Holiday rentals in Province of Siena: Villas, Cottages and Apartments

Close

View larger map

Price per night

to

Bedrooms

Bathrooms

Location

  • Italy
  • Tuscany
  • Province of Siena
  • All locations
  • Abbadia San Salvatore (4)
  • Asciano (123)
  • Bagni di San Filippo (2)
  • Bagno Vignoni (15)
  • Brenna (5)
  • Buonconvento (79)
  • Campiglia d'Orcia (4)
  • Casciano (3)
  • Casole d'Elsa (179)
  • Castellina In Chianti (145)
  • Castelmuzio (12)
  • Castelnuovo Berardenga (156)
  • Castiglioncello del Trinoro (12)
  • Castiglione D'Orcia (39)
  • Cetona (90)
  • Chianciano Terme (64)
  • Chiusdino (35)
  • Chiusi (46)
  • Colle di Val d'Elsa (181)
  • Gaiole in Chianti (160)
  • Gallina (8)
  • Le Piazze (8)
  • Lucarelli (4)
  • Lucignano d'Arbia (3)
  • Moltacino (2)
  • Monastero d'Ombrone (1)
  • Montalcino (150)
  • Montecchio (10)
  • Montepulciano (278)
  • Monteriggioni (84)
  • Monteroni d'Arbia (39)
  • Monticiano (28)
  • Montisi (22)
  • Murlo (34)
  • Orgia (5)
  • Palazzone (15)
  • Petroio (2)
  • Piancastagnaio (1)
  • Pienza (160)
  • Pievescola (13)
  • Poggibonsi (154)
  • Radda in Chianti (78)
  • Radicofani (68)
  • Radicondoli (78)
  • Rapolano Terme (103)
  • Rocca d'Orcia (3)
  • Rosia (6)
  • San Casciano dei Bagni (78)
  • San Gimignano (413)
  • San Giovanni d'Asso (56)
  • San Lorenzo a Merse (9)
  • San Quirico d'Orcia (38)
  • Sant'Alberto (1)
  • Sarteano (60)
  • Siena (486)
  • Sinalunga (143)
  • Sovicille (70)
  • Strove (6)
  • Tognazza (2)
  • Torre A Castello (3)
  • Torrita di Siena (36)
  • Trequanda (22)
  • Vergelle (15)
  • Ville di Corsano (22)
  • Vivo d'Orcia (5)
  • Volte Basse (2)

More

Less

Also consider

Coastal Cottages
222 properties
Apartments Sardinia
478 properties
Apartments Tuscany
3181 properties
Apartments Lake Garda Area
103 properties
Apartments Lake Como Area
494 properties
Apartments Sicily
634 properties
Villas Siena
504 properties
Villas San Gimignano
426 properties
Villas Montepulciano
285 properties
Casole d'Elsa
182 properties
Colle di Val d'Elsa
181 properties
Poggibonsi
165 properties
Gaiole in Chianti
162 properties
Villas Pienza
160 properties
Sinalunga
156 properties
Castelnuovo Berardenga
156 properties
Villas Montalcino
152 properties
Villas Castellina In Chianti
144 properties
Asciano
123 properties
Rapolano Terme
103 properties
Payment Protection
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

4,171 Holiday homes

32

Montepulciano / Valiano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Ask about pets

 …see more

from £69 / night

£388 - £432 / week

Book View

from £69 / night

29

Province of Siena / Palazzone

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

 …see more

from £216 / night

£604 / week

Book View

from £216 / night

5

Montepulciano / Valiano

2 3 2 nights min

  • 2 bedrooms
  • Sleeps 3
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £113 / night

