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573 Holiday homes in Siena Province

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573 Results  |  
24 Photos

Villa | 9 Bedrooms | sleeps 18

7 Nights min stay

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from £1009 /night

£7057 - £12380 / week

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Key info:

  • Nearest beach 85 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Set on a large estate with extensive views over the Crete Senesi and Siena countryside, this villa is just perfect for family reunions or large group of friends. Built in stone and brick, this Tuscany villa consists of a main villa and a dependence.  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £392 /night

£2742 - £4759 / week

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Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Villa La Torre is a medieval lookout tower, built more than 8 centuries ago on Etruscan foundations, and at a later date incorporated into the farmhouse structure.  …see more

21 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £80 /night

£557 - £847 / week

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Key info:

  • Nearest beach 95 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
This Tuscan 17th century farmhouse with 2 bedrooms, Villa Arpicella, is located very close to Pienza and it enjoys the stunning countryside setting with spectacular wide open views.  …see more

Featured properties

24 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £138 /night

£960 - £2057 / week

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Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
It is the most photographed house in the area, a symbol of the Tuscany countryside, featured on many postcards and calendars simply because it has maintained the charm of the old farmhouse and the surrounding fields, without any new buildings as far as the eye can see.  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 7

3 Nights min stay

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from £202 /night

£1412 - £1775 / week

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Key info:

  • Nearest beach 130 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Farnetella is an old farmhouse dating back to the XVII century, which has been carefully restored respecting all the traditional architectural characteristics, preserving the stone walls, the original wooden beamed ceilings and the terracotta floors.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £346 /night

£2420 - £3186 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Villa Nuti is an elegant XVII century manor only 3 km from the center of Siena. From its unique terrace it enjoys privileged magnificent views of the town with its famous bell towers.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 8

3 Nights min stay

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from £461 /night

£3226 - £5242 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
This comfortable, cosy villa nestles on a sheltered incline among gently rolling hills. These are covered in Brunello wine-producing vineyards, which border the lower pool-terrace. The San Giuseppe winery, from which the house takes its name, is situated nearby.  …see more

21 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £139 /night

£968 - £1936 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Immersed in the green countryside on the outskirts of Siena, Villa Palio offers all the quiet of its natural setting just a stone throw from the very center of the town of Siena.  …see more

18 Photos

Farmhouse | 3 Bedrooms | sleeps 6

Min stay varies

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Key info:

  • Great for children of all ages
  • Pets welcome
  • Private garden
Ancient farmhouse in Tuscany, just 1,5km from the center of Montepulciano with a wonderful view on Valdichiana.Up to 6 people rented all the year. 25 hectars of property with wineyard, olives, trees and truffles. 3 bedrooms, 1 big saloon with central fireplace, big kitc  …see more

24 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £174 /night

£1217 - £1478 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
The old style restoerd flats can offer a perfect feeling of Tuscany. The large garen with view will grant you of unforgettable sunsets over the hills. A large garden with 6x12 mt swimming pool and a very nice barbeque area are at the guest's disposal. In summertime is absolutely nice to go by bike/walking/jogging, it's very easy to find people doing the same  …see more

17 Photos

B&B | 1 Bedroom | sleeps 4

Min stay varies

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Key info:

  • Great for children of all ages
  • Pets welcome
  • Private garden
B&B Tuscany, B&B Siena, B&B Chiusi, rooms in chiusi, sleep in chiusi, etruscan area, rural holidays, cultural holidays, Tuscan countryside, horse riding holidays, cycling holidays.  …see more

24 Photos

Farmhouse | 7 Bedrooms | sleeps 18

3 Nights min stay

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from £92 /night

£642 - £1026 / 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

11 Photos

Apartment | 2 Bedrooms | sleeps 6

4 Nights min stay

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from £55 /night

£385 - £428 / week

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Key info:

  • Nearest beach 60 km
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Quiet apartment, overlooking the valley of Elsa, renovated in 2012, near San Gimignano and Volterra  …see more

24 Photos

Lodge | 3 Bedrooms | sleeps 8

7 Nights min stay

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from £198 /night

£1385 - £2522 / 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
Modern and tastefully decorated cottages with an infinity swimming pool where you can totally relaxed surrounded by the typical tuscany landscape: a fantastic view. Perfect for families, couples or groups of friends to enjoy cultural, art, good wine and italian food.  …see more

21 Photos

Villa | 8 Bedrooms | sleeps 12

Short stays welcome

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from £391 /night

£2736 - £5078 / 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

Apartment | 3 Bedrooms | sleeps 9

Excellent 5/5 

1 night min stay

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from £167 /night

£1167 - £1437 / 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
Enjoy the view, meanwhile swimming in the pool, dine in the outside garden watching the beautiful sunset vew,in front of the chimney during the winter in the comfort of the heated pavements.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

Very Good 4.5/5 

3 Nights min stay

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from £355 /night

£2480 - £2650 / 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
villa with 3 apartment Everyapartment has bedrooms,bathroom and livingroom with kitchen corner big saloon smimmingpool,big garden Caio Alto offers to guests a nice and lovely holiday Asking to Paola and Alessandro (owers ) the guests may have collaboration and help the guests may sell organic products of Factory:oil extravergine DOP Terre diSiena, ,organic Wine  …see more

