List your home
Apply filters
£ to

1,564 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 locations
  • Abbadia San Salvatore (3)
  • Asciano (66)
  • Badia A Elmi (4)
  • Bagno Vignoni (12)
  • Brolio (9)
  • Buonconvento (24)
  • Casetta (8)
  • Casole d'Elsa (77)
  • Castellina in Chianti (72)
  • Castelnuovo Berardenga (67)
  • Castiglione d'Orcia (10)
  • Cetona (43)
  • Chianciano Terme (16)
  • Chiusdino (3)
  • Chiusi (20)
  • Colle di Val d'Elsa (52)
  • Gaiole in Chianti (95)
  • Gracciano di Colle Val d'Elsa (4)
  • Guazzino (14)
  • Iesa (12)
  • Isola d'Arbia (1)
  • Montalcino (52)
  • Montepulciano (90)
  • Monteriggioni (34)
  • Monteroni d'Arbia (42)
  • Monticiano (41)
  • Murlo (5)
  • Piancastagnaio (1)
  • Pienza (36)
  • Poggibonsi (76)
  • Radda (20)
  • Radicofani (20)
  • Radicondoli (37)
  • San Casciano dei Bagni (30)
  • San Gimignano (224)
  • San Giovanni d'Asso (24)
  • San Quirico D'Orcia (8)
  • Sarteano (28)
  • Siena (88)
  • Sinalunga (37)
  • Sovicille (17)
  • Torrita di Siena (11)
  • Trequanda (7)
  • Ulignano (24)

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
2,512 properties
Florence
982 properties
Venice, Veneto
501 properties
Trapani
484 properties
Lucca
468 properties
Amalfi Coast
452 properties
Cortona
423 properties
Palermo
413 properties
Sorrento, Campania
353 properties
Cefalu
316 properties
San Gimignano
289 properties
Taormina
276 properties
Greve in Chianti
263 properties
Massa Lubrense
246 properties

Filters applied: Restricted mobility (1,564)

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
1,564 Results  |  
20 Photos

House | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £287 /night

£2009 - £3210 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
Once a watermill. Original architecture and contemporary design. Close to San Gimignano.  …see more

20 Photos

House | 6 Bedrooms | sleeps 16

7 Nights min stay

Add to shortlist

from £537 /night

£3759 - £6283 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Elegant country décor. Airy and spacious rooms. Air conditioning in the first floor bedrooms. Optional guest house.  …see more

20 Photos

Farmhouse | 6 Bedrooms | sleeps 11

7 Nights min stay

Add to shortlist

from £345 /night

£2412 - £4831 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Located in the Volpaia hamlet (Chianti region) with local restaurant. Renowned local wine produced on estate. Private and panoramic position. Tennis court on the estate.  …see more

Featured properties

18 Photos

Farmhouse | 5 Bedrooms | sleeps 9

7 Nights min stay

Add to shortlist

from £479 /night

£3347 - £5242 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
In the heart of Chianti Classico. Very close to the village of Radda. Furnished in refined country style.  …see more

17 Photos

Farmhouse | 7 Bedrooms | sleeps 18

7 Nights min stay

Add to shortlist

from £537 /night

£3759 - £6444 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Modern design combined to the original structure. Modern facilities including air conditioning. Very peaceful and secluded position in the Chianti region. Optional guest house.  …see more

14 Photos

Chateau | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £345 /night

£2412 - £3468 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Very stylish and comfortable. Located in beautiful hamlet in Chianti. Very panoramic furnished terrace.  …see more

16 Photos

Farmhouse | 7 Bedrooms | sleeps 13

7 Nights min stay

Add to shortlist

from £689 /night

£4823 - £7194 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Breathtaking views over the Chianti Classico valleys. Attractive and panoramic terrace.  …see more

10 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £60 /night

£414 - £636 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
Villa / Farmhouse / Home in Volterra with 1 bedrooms sleeps 2  …see more