£656 / week

Book View

from £113 / night

39

Villa Afrodite - Pienza villa sleeps 10

Province of Siena / Pienza

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Private garden
<br>Villa Afrodite – Pienza – Tuscany<br>5 Double Bedrooms – Pool<br>Villa Afrodite lays on top of a hill that leads to the Nobile vineyards of Montepulciano and on the other hand to the hills of the Val d'Orcia; from the villa Afrodite you  …see more

from £493 / night

£3449 - £4138 / week

Book View

from £493 / night

12

Il Casale di Piera - Castiglione D'Orcia villa sleeps 25

Province of Siena / Castiglione D'Orcia

8 25 Min stay varies

  • 8 bedrooms
  • Sleeps 25
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
The farm 'Moro Fiacchi' that hosts "Il Casale di Piera" holiday house, is a typical Tuscan country mansion from the XVII century, with a spectacular pool overlooking the boundless valley, it sits in the very heart of the Val D'Orcia Artistic, Na  …see more

from £308 / night

£2156 - £4311 / week

Book View

from £308 / night

28

Radicondoli / Belforte

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly

 …see more

from £116 / night

£807 / week

Book View

from £116 / night

(3) Excellent 

43

Podere La Casina - Radicondoli villa sleeps 6

Province of Siena / Radicondoli

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 65 km
  • Child friendly
  • Pet friendly
The old country villa is composed by a large sitting-room with a huge traditional fireplace and a big sofa, a dining-room provided with a big table for 8 people, two double bedrooms, each with its own private bathroom, a studio with two single beds, a kitchen with store  …see more

from £173 / night

£1035 / week

Book View

from £173 / night

72

55839-Holiday house Val d'Orci - Celle sul Rigo villa sleeps 15

San Casciano dei Bagni / Celle sul Rigo

7 15 7 nights min

  • 7 bedrooms
  • Sleeps 15
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Between San Casciano dei Bagni, in the southern part of the province of Siena, and the hills around Viterbo, this wonderful country house, recently restored, allows you a fantastic view of the valley around and of Mount Amiata. The quality of the restoration is excellen  …see more

from £192 / night

£1344 - £1939 / week

Enquire View

from £192 / night

10

34183-Apartment Chianti - Radda in Chianti apartment sleeps 8

Province of Siena / Radda in Chianti

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Ancient farm located in the heart of Chianti (Castellina in Chianti) near Siena, a few kilometers from Florence. It offers 6 really nice apartments, a swimming pool with sun terrace (12 x 6 mt) open in summer, a tasting room (medieval cellar) handicap accessible and equ  …see more

from £102 / night

£708 / week

Enquire View

from £102 / night

100

Casa Bardini - Archi - Sinalunga apartment sleeps 5

Province of Siena / Sinalunga

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
 Archi is a 73 sqm apartment located in the first floor of the farmhouse. It has a large sitting-dining room, a kitchenette and a cozy fireplace, a double sofa-bed, a bathroom with a shower and a double bedroom with ensuite bathroom with a hydromassage shower.It is  …see more

from £113 / night

£630 - £863 / week

Enquire View

from £113 / night

18

Valiano - 15663001 - Valiano farmhouse sleeps 10

Montepulciano / Valiano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Beautiful 5-hectare estate in Tuscany, a villa for wedding celebration and holidays, comprising a farmhouse of 140 m2 and an outbuilding of 60 m2 which have been skilfully restored and turned into a delightful independent villa offering tastefully and refined furnished  …see more

from £159 / night

£1113 - £2190 / week

Enquire View

from £159 / night

7

Mimosa Apartment - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
The Terrarossa farm holiday resort is deep in the stunning hills around Montepulciano.It is part of an ancient country estate counting 130 acrwes land, where with respect for the land and its natural balance wheat, sunflowers and, above all, the vines for Vino Nobile di  …see more

from £130 / night

£785 / week

Book View

from £130 / night

100

Casa Bardini - Limonaia - Sinalunga apartment sleeps 3

Province of Siena / Sinalunga

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
 Limonaia is a cozy apartment in Sinalunga on two levels. On the ground floor there is a pergola with garden furniture, a sitting-dining room with a kitchenette and a french sofa-bed, and the bathroom with a shower. In the mezzanine, reachable by a staircase there  …see more

from £95 / night

£500 - £690 / week

Enquire View

from £95 / night

9

Holiday House Sarteano - Sarteano house sleeps 4

Province of Siena / Sarteano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Borgo Fastelli in its 1765 Catasto Leopoldino entry (the local land registry of the time) is an historical abode which has been towering over the Val d'Orcia for centuries. Located in the western part of Monte Cetona, it has a unique view of the valley below, which  …see more

