List your home
Apply filters
£ to

1,416 Holiday homes in Siena Province

Reset search

Show results on map

Filter your search

Price per day

£ to

Bedrooms

Location

  • Italy Clear
  • Tuscany Clear
  • Siena Province Clear
  • All towns
  • Abbadia San Salvatore (5)
  • Asciano (51)
  • Badia A Elmi (4)
  • Bagno Vignoni (2)
  • Brolio (10)
  • Buonconvento (25)
  • Casetta (11)
  • Casole d'Elsa (70)
  • Castellina in Chianti (67)
  • Castelnuovo Berardenga (48)
  • Castiglione d'Orcia (8)
  • Cetona (42)
  • Chianciano Terme (14)
  • Chiantishire (1)
  • Chiusdino (7)
  • Chiusi (17)
  • Colle di Val d'Elsa (41)
  • Gaiole in Chianti (59)
  • Gracciano di Colle Val d'Elsa (7)
  • Guazzino (10)
  • Iesa (2)
  • Montalcino (49)
  • Montepulciano (80)
  • Monteriggioni (24)
  • Monteroni d'Arbia (48)
  • Monticiano (29)
  • Murlo (9)
  • Piancastagnaio (5)
  • Pienza (58)
  • Poggibonsi (63)
  • Radda (25)
  • Radicofani (18)
  • Radicondoli (56)
  • San Casciano dei Bagni (21)
  • San Gimignano (196)
  • San Giovanni d'Asso (35)
  • San Quirico D'Orcia (7)
  • Sarteano (27)
  • Siena (65)
  • Sinalunga (37)
  • Sovicille (19)
  • Torrita di Siena (19)
  • Trequanda (8)
  • Ulignano (17)

more +

less -

Also consider

Coastal Cottages
222 properties
Sardinia
478 properties
Tuscany
3,181 properties
Lake Garda Area
103 properties
Lake Como Area
494 properties
Sicily
634 properties
Rome
2,530 properties
Florence
985 properties
Trapani
505 properties
Venice, Veneto
498 properties
Amalfi Coast
465 properties
Lucca
439 properties
Palermo
423 properties
Cortona
409 properties
Sorrento, Campania
350 properties
Cefalu
311 properties
San Gimignano
299 properties
Taormina
275 properties
Alghero
260 properties
Syracuse
259 properties

Filters applied: BBQ (1,416)

To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more
1,416 Results  |  
23 Photos

Apartment | 2 Bedrooms | sleeps 4

Very Good 4.5/5 

5 Nights min stay

Add to shortlist

from £83 /night

£575 - £850 / week

View

Key info:

  • Nearest beach 45 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Holiday apartment with shared pool and gardens. Its rural position offers complete relaxation and a wonderful panoramic view. Near Volterra and San Gimignano, it's a perfect starting point for visiting Florence, Pisa and Siena. Perfect for families or couples. Excellent restaurants, sport facilities, city tours, and excursions in beautiful Tuscan countryside.  …see more

12 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £58 /night

£400 - £544 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
Il Baroncino stands alone among the rolling hills, in 8 hectares of private land, with many age-old chestnut and oak trees.  …see more

21 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

Add to shortlist

from £72 /night

£504 - £640 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
This property impresses at first sight with its superb location and its wonderful garden.  …see more

Featured properties

10 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £74 /night

£512 - £608 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
Casale Oliveta is located in a little hamlet with a few houses up in the hills.  …see more

12 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £388 /night

£2712 - £3992 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Podere Montepulciano sits on a hill just ten minutes drive away from captivating Renaissance town Pienza.  …see more

13 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £88 /night

£616 - £1000 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
Il Baroncino stands alone among the rolling hills, in 8 hectares of private land, with many age-old chestnut and oak trees  …see more

12 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £74 /night

£512 - £608 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
Casale Oliveta is located in a little hamlet with a few houses up in the hills.  …see more

14 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £92 /night

£640 - £768 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
  • Private garden
Casale Oliveta is located in a little hamlet with a few houses up in the hills  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £92 /night

£640 - £768 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
  • Private garden
Casale Oliveta is located in a little hamlet with a few houses up in the hills.  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £85 /night