10 Photos

Villa | 4 Bedrooms | sleeps 4

Excellent 5/5 

Short stays welcome

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from £74 /night

£513 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
Si godono scorci pittoreschi degli Edifici Storici e gli ampi spazi del panorama Toscano . Per gli amanti di MountainBikes , del Relax nei Laghi ,del Wellness alle Terme, ,della cucina Toscana e della arguta simpatia e della cordialita' dei Toscani. Vicinissima a Ristorants,Bar,Farmacia,Banche, Musei Concerti ? Se siete fortunati anche Concerti !!!!!  …see more

12 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £254 /night

£1775 - £2097 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Luxury Tuscan farmhouse and private pool, with stunning views over Montepulciano 4 double bedrooms all with en-suite marble bathrooms  …see more

23 Photos

Villa | 7 Bedrooms | sleeps 23

7 Nights min stay

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from £550 /night

£3847 - £5984 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Casale, montepulciano, villa, piscina, vigneti, matrimonio in toscana, matrimonio in Italia, Italy, Tuscany Antico casale, completamente restaurato e suddiviso in 7 accoglienti appartamenti  …see more

12 Photos

Villa | 8 Bedrooms | sleeps 25

7 Nights min stay

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from £98 /night

£684 - £2992 / 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

24 Photos

Apartment | 2 Bedrooms | sleeps 8

3 Nights min stay

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from £88 /night

£611 - £671 / 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

18 Photos

Villa | 3 Bedrooms | sleeps 6

Short stays welcome

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from £146 /night

£1018 - £1873 / week

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Key info:

  • Nearest beach 50 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 | 3 Bedrooms | sleeps 6

Short stays welcome

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from £123 /night

£855 - £1616 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • 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

24 Photos

Villa | 3 Bedrooms | sleeps 7

3 Nights min stay

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from £178 /night

£1240 - £1582 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
The villa is the ideal starting point to visit the Val di Chiana and Val d'Orcia with its wonderful medieval towns such as Cortona, Montepulciano, San Quirico d'Orcia, Pienza, as well as Montalcino and San Gimignano and the beautiful art cities of Siena and Florence.  …see more

24 Photos

Villa | 9 Bedrooms | sleeps 18

Excellent 5/5 

3 Nights min stay

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from £245 /night

£1710 - £3975 / week

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Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Beautiful Tuscan detached villa with swimming pool near Siena to rent for sleeps up to-10-16-20-It is an ideal place for families to spend a relaxing holiday far from town noises among the peace of the country. A heaven of peace in the heart of Montagnola Senese at a stone's throw from Siena.  …see more

20 Photos

Farmhouse | 3 Bedrooms | sleeps 8

Short stays welcome

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from £80 /night

£556 - £727 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Summer holiday rental, self-catering, romantic view, villa in Tuscany, city of art, Siena, Florence, San Gimignano, Volterra, Monteriggioni, Certaldo,Radicondoli, Belforte,San Galgano, Massa Marittima, Populonia.  …see more

20 Photos

Farmhouse | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £49 /night

£342 - £599 / 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
Summer holiday rental, self-catering, romantic view, villa in Tuscany, city of art, Siena, Florence, Pisa, San Gimignano, Volterra, Monteriggioni, Certaldo,Radicondoli, Belforte,San Galgano, Massa Marittima, Populonia, Montepulciano, Montalcino, Pienza, Cortona.  …see more

18 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £281 /night

£1967 - £3249 / 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

11 Photos

Farmhouse | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £64 /night

£445 - £1240 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Farmhouse with Garden and Pool Fantastic Location near the most important Turistic Points Sleeps 6 (3 Bedrooms)  …see more

15 Photos

Cottage | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £68 /night

£471 - £1180 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Cottage With Private Garden And Hills View Panoramic Location,10 Min Walk From The Lovely Medieval Village Of Casole D'elsa Sleeps 4 (2 Bedrooms) wi fi SYSTEM  …see more

15 Photos

Farmhouse | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £55 /night

£385 - £761 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Elegnt Accommodation With Pool And 360° Hills Views Ideal For Families And Couples, In The Heart Of The Splendid Chianti Countryside. Sleeps 4 + 1 (2 Bedrooms)  …see more

16 Photos

Cottage | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £55 /night

£385 - £984 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Sleeps 4. (2 bedrooms) 'Leccio' is a comfortable farmhouse cottage with splendid pool. Authentically restored to reveal original chestnut beams, terracotta tile ceilings and floors. Located in the heart of the country side but less than 15 minute walk to village.  …see more

19 Photos

Farmhouse | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £62 /night

£428 - £761 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
  • Private garden
Sleeps 4. 2 bedrooms 90 m².The Ciliegio House is composed by a typical Tuscan living room, kitchen, two double bedrooms and a bathroom with shower. Outdoor: swimming pool exclusive view on the tuscan hills , Barbecue area, Private lighting system, Parking.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 12