from £173 / night

£1035 / week

Book View

from £173 / night

19

Antico Borgo Poggiarello - Monteriggioni house sleeps 30

Province of Siena / Monteriggioni

15 30 Min stay varies

  • 15 bedrooms
  • Sleeps 30
  • Min stay varies
  • Nearest beach 84 km
  • Swimming pool
  • Child friendly
The structure consists of apartments (surrounded by 30.000 meters of olive trees and wood), charmingly furnished in the old style of Tuscany and telephone line for internet connection. From May 1st until September 15th it's possible to enjoy the swimming pool of 1  …see more

Pricing unknown

Book View

Pricing unknown

18

San Gimignano / Ulignano

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £113 / night

£768 / week

Book View

from £113 / night

24

Tuscany 5 bedroom villa. Gym. Archery field. Golf. - Cetona villa sleeps 9

Province of Siena / Cetona

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Child friendly
This is a fantastic 5 bedroom villa in Tuscany. Situated on a hill near Cetona and with a large private garden measuring 10,000 square metres, this is a property full of on site amenities including a private swimming pool (12 x 6 metres), archery field, golf area with 2  …see more

from £339 / night

£2371 - £3233 / week

Book View

from £339 / night

20

126514003 - Colle Di Val De - Poggibonsi hotel apartment sleeps 4

Province of Siena / Poggibonsi

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
The Ancient Borgo San Lorenzo, purchased in 1990 by the Bandini family and restored with great care over the years, now back to its original vocation: the old farmhouse, the barn, the granary, the Owner House have now become pleasant and elegant homes for guests with a  …see more

from £113 / night

£785 - £1268 / week

Enquire View

from £113 / night

26

Province of Siena / Cetona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £216 / night

£1509 / week

Book View

from £216 / night

20

126514002 - Colle Di Val De - Poggibonsi hotel apartment sleeps 10

Province of Siena / Poggibonsi

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
The Ancient Borgo San Lorenzo, purchased in 1990 by the Bandini family and restored with great care over the years, now back to its original vocation: the old farmhouse, the barn, the granary, the Owner House have now become pleasant and elegant homes for guests with a  …see more

from £169 / night

£1177 - £2113 / week

Enquire View

from £169 / night

10

15462-Apartment Chianti - Castellina In Chianti apartment sleeps 5

Province of Siena / Castellina In Chianti

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Three Bedroom Ground Floor Apartment Chianti Castellina is a charming apartment, part of a farmhouse situated in beautiful Chianti countryside. The apartment opens onto its own lovely shaded terrace with table and chairs for dining al fresco, and there is more space fo  …see more

from £50 / night

£344 - £384 / week

Enquire View

from £50 / night

(5) Excellent 

18

Province of Siena / San Gimignano

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £100 / night

£694 / week

Book View

from £100 / night

24

Province of Siena / San Casciano dei Bagni

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

 …see more

from £345 / night

£1294 - £2845 / week

Book View

from £345 / night

(1) Excellent 

36

Poggibonsi / Staggia

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £518 / night

£3621 - £4828 / week

Enquire View

from £518 / night

24

126514001 - Colle Di Val De - Poggibonsi hotel apartment sleeps 5

Province of Siena / Poggibonsi

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
The Ancient Borgo San Lorenzo, purchased in 1990 by the Bandini family and restored with great care over the years, now back to its original vocation: the old farmhouse, the barn, the granary, the Owner House have now become pleasant and elegant homes for guests with a  …see more

from £113 / night

£785 - £1268 / week

Enquire View

from £113 / night

8

15397-Apartment San Gimignano - Montecchio apartment sleeps 4

Province of Siena / Montecchio

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Two Bedroom First Floor Apartment San Gimignano A winding avenue of cypress trees leads apartment Gina on the ‘La Fattoria estate’. Situated in a fantastic elevated position above San Gimignano, there are lovely views of the countryside and the medieval town across  …see more