£592 - £928 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
Il Baroncino stands alone among the rolling hills, in 8 hectares of private land, with many age-old chestnut and oak trees.  …see more

13 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £628 /night

£4392 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
  • Private garden
La Giocosa is located in the most desirable region south of Siena, in the Val d'Orcia, an enchanting and miraculously unspoilt valley in southern Tuscany, listed as UNESCO world heritage in 2004.  …see more

20 Photos

Manor House | 8 Bedrooms | sleeps 20

7 Nights min stay

Add to shortlist

from £258 /night

£1800 - £3040 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • No pets allowed
  • Private garden
Beautiful farmhouse divided into separate apartments. Large swimming pool and children's playground.  …see more

15 Photos

Farmhouse | 8 Bedrooms | sleeps 20

7 Nights min stay

Add to shortlist

from £286 /night

£2000 - £2840 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
The stone farmhouse, probably an old fortified farm, has been completely restored in recent months, using original architectural features and materials. The swimming pool has a waterfall feature and is in a panoramic position.  …see more

7 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £85 /night

£595 - £854 / week

View

Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
Farmhouse Graziano Stalla is one of 3 independent country homes located on a vast farm estate, where stately cypress trees welcome you to a captivating Tuscan experience.andnbsp;The house is at the medieval town of San Gimignano with its well-known towers, as well as a  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £102 /night

£711 - £1080 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
The apartment Marta is located in Cortona in Arezzo in Tuscany and is really perfect for a relaxed Tuscan holiday. The apartment is set on the first floor of the main house, Apartment Rosangela. The house has been decorated in true Tuscan style which make the entire pla  …see more

24 Photos

Farmhouse | 5 Bedrooms | sleeps 12

2 Nights min stay

Add to shortlist

from £192 /night

£1344 - £1932 / week

View

Key info:

  • Not suitable for children
  • 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

15 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £102 /night

£713 - £1005 / week

View

Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
Situated on a farm estate in the lovely Tuscan commune of Casole d'Elsa in Siena and enclosed by abundant cypress trees and oak wood, the Farmhouse Graziano Pollaio was once the old poultry pen of the ancient farm estate and has now been renovated to offer guests a char  …see more

24 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £79 /night

£548 - £754 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Apartment Grazie An apartment that has been passed through four different generations and carries all the tradition and culture of the times with it, Apartment Grazia isandnbsp;one of the three apartments in the Apartment Rosangela, this rental house in Italy is histor  …see more

24 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £90 /night

£629 - £917 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
The Cottage Allegra is not just a rental home for you to enjoy your holiday in, it is also a home full of history and culture so strong that you can feel it in the air. This rental house, Cottage Allegra sits in Cortona, Arezzo, Tuscany. One of the main cottages of Apa  …see more

8 Photos

Villa | 9 Bedrooms | sleeps 12

3 Nights min stay

Add to shortlist

from £186 /night

£1300 - £2900 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
Villa Hamby is a beautifully restored five bedroom four bathroom country house with a great deal of warmth and charm. The villa has a great views across the Valdarno valley that stretches from Florence to Rome with the Appenini mountains as a dramatic backdrop to the co  …see more

24 Photos

Villa | 11 Bedrooms | sleeps 22

3 Nights min stay

Add to shortlist

from £826 /night

£5780 - £10240 / week

View

Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
Halfway between Siena and Florence in the splendid Tuscan is the Villa Azzurra. The location of the villa is in a strategic position where it is easy to admire the most important Tuscan cities without having to renounce a relaxing and tranquil holiday in the countryside  …see more

12 Photos

Villa | 5 Bedrooms | sleeps 10

3 Nights min stay

Add to shortlist

from £186 /night

£1300 - £2900 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
Villa Dan is located between the cities of Arezzo, Florence and Siena, at the quaint old town of Figline Valdarno with its ancient piazza and historical buildings. The Villa Dan has 5 bedrooms and 3bathrooms, situated in Figline Valdarno, with a magnicificient view. On  …see more