10 Photos

Farmhouse | 2 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £64 /night

£444 - £464 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Colle Di Val D'elsa with 2 bedrooms sleeps 4  …see more

5 Photos

Apartment | 1 Bedroom | sleeps 2

4 Nights min stay

Add to shortlist

from £85 /night

£595 / week

View

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

10 Photos

Townhouse | 2 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £112 /night

£783 - £1199 / week

View

Key info:

  • Not suitable for children
  • Pets welcome

"Vanessa", 3-room semi-detached house 110 m2 on 2 levels, on the ground floor: large living room with 2 sleeping possibilities, open fireplace and satellite-TV. Kitchen (oven, dishwasher, freezer). Shower/bidet/WC. Upper floor: 1 double bedroom. 1 room with 2 beds. Shower/bidet  …see more

10 Photos

Townhouse | 2 Bedrooms | sleeps 4

1 night min stay

Add to shortlist

from £86 /night

£600 - £991 / week

View

Key info:

  • Not suitable for children
  • Pets welcome

"Capanna di Sopra", 3-room semi-detached house 90 m2 on 2 levels, on the ground floor, renovated, nice and tasteful furnishings: living/dining room with open fireplace, dining table and satellite-TV. Exit to the garden, to the terrace. 1 double bedroom. Exit to the terrace.  …see more

24 Photos

House | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £287 /night

£2009 - £2299 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
About our villas in italy This lovely property is located only 5 Kms from the centre of San Gimignano, famous for its beautiful towers. This is the place for those who look for piece and quiet, who like nature, gardens, birds.  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

4 Nights min stay

Add to shortlist

from £90 /night

£627 - £1052 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 3 bedrooms sleeps 6  …see more

8 Photos

Villa | 5 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £196 /night

£1368 - £2138 / week

View

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

12 Photos

Farmhouse | 4 Bedrooms | sleeps 7

2 Nights min stay

Add to shortlist

from £225 /night

£1573 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
Villa / Farmhouse / Home in Gaiole In Chianti with 4 bedrooms sleeps 7  …see more

24 Photos

Farmhouse | 6 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £345 /night

£2412 - £4000 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
This exquisitely restored farmhouse is situated in one of the most beautiful positions, right in the heart of Chianti Classico. From its secluded position the views are absolutely stunning, with all the windows framing a picture of the lovely Chianti countryside  …see more

11 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £87 /night

£605 - £932 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
Villa / Farmhouse / Home in Volterra with 2 bedrooms sleeps 4  …see more

22 Photos

House | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £277 /night

£1936 - £2339 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
La Commenda is located in a quiet and secluded position in the Volpaia hamlet. This small, rural hamlet with its fortified walls dating from Medieval times, is one of the best remaining examples of its kind in Tuscany. It is located, just north of Radda in Chianti  …see more

19 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £85 /night

£589 - £759 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 1 bedrooms sleeps 2  …see more

24 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £43 /night

£299 - £593 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
Country Resort in Colle Di Val D'elsa with 1 bedrooms sleeps 2  …see more

6 Photos

Farmhouse | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £172 /night

£1202 - £2998 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
Beautiful stone-built farmhouse that has been perfectly restored and equipped with all of the modern conveniences, situated in the heart of the Chianti Classico close to the typical tuscan town of Radda.  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 3

3 Nights min stay

Add to shortlist

from £54 /night

£377 - £471 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Siena apartment with easy access to the town centre  …see more

24 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £43 /night

£299 - £593 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
Country Resort in Colle Di Val D'elsa with 1 bedrooms sleeps 2  …see more

21 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

Add to shortlist

from £38 /night

£265 - £360 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

24 Photos

Farmhouse | 1 Bedroom | sleeps 4

3 Nights min stay

Add to shortlist

from £43 /night

£299 - £593 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
Country Resort in Colle Di Val D'elsa with 1 bedrooms sleeps 4  …see more

