuscany and relax in the country. Four large bedrooms, two bathrooms, large livingroom with fireplace, kitchen, big garden, internet wifi.  …see more

20 Photos

House | 2 Bedrooms | sleeps 4

1 night min stay

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from £182 /night

£1270 - £1550 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Emide D is a graceful apartment in a history-rich eighteenth-century estate. It sleeps four people. From Casa Emide D you will enjoy a marvelous view of the greenery. Casa Emide D is 80 square meters (860 square feet)  …see more

20 Photos

House | 3 Bedrooms | sleeps 8

1 night min stay

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from £93 /night

£645 - £1009 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Saveria E is a 100-square-meter (1076 square feet) house on a hill which sleeps eight people. It features a private patio and shared garden and swimming-pool. It is part of a small medieval hamlet consisting of stone houses restored as vacation homes  …see more

20 Photos

House | 1 Bedroom | sleeps 5

1 night min stay

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from £100 /night

£700 - £1100 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Casa Adalmina D is a pleasant and spacious apartment that is part of an ancient country house built on a hillside, surrounded by meadows and woods. It sleeps five people. From Casa Adalmina D you will enjoy an enchanting view of the Senesi hills  …see more

20 Photos

House | 2 Bedrooms | sleeps 6

1 night min stay

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from £75 /night

£521 - £786 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Saveria O is a gracious 60-square-meter (about 646 square feet) house on a hill which sleeps six people. It features a private terrace and shared garden and swimming-pool  …see more

20 Photos

House | 2 Bedrooms | sleeps 4

1 night min stay

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from £129 /night

£900 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Villa Diora C is a characteristic and welcoming apartment that is part of a villa surrounded by vineyards and olive groves. It sleeps four people. From Villa Diora C you will enjoy an enchanting view of the Tuscan hills and of the Chianti valley  …see more

20 Photos

House | 1 Bedroom | sleeps 4

1 night min stay

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from £70 /night

£490 - £800 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Casa Adalmina C is a pleasant and spacious apartment that is part of an ancient country house built on a hillside, surrounded by meadows and woods. It sleeps four people. From Casa Adalmina C you will enjoy an enchanting view of the Senesi hills  …see more

20 Photos

House | 2 Bedrooms | sleeps 5

1 night min stay

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from £100 /night

£700 - £1100 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Casa Adalberto D is a pleasant and spacious apartment that is part of an ancient country house built on a hillside, surrounded by meadows and woods. It sleeps five people. From Casa Adalberto D you will enjoy an enchanting view of the Senesi hills  …see more

20 Photos

House | 1 Bedroom | sleeps 5

1 night min stay

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from £100 /night

£700 - £1100 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Casa Adalberto B is a pleasant and spacious two-story apartment that is part of an ancient country house built on a hillside, surrounded by meadows and woods. It sleeps five people. From Casa Adalberto B you will enjoy an enchanting view of the Senesi hills  …see more

20 Photos

House | 2 Bedrooms | sleeps 6

1 night min stay

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from £75 /night

£521 - £786 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Saveria G is a gracious 60-square-meter (about 646 square feet) house on a hill which sleeps six people. It features a private patio and shared garden and swimming-pool  …see more

20 Photos

House | 4 Bedrooms | sleeps 7

1 night min stay

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from £550 /night

£3850 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Villa Diora A is a splendid sixteenth-century two-story apartment that is part of a villa situated in the heart of the Tuscan countryside. It sleeps seven people. From Villa Diora A you will enjoy an enchanting view of the Chianti hills and of the vineyards  …see more

20 Photos

House | 1 Bedroom | sleeps 4

1 night min stay

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from £70 /night

£490 - £800 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Casa Adalmina A is a pleasant and spacious apartment that is part of an ancient country house built on a hillside, surrounded by meadows and woods. It sleeps four people. From Casa Adalmina A you will enjoy an enchanting view of the Senesi hills  …see more

20 Photos

House | 6 Bedrooms | sleeps 15

1 night min stay

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from £215 /night

£1500 - £2700 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Villa Calatea is a characteristic three-story age-old farm house with strong character, which derives from it actually being restored from an old kiln. It sleeps 15 people. From Villa Calatea you will enjoy a splendid view of the Senesi hills and of the vineyards  …see more

20 Photos

House | 2 Bedrooms | sleeps 4

1 night min stay

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from £82 /night

£571 - £1116 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Giobatta T is a 110 square meter (approximately 1180 square feet) house in the countryside for four people, with a private patio and shared swimming pool, tennis court and garden  …see more

20 Photos

House | 3 Bedrooms | sleeps 6

1 night min stay

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from £182 /night

£1270 - £1670 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Villa Arnica A is a characteristic and welcoming ancient tuscan country house surrounded by vineyards and olive groves. It sleeps six people. From Villa Arnica A you will enjoy a charming view of the Chianti hills  …see more

20 Photos

House | 2 Bedrooms | sleeps 5

1 night min stay

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from £100 /night

£700 - £1100 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Casa Adalberto C is a pleasant and spacious apartment that is part of an ancient country house built on a hillside, surrounded by meadows and woods. It sleeps five people. From Casa Adalberto C you will enjoy an enchanting view of the Senesi hills  …see more

20 Photos

House | 3 Bedrooms | sleeps 9

1 night min stay

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from £130 /night

£910 - £1400 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Casa Adalberto A is a pleasant and spacious two-story apartment that is part of an ancient country house built on a hillside, surrounded by meadows and woods. It sleeps nine people. From Casa Adalberto A you will enjoy an enchanting view of the Senesi hills  …see more

24 Photos

House | 2 Bedrooms | sleeps 4

1 night min stay

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from £106 /night

£740 - £992 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Appartamento Il Riccio A is a romantic and welcoming two-story apartment surrounded by vineyards and olive groves. It sleeps four people. From Appartamento Il Riccio A you will enjoy an enchanting view of the Tuscan countryside and of the towers of San Gimignano  …see more

20 Photos

House | 2 Bedrooms | sleeps 6

1 night min stay

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from £122 /night

£850 - £1220 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Villino Gelia is a splendid two-story age-old farm house surrounded by meadows and by green hills. It sleeps six people. From Villino Gelia you will enjoy a breathtaking view of the Senesi hills and of the greenery. Villino Gelia is 90 square meters (970 square feet)  …see more

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House | 1 Bedroom | sleeps 2

1 night min stay

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from £55 /night

£381 - £587 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Saveria N is a gracious 40-square-meter (about 430.5 square feet) house on a hill which sleeps two people. It features a private terrace and shared garden and swimming-pool  …see more

20 Photos

House | 2 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £70 /night

£484 - £761 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Saveria I is a gracious 60-square-meter (about 646 square feet) house on a hill which sleeps six people. It features a private terrace and shared garden and swimming-pool  …see more