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694 Holiday homes in Province of Siena

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694 Results  |  
5 Photos

House | 1 Bedroom | sleeps 2

Good 3.5/5 

1 night min stay

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from £35 /night

£242 / week

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Key info:

  • Not suitable for children
  • Pets welcome
Piccola, accogliente, centrale e dotata di ogni comfort  …see more

20 Photos

Farmhouse | 7 Bedrooms | sleeps 14

Good 3.5/5 

1 night min stay

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from £65 /night

£452 / week

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Key info:

  • Nearest beach 65 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
Appartamenti,camere,ristorante tipico,piscina,cantina,Brunello di Montalcino,Val d'Orcia VENDITA DIRETTA DI TUTTI I NOSTRI PRODOTTI AGRICOLI (VINO-,OLIO EXTRAVERGINE DI OLIVA,GRAPPA,ACETO,ORTAGGI)  …see more

24 Photos

B&B | 1 Bedroom | sleeps 2

Good 3/5 

1 night min stay

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from £67 /night

£469 - £768 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
Un benessere che comincia dalle camere arredate con gusto e dotate di tutte quelle piccole comodità capaci di farvi sentire in vacanza e che prosegue con il piacere del palato con la cucina tipica ed anche Gluten Free della Taverna del Barbarossa antico casale del 1200 Camera Confort 16/18 mq : minibar tv satelittare cassaforte asciuga capelli, lato piscina e A/C su richiesta  …see more

Featured properties

9 Photos

Cottage | 1 Bedroom | sleeps 2

 

3 Nights min stay

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from £79 /night

£550 - £605 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Your own private house in Siena with a private garden, in a beautiful residential area of Siena. All the main sights of Siena are within walking distance, and the Piazza del Campo is just a short stroll away. The bus stop for Florence is not far from the house. An excellent choice to explore this historic city and retreat to a little oasis of calm after each jaunt.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

3 Nights min stay

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from £185 /night

£1291 - £1775 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Colletalli is an ideal location to recharge ones energy away from the humdrum of daily life conveniently located within 1 hour motoring of Florence, Siena, Sangimignano, Volterra, sandy beaches  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 21

3 Nights min stay

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from £260 /night

£1815 - £3392 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
This beautiful holiday home in the Val d'Orcia, surrounded by gently rolling hills, is near Castiglione d'Orcia (12km), just a few kilometres from the famous spa waters at Bagno Vignoni (10km) and Bagni San Filippo (7km). Surrounded by peace and quiet  …see more

23 Photos

Villa | 5 Bedrooms | sleeps 10

1 night min stay

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from £1049 /night

£7339 - £10081 / week

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Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Amazing villa,with pool and large garden close to Siena  …see more

22 Photos

Guest house | 1 Bedroom | sleeps 12

1 night min stay

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from £93 /night

£646 - £2134 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Come and enjoy a taste of authentic Tuscan country life in stunning settings, amidst olive groves and vineyards tendered by a most hospitable family who run this organic farm and live in your hosts' homestead or in newly refurbished independent apartments. Perfect for family and group of friends  …see more

23 Photos

Villa | 3 Bedrooms | sleeps 5

7 Nights min stay

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from £113 /night

£791 - £1017 / week

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Key info:

  • Great for children of all ages
  • Pets welcome
Podere Staggia is a splendid farm house (18 th century) located on the top of a hill. The apartment of this farmhouse offers you the unique and rare possibility to enjoy an old, large (170 m2) and luminous house in the Siena area with a 360° open view. Ideal place for a family or a group of friends to enjoy quiet and restful holidays.  …see more

24 Photos

Farmhouse | 10 Bedrooms | sleeps 20

Short stays welcome

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from £577 /night

£4033 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
The Wine Estate of Castelnuovo Tancredi has 3 stone farmhouses with a shared pool overlooking the gorgeous countryside, set in a private game reserve. Rent a farmhouse individually, or the entire property. Ideal for family reunions and weddings. You haven't seen the real Tuscany until you seen the Val d'Orcia. Wine tastings and cooking classes on site.  …see more