Excellent 5/5 

3 Nights min stay

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from £185 /night

£1291 - £2380 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Self-catering Tuscan villa with private pool ideal for 8-12 persons. Each room with ensuite bathroom Private infinity swimming pool The skilful renovation of the premises has fully preserved the typical rustic Tuscan style.  …see more

24 Photos

B&B | 1 Bedroom | sleeps 2

1 night min stay

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from £74 /night

£513 - £590 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
Very spacious and elegant rooms in a b&b with restaurant. Air conditioning, wi-fi, private bathroom with shower, swimming pool. Breakfast is included. The enviroment is a historic country estate, it is a great location for visiting the most beautiful places in Tuscany. Guests have access to the entire estate, which is also an educational farm very interesting for the kids.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

4 Nights min stay

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from £70 /night

£490 - £690 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
A spacious 1 bed apartment with garden and bbq terrace, in a picturesque setting, only a short walk to local services. Enjoy free use of cycles & gym or just relax by the pool. Launderette & internet services add home comforts and a glass of wine greets you on arrival. Minore is ideally situated to enjoy the areas premier events including Siena Palio & Gaiole Eroica.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 9

Excellent 5/5 

3 Nights min stay

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from £156 /night

£1089 - £2178 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Self-catering Tuscan villa with private pool ideal for 8-9 persons. Each room with ensuite bathroom Very close to the town  …see more

24 Photos

House | 1 Bedroom | sleeps 5

Very Good 4.5/5 

3 Nights min stay

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from £49 /night

£339 - £428 / week

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Key info:

  • Nearest beach 50 km
  • Swimming pool
  • Great 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

24 Photos

Farmhouse | 5 Bedrooms | sleeps 12

2 Nights min stay

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from £194 /night

£1355 - £1948 / week

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Key info:

  • Not suitable for children
  • Car advised
  • No pets allowed
Farmhouse Casa Orcia - holiday accommodation in Tuscany with swimming pool is for discerning travelers wishing to spend their holidays in Tuscany. This rental farmhouse is wonderful for a family holiday and located between Pienza (where the english patient was filmed) a  …see more

18 Photos

Apartment | 2 Bedrooms | sleeps 4

Very Good 4.5/5 

5 Nights min stay

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from £72 /night

£500 - £850 / week

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Key info:

  • Nearest beach 66 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
Holiday apartment with shared pool. Its rural position offers complete relaxation and a wonderful panoramic view. Near Volterra and San Gimignano, it's a perfect base to visit Florence, Pisa and Siena. Perfect for families and couples. The area boasts some of the best views Tuscany has the offer, the entire area being a national park.  …see more

24 Photos

Farmhouse | 2 Bedrooms | sleeps 8

3 Nights min stay

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from £43 /night

£300 - £513 / week

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Key info:

  • Nearest beach 80 km
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
The apartment is an excellent starting point for excursions on foot or mountain bike in the via Francigena or Montagnola senese.Siena is about 13 km, Monteriggioni approx. 8 km. you can do excursions also to s. Gimignano, Colle di Val D'elsa, Casole, s. Galgano  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £162 /night

£1130 - £2138 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Detached villa with private pool in southern Tuscany. 4 bedrooms up to 10 sleeps.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 12

6 Nights min stay

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from £180 /night

£1259 - £2259 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Luxurious detached villa in hilly and quiet location with a beautiful panorama in southern Tuscany. Pool, Jacuzzi (all for private use of the tenant).  …see more

21 Photos

Villa | 9 Bedrooms | sleeps 21

7 Nights min stay

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from £404 /night

£2823 - £3952 / 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
Detached villa with private pool 35 km eastern of Siena. It is an expansive property providing a high standard of accommodation. Tasteful furnished. Hilly and quiet location. The whole property is for private use of the tenant. 9 bedrooms, 17+4 sleeps. Billiard room.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £196 /night

£1367 - £2271 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
This comfortably furnished country style Tuscan villa sleeps up to ten persons. Set amongst a mature well tended garden with its own private swimming pool. The property is in a great location only five minutes away from Gaiole.  …see more

18 Photos

Farmhouse | 8 Bedrooms | sleeps 22

3 Nights min stay

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from £254 /night

£1775 - £2425 / week

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Key info:

  • Nearest beach 45 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Perfect location self - catering accommodation for a group holiday in the historical and cultural heart of Tuscany. Conveniently situated in a small village with restaurants, mini market and cafe/bar all at our door step. Beautiful setting for a memorable occasion.  …see more

24 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £74 /night

£513 - £1496 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Pets welcome
www.ilcellese.it  …see more

13 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £74 /night

£513 - £1026 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
CHIANTI , TOSCANA , AGRITURISMO , WINE , COOKING CLASS , LANDSCAPE , VIEW , SWIMMING POOL  …see more

23 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £52 /night

£363 - £444 / week

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Key info:

  • Nearest beach 55 km
  • Great for children of all ages
  • Car advised
  • Pets welcome
Excellent base for exploring the jewels of Tuscany.  …see more