24 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £61 /night

£423 - £548 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
The best way to describe the Apartment Lia would be to call it, traditional yet modern. The motto of the owners of this quaint apartment is 'We create happinessand that's exactly what you can expect if you choose to spend your vacation here! The apartment has been owned  …see more

12 Photos

Villa | 6 Bedrooms | sleeps 11

3 Nights min stay

Add to shortlist

from £186 /night

£1300 - £2900 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Perched on a green and forested valley of the Chianti, in the small picturesque village of Lucolena, sits Villa Luce, a comfortable country home with a private pool and open views from its raised terraces. The well-tended terraced gardens are planted with flowers typic  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 8

3 Nights min stay

Add to shortlist

from £267 /night

£1866 - £3053 / week

View

Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Casale Reggello is located amidst the gently rolling Tuscan hills, between Pienza and Montepulciano, complitely surrounded by organic plantations.The rooms have been decorated with colours that recall the typical plants of the area : Lavender, Rose hip, Strawberry tree. We can organize for you a typical Tuscan dinner with hand-made pasta,coupled with the excellent local wine.  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 14

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £309 /night

£2160 - £3840 / week

View

Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Pets welcome
  • Private garden
Trip Advisor - Certificate of Excellence award 2014 SPECIAL OFFERS 2014!! Beautiful villa in panoramic position with private pool, Hot Tub. 14persons.Peaceful location, ideal for families or groups seeking relaxation. 7 bedrooms / 5 bathrooms. Only 15km from Siena. Price all included, no extra charges and costs!!!  …see more

20 Photos

Apartment | 3 Bedrooms | sleeps 9

Excellent 5/5 

1 night min stay

Add to shortlist

from £166 /night

£1158 - £1425 / week

View

Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages 5
  • 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

20 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £532 /night

£3720 - £7000 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • No pets allowed
  • Private garden
Incredible views over the Tuscan countryside. Beautiful garden with swimming pool heated by solar panels.  …see more

17 Photos

Farmhouse | 5 Bedrooms | sleeps 12

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £218 /night

£1520 - £2560 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Beautiful farmhouse with swimming pool and children's playground  …see more

19 Photos

Cottage | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £149 /night

£1040 - £1840 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • No pets allowed
  • Private garden
Cottage with swimming pool and small lake.  …see more

20 Photos

Manor House | 7 Bedrooms | sleeps 14

7 Nights min stay

Add to shortlist

from £852 /night

£5960 - £7640 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Tenth century posting house which has kept its charm. Large garden with swimming pool.  …see more

20 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £320 /night

£2240 - £3080 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • No pets allowed
  • Private garden
Farmhouse with swimming pool  …see more

19 Photos

Villa | 5 Bedrooms | sleeps 11

7 Nights min stay

Add to shortlist

from £606 /night

£4240 - £7840 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
Swimming pool (13x4 meters) with heated changing room, garden, 30 hectares of private wood and orchard.  …see more

20 Photos

Villa | 1 Bedroom | sleeps 16

7 Nights min stay

Add to shortlist

from £269 /night

£1880 - £2640 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Pets welcome
  • Private garden
Beautiful country house with swimming pool. Pets allowed. sjfa;sdl fjks;f as;fkl jfk;lj asfklj fklafj klfj ;fklj dfk;lj afklja sfkalsjd faklfj kldfj as;fkl ja;fkl jas  …see more

20 Photos

Farmhouse | 7 Bedrooms | sleeps 14

7 Nights min stay

Add to shortlist

from £686 /night

£4800 - £6880 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Fantastic farmhouse with heated pool. Activities organized and chef, babysitter and driver available.  …see more

20 Photos

Villa | 1 Bedroom | sleeps 20

7 Nights min stay

Add to shortlist

from £166 /night

£1160 - £1880 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • No pets allowed
  • Private garden
Farmhouse divided into 3 apartments with swimming pool and children's playground. sjfa;sdl fjks;f as;fkl jfk;lj asfklj fklafj klfj ;fklj dfk;lj afklja sfkalsjd faklfj kldfj as;fkl ja;fkl jas  …see more