12 Photos

Villa | 8 Bedrooms | sleeps 25

7 Nights min stay

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from £93 /night

£646 - £2823 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Tuscany, Toscana, Casale, Piscina, Vigneto, Corsi cucina, Caccia al tartufo, Villa, Casa Vacanze, Italia, Equitazione, Matrimonio, matrimoni, eventi, lusso, Catering ;Tastings and Wine Tour's; Truffle Hunting ;Cooking Classes; Excursions; Horse Riding  …see more

17 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £553 /night

£3871 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Cosoli is located in Chianti Classico, conveniently half way from Florence and Siena. The villa overlooks a massive olive grove but yet surrounded by a great view of surrounding vineyards and small cities in the distance. 3 hours weekly housekeeping is included as well as the complete house cleaning after leaving.  …see more

10 Photos

Farmhouse | 4 Bedrooms | sleeps 16

2 Nights min stay

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from £346 /night

£2420 - £3226 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
The Podere Podernovo offers accomodation up to 16 people,with all comforts,as heating, air condititioning, Internet,wi-fi, Tv with Sky.The Count Fiorentini will welcome you in his farmhouse just 12 km south of Siena in the Arbia valley.  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 18

7 Nights min stay

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from £196 /night

£1371 - £4275 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Splendid villa with breathtaking view over the Castle of Strozzavolta, in the Chianti, between Florence and Siena.  …see more

18 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £265 /night

£1855 - £4597 / week

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Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
The villa is located 800 meters from a traditional Tuscan restaurant and four kilometers from the nearest village of Montepulciano where you'll find a few shops, restaurants, and a market. Nearby: Pienza, Montefollonico, Bagno Vignoni, Cortona, Orvieto, Castiglion del Lago, S.Quirico, Montalcino  …see more

25 Photos

House | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £116 /night

£807 - £1210 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great 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

24 Photos

Villa | 6 Bedrooms | sleeps 10

7 Nights min stay

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from £208 /night

£1452 - £2823 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Villa in Siena with SPA room, exclusive use.  …see more

10 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £73 /night

£509 - £968 / week

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Key info:

  • Nearest beach 100 km
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
We are situated in the historical heart of Tuscany and Chianti, half way between Siena and Firenze, on a hill overlooking a green and striking valley.The apartments are located in a picturesque hamlet that has been completely ristored- chianti full immersion, wine, food, striking landscape and culture  …see more

10 Photos

House | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £139 /night

£968 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Make Stomemmano the destination, not just the base for your Tuscan holiday!  …see more

20 Photos

Apartment | 4 Bedrooms | sleeps 9

1 night min stay

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from £138 /night

£960 - £1130 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
On the ground floor of a 1600 Villa ,completely renovated for the maximum comfort of guests. All windows facing the valley and the natural reserve below.50 square meter private terrace with incredible view on the countryside.15x4 meter swimming pool .  …see more

8 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £185 /night

£1291 - £2017 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Not far from Siena, for 5 minutes along the road from San Gimignano goes towards Gambassi, we find the gates of Villa Panorama. It is an old building of more than 5 centuries and tastefully decorated and with quality furniture and style typical of the villas in Tuscany  …see more

17 Photos

Apartment | 2 Bedrooms | sleeps 5

3 Nights min stay

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from £85 /night

£589 - £968 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
Beautiful holiday resort near Montepulciano and Pienza  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £104 /night

£726 - £4839 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Private Apartment in historic Villa with swimming pool, tennis court and 5 hectare garden. Near Siena, Montepulciano, Cortona etc. 4 bedrooms (or more if needed) with 2 bathrooms, 1 separate WC, 1 kitchen, 1 living room, private terrace and garden!  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

1 night min stay

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from £135 /night

£945 - £1700 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
The bedrooms are located on the first floor: a double bedroom with bathroom with shower, a twin-bedded room with bathroom with tub, a twin-bedded room with bathroom with shower.  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £75 /night

£525 - £888 / week

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Key info:

  • Nearest beach 70 km
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
An old Tuscan farmhouse nestled in a typical hilly tuscan landscape away from chaos and city traffic, but easy reachable. Swimming-pool, nice private gardens, solarium-terrace, fitness-room, barbecue-area, free wi-fi unlimited connection. The property is located very close to the characteristic medieval towns of San Gimignano and Volterra.  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £150 /night