22 Photos

Apartment | 1 Bedroom | sleeps 5

7 Nights min stay

Add to shortlist

from £44 /night

£308 - £398 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

24 Photos

Farmhouse | 2 Bedrooms | sleeps 5

3 Nights min stay

Add to shortlist

from £63 /night

£439 - £726 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
Country Resort in Colle Di Val D'elsa with 2 bedrooms sleeps 5  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 3

3 Nights min stay

Add to shortlist

from £31 /night

£214 - £308 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • No pets allowed
nice and comfortable apartments in walking distance from the village .  …see more

24 Photos

Farmhouse | 2 Bedrooms | sleeps 5

3 Nights min stay

Add to shortlist

from £63 /night

£439 - £726 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
Country Resort in Colle Di Val D'elsa with 2 bedrooms sleeps 5  …see more

24 Photos

Farmhouse | 4 Bedrooms | sleeps 10

3 Nights min stay

Add to shortlist

from £100 /night

£696 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
Country Resort in Colle Di Val D'elsa with 4 bedrooms sleeps 10  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

4 Nights min stay

Add to shortlist

from £54 /night

£377 - £471 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
holiday apartments in Montepulciano. Farm stay in a wine estate in Montepulciano  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £220 /night

£1539 - £2821 / week

View

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

20 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

Add to shortlist

from £40 /night

£274 - £360 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

22 Photos

Apartment | 2 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £46 /night

£317 - £454 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

24 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £63 /night

£439 - £726 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
Country Resort in Colle Di Val D'elsa with 2 bedrooms sleeps 4  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £655 /night

£4581 - £7601 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
Villa in San Casciano Dei Bagni with 5 bedrooms sleeps 10  …see more

23 Photos

Apartment | 2 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £47 /night

£328 - £424 / week

View

Key info:

  • Not suitable for children
  • Some pets are welcome - please contact the owner
Holiday Apartment in Radicofani with 2 bedrooms sleeps 6  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 18

7 Nights min stay

Add to shortlist

from £208 /night

£1454 - £3420 / week

View

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

14 Photos

Apartment | 1 Bedroom | sleeps 3

3 Nights min stay

Add to shortlist

from £31 /night

£214 - £308 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • No pets allowed
nice and comfortable apartments in walking distance from the village  …see more

12 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £180 /night

£1259 - £1835 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Characteristic Tuscan country home in panoramic position, near the small town of Rigomagno between Cortona and Siena.  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £88 /night

£613 - £799 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in San Gimignano with 2 bedrooms sleeps 4  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

Short stays welcome

Add to shortlist

from £70 /night

£486 - £1807 / week

View

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

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £52 /night

£363 - £420 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
Villa / Farmhouse / Home in Cetona with 2 bedrooms sleeps 4  …see more

20 Photos

Farmhouse | 1 Bedroom | sleeps 2

5 Nights min stay

Add to shortlist

from £51 /night

£355 - £371 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Colle Di Val D'elsa with 1 bedrooms sleeps 2  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 5

3 Nights min stay

Add to shortlist

from £117 /night

£813 - £1124 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Carming apartments in a medieval hamlet in heart of Tuscany, all the apartments have been carefully restored, swimming pool  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 3

3 Nights min stay

Add to shortlist

from £53 /night

£371 - £638 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
The different apartments host from 2 to 6 guests and are provided with a living room, kitchenette, 1 to 3 double or twin bedrooms and 1 to 3 bathrooms with shower and/or bathtub.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £49 /night

£339 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
This exclusive loft with breath taking views is the ideal reantal for a couple. The apartment Located in south of Tuscany is in a very good position to explore, Siena Area.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £89 /night

£621 - £881 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Carming apartments in a medieval hamlet in heart of Tuscany, all the apartments have been carefully restored, swimming pool  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £81 /night

£565 / week

View

Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Villa Vignacce is a villa in Tuscany divided into three apartments, all recently remodelled, that can be joined to become a single villa with private pool.  …see more