19 Photos

Villa | 1 Bedroom | sleeps 20

7 Nights min stay

Add to shortlist

from £440 /night

£3080 - £4560 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Beautifully renovated farmhouse divided into apartments with swimming pool. sjfa;sdl fjks;f as;fkl jfk;lj asfklj fklafj klfj ;fklj dfk;lj afklja sfkalsjd faklfj kldfj as;fkl ja;fkl jas  …see more

20 Photos

Manor House | 9 Bedrooms | sleeps 18

7 Nights min stay

Add to shortlist

from £1000 /night

£7000 - £13760 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Beautiful stone manor house with heated swimming pool and outdoor heated jacuzzi.  …see more

17 Photos

Farmhouse | 3 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £120 /night

£840 - £1440 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • No pets allowed
  • Private garden
Small farmhouse with swimming pool which can be covered.  …see more

20 Photos

Villa | 1 Bedroom | sleeps 12

7 Nights min stay

Add to shortlist

from £178 /night

£1240 - £1880 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
This was an old monastery during the first half of the sixteenth century and went on to become a summer residence for the friars of Monte Oliveto Maggiore. It enjoys beautiful views across a valley. Old farmhouse, well restored, divided into three apartments.  …see more

20 Photos

Villa | 1 Bedroom | sleeps 10

7 Nights min stay

Add to shortlist

from £252 /night

£1760 - £2880 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Pets welcome
  • Private garden
Beautiful stone built villa with swimming pool. sjfa;sdl fjks;f as;fkl jfk;lj asfklj fklafj klfj ;fklj dfk;lj afklja sfkalsjd faklfj kldfj as;fkl ja;fkl jas  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 5

Excellent 5/5 

1 night min stay

Add to shortlist

from £77 /night

£535 - £653 / week

View

Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
In the middle of the Siena hills facing the Cecina valley, Ulivo is situated within the villa of Il Bel Canto at a short distance from Volterra, San Gimignano, Siena & the sea coast. Ideal for relacing and enjoying the beautiful 360 degrees view.  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £458 /night

£3200 - £4320 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Situated on a farm of 150 hectares producing excellent extra virgin olive oil, the farmhouse is set on a kind of natural terrace overlooking the lovely valley below.  …see more

15 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £126 /night

£880 - £1680 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Pets welcome
Typical Italian agritourism with swimming pool.  …see more

18 Photos

Farmhouse | 6 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £172 /night

£1200 - £2040 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
  • Private garden
Beautiful farmhouse with swimming pool.  …see more

9 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

Add to shortlist

from £49 /night

£340 - £382 / week

View

Key info:

  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
ersonal check in and check out, guests will have my mobile telephone number for any possible further assistance required. I can organize wine tours , tuscan cookery courses , horse riding. A full brochure describing all local activities is provided upon arrival . stunning gardens of La Foce are worth a visit.we recommend the Thermal Spas in Chianciano ,Bagno Vignoni.  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £152 /night

£1060 - £1696 / week

View

Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Pets welcome
  • Private garden
Private viila and swimming pool deeped in nature and quiet.We rent out the whole house,so you could enjoy your holiday without any disturb.  …see more

10 Photos

House | 1 Bedroom | sleeps 3

Short stays welcome

Add to shortlist

from £61 /night

£424 - £446 / week

View

Key info:

  • Great for children of all ages 5
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
Tuscany, self catering, holiday let, Italy, romantic holiday, honey moon, casale  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

Short stays welcome

Add to shortlist

from £146 /night

£1018 - £3392 / week

View

Key info:

  • Suitable for children over
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
The villa stands independent on the top of a hill and it's ideal for those who want to enjoy the peace of the green Tuscany hills all around the house with a beautiful landscape and wide, superb views.  …see more

20 Photos

Farmhouse | 5 Bedrooms | sleeps 10

Very Good 4.5/5 

4 Nights min stay

Add to shortlist

from £286 /night

£2000 - £2750 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Beautiful Tuscan home, lovingly restored for maximum seclusion and relaxation. With masses of character, this is a truly wonderful old large farmhouse, with large grounds and plenty of outside easting, snoozing and relaxing areas The large pool house overlooks the swimming pool and is perfect for long lazy lunches out of the direct sun  …see more