£1049 - £1775 / week

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Key info:

  • Nearest beach 75 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Offers a unique view of the surrounding valley typical of the Sienese hills (olives and grapes) and is located a short distance (3 km) from the town of San Gimignano famous for its medieval towers.  …see more

9 Photos

House | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £182 /night

£1271 - £1920 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
The house has been well restored and decorated. Access is by external steps and a short flight of internal steps. With views stretching across the rolling hills, your afternoons will be spent by the spacious pool, set in the lovely scented garden.  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £93 /night

£646 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Il Pozzo is an apartment which is part of a converted farmhouse from the eighteenth-century, entirely in stone, that was recently the subject of a careful and passionate restoration. A park of three hectares surrounds the property. There is also a swimming pool on-site  …see more

21 Photos

Apartment | 4 Bedrooms | sleeps 9

1 night min stay

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from £185 /night

£1291 - £1492 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
A really charming and cosy mansard in the ancient stone villa Pian dell'Asso near Montalcino, Pienza, Siena, Montichiello. An enchanted garden and an amazing swimming pool with view on Montalcino for a relaxing holiday: good food and wine, art and sport.  …see more

12 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £143 /night

£1000 - £2936 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Villa with private garden and swimming pool on a hillside with views over beautiful countryside. Part of an old estate in the heart of the classic Tuscany. A wonderful place for a large family gathering, near Siena, Florence and the Tuscan hill towns nearby.  …see more

5 Photos

Apartment | 1 Bedroom | sleeps 2

4 Nights min stay

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from £85 /night

£595 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
A short walk from the Campo and the Duomo. Tastefully furnished, ideal for those who want to enjoy the town on foot, and its beautiful surroundings by bus. Panoramic views over Siena can be admired from the windows. Shops and restaurants within easy walking distance.  …see more

8 Photos

Apartment | 1 Bedroom | sleeps 3

Min stay varies

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from £55 /night

£380 - £440 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
An old stone farmhouse on the edge of a village. Restaurant close by. The friendly owners on site produce olive oil and Chianti. For those who want a simple rural property, a wonderful spot for walking and ideal base for exploring this beautiful part of Tuscany.  …see more

22 Photos

Apartment | 3 Bedrooms | sleeps 4

4 Nights min stay

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from £105 /night

£734 - £1291 / week

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Key info:

  • Nearest beach 75 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
"Casa Serena" is located in a panoramic position, blessed with mesmerising views over the Chianti vineyards and enchanting hamlets. Quiet location but not isolated. Local assistant 24 H in case of need - english speaking  …see more

25 Photos

Farmhouse | 7 Bedrooms | sleeps 18

3 Nights min stay

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from £346 /night

£2420 - £3468 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
we are in the middle of the crete senesi's heart , strategy point for found the fantastic and beautiful small medioval village  …see more

19 Photos

Farmhouse | 6 Bedrooms | sleeps 12

2 Nights min stay

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from £93 /night

£646 - £2097 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Beautiful Tuscan country house and cottage set on a natural terrace with commanding views of the Tuscan hills. Deep in the countryside with easy day trips to Florence, Sienna and Perugia.  …see more

21 Photos

Villa | 8 Bedrooms | sleeps 12

Short stays welcome

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from £369 /night

£2581 - £4791 / week

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Key info:

  • Nearest beach 45 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
The Piaggione of Serravalle is like a gateway entrance that protects an uncontaminated hill that seems lost in time and where nature apparently undisturbed articulates its own natural rhythms. Located on one of the highest summits of Chianti, in between Siena and Floren  …see more

20 Photos

Villa | 7 Bedrooms | sleeps 14

5 Nights min stay

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from £165 /night

£1154 - £2500 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Alonestanding villa with private pool in Southern Tuscany. Quiet location and privacy.  …see more

22 Photos

Tower | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £104 /night

£726 - £1936 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Stunning medieval tower near San Gimignano for holiday rentals  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 6

1 night min stay

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from £185 /night

£1291 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Wonderful place to relax, make sports ( walking,archery and swimming) sip our good wine and enjoy our cousine. Our swimming pool is 15x5mt wide and is cleaned using salt and not chlorine.  …see more

21 Photos

Apartment | 2 Bedrooms | sleeps 6

1 night min stay

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from £70 /night

£484 - £1355 / week

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Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Charming holiday apartment in heart of Tuscany; excellent for families and couples seeking relaxation. Just few minutes to Siena, San Gimignano and Florence. Pool and fresco dining area.  …see more

8 Photos

Farmhouse | 2 Bedrooms | sleeps 6

2 Nights min stay

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from £58 /night

£404 - £484 / week

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Key info:

  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
Excursions in the nature, the taste, the cities of art and the well-being. The Lands of the province of Siena offer one series of distances between art, nature, well-being and gastronomy like perhaps no other place to the world: leaving from Siena, with its ducky beau WiFi is available in all areas and is free of charge. Free private parking is possible on site (reservation  …see more

17 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £47 /night

£323 - £565 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
The natural extension of the existing village of Gaiole in Chianti. The 'village-inside-the village' concept that is unique of its kind. The village concept that becomes an integral part of Gaiole in Chianti. l  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 9

7 Nights min stay

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from £116 /night

£807 - £2581 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Thanks to its centrality and good road connection (the Florence-Siena dual carriage-way runs at just 7 km from the property) this place is an excellent starting point for daily trips to the main cultural sites of Tuscany: Colle di Val D'Elsa town is approx. 5 km. far. Within walking distance (approx.500 metres) a small village is offering a market, two bars and a restaurant.  …see more

10 Photos

Apartment | 5 Bedrooms | sleeps 9

Short stays welcome

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from £87 /night

£605 - £1049 / week

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Key info:

  • Nearest beach 95 km
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
A simple old house, functional and warm with manifold opportunities to fully enjoy the Tuscan atmosphere. The terrace with garden in the West side and the olive tree grove on the East, allow you to choose separate locations for your relax. Free in/outside wifi.  …see more

8 Photos

Studio | sleeps 2

3 Nights min stay

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from £57 /night

£396 - £480 / week

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Key info:

  • Nearest beach 40 km
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
'In Cicornia' is a beautiful totally restored 45 square metre studio apartment in the centre of delightful medieval village of Radicondoli. Is the ideal place where you can have a week of deep relax in a small Tuscan village. Is an incredible romantic place The apartment faces onto the main square of the village & therefore is really at the heart of this small com  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 8

3 Nights min stay

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from £89 /night

£621 - £644 / week

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Key info:

  • Nearest beach 90 km
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Large, elegant, comfortable apartment in incomparable surroundings. Peaceful and relaxing with spectacular scenery. 3 km from Castellina in Chianti with its medieval town centre, shops, bars, restaurants. 22 km from Siena., 37km from Florence. No neighbours or noise. Perfect to come home to after the day's excursions. A glass of wine in the garden, dinner under the stars.  …see more

13 Photos

Villa | 3 Bedrooms | sleeps 6

Short stays welcome

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from £115 /night

£803 - £1170 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • 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

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Villa | 5 Bedrooms | sleeps 12

1 night min stay

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from £218 /night

£1525 - £1948 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Farmhouse Casa Orcia is situated in the province of Siena in the peaceful heart of Val d'Orcia, a beautiful landscape of UNESCO patrimony. Security deposit € 500 city tax € 2,50 for person/night up to 4 nights heat on consumption €50/day ask rega  …see more

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Villa | 6 Bedrooms | sleeps 12

Short stays welcome

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from £70 /night

£486 - £1807 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Impressive villa with private pool fantastically located in the heart of Tuscany. 6 bedrooms, huge indoor and outdoor spaces, air-conditioning, high quality traditional finishing, walking distance to shops. Unbeatable value for money.  …see more

15 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £47 /night

£323 - £593 / week

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Key info:

  • Nearest beach 75 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
Our farm is the only one with a horse on the property, offers a beautiful view, surrounded by green gardens, with a wood-burning oven in the central courtyard and have WI-FI internet access. We offer many services and activities of a different kind, for everyone.  …see more

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