from £66 / night

£460 - £646 / week

Enquire View

from £66 / night

4

San Gimignano / Ulignano

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

Pricing unknown

Book View

Pricing unknown

17

Monticchiello - 57318001 - Pienza farmhouse sleeps 4

Province of Siena / Pienza

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Welcoming farmhouse situated in panoramic location in the beautiful area of Val D’Orcia. This property comprises 4 units (one is occupied by the owners) and offers a well-groomed garden, a private furnished area for all of the 3 apartments and a nice pool (with Jacuzz  …see more

from £69 / night

£394 - £689 / week

Enquire View

from £69 / night

20

126514008 - Colle Di Val De - Poggibonsi hotel apartment sleeps 2

Province of Siena / Poggibonsi

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
The Ancient Borgo San Lorenzo, purchased in 1990 by the Bandini family and restored with great care over the years, now back to its original vocation: the old farmhouse, the barn, the granary, the Owner House have now become pleasant and elegant homes for guests with a  …see more

from £100 / night

£694 - £1026 / week

Enquire View

from £100 / night

20

Asciano / Crete Senesi

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly

 …see more

Pricing unknown

Book View

Pricing unknown

17

Apartment bruco - Colle di Val d'Elsa farmhouse sleeps 4

Province of Siena / Colle di Val d'Elsa

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
The farm house Verniano is a petting farm and an organic farm, a family immersed in the typical rural Tuscan landscape. Perfect for families, couples and groups of friends.The farm consists of five apartments, obtained from recent restructuring of the small village of &  …see more

Pricing unknown

Book View

Pricing unknown

100

Emma - Glicine - Bagno Vignoni apartment sleeps 6

Province of Siena / Bagno Vignoni

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Cortile, on the first floor of the house is a large apartment with space for up to six guests to sleep comfortably. There is a double bedroom and a second bedroom with twin beds. Both are charming rooms like those in all the other apartments, with a traditional country  …see more

from £104 / night

£604 - £845 / week

Enquire View

from £104 / night

24

Podere la Marronaia Yellow 2p - San Gimignano farmhouse sleeps 2

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
Podere la Marronaia is a small and welcoming farmhouse situated on a small hill among vineyards and olive groves, close to the historical centre of San Gimignano (2km). The central part of this historical building is the watching tower built in 1200 ad as part of the c  …see more

Pricing unknown

Book View

Pricing unknown

45

Province of Siena / Vergelle

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Ask owner if suitable for children
  • Ask about pets

 …see more

from £121 / night

£845 - £1026 / week

Enquire View

from £121 / night

(6) Excellent 

24

Chic Tuscan villa in the heart of the countryside, staffed property with shared pool and private garden space, sleeps 4 - Monteguidi farmhouse sleeps 4

Casole d'Elsa / Monteguidi

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 68 km
  • Swimming pool
  • Child friendly
Very chic villa on the ground floor of the smaller farmhouse in a bigger setting in the heart of the Tuscan countryside. Great for a family of four or for two couples of friends. Large master bedroom with canopy bed and a second bedroom with twin beds, which can be com  …see more

from £99 / night

£690 / week

Book View

from £99 / night

11

Province of Siena / Ville di Corsano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

Pricing unknown

Book View

Pricing unknown

9

Casale Oliveta - Pettirosso - Poggibonsi apartment sleeps 2

Province of Siena / Poggibonsi

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Private garden
Casale Oliveta is located in a little hamlet with a few houses up in the hills. Altthough only 3 km distant from the town of Poggibonsi where you can also find supermarkets, banks, cafés, pubs, cinemas, a theatre and a railway station, the hamlet is located in a comple  …see more

from £19 / night

£1916 / week

Enquire View

from £19 / night

44

CHARMING ANCIENT COUNTRY HOUSE, MONTALCINO, SIENA - Montalcino house sleeps 26

Province of Siena / Montalcino

12 26 7 nights min

  • 12 bedrooms
  • Sleeps 26
  • 7 nights min
  • Child friendly
  • Pet friendly
Up to 27 guests! An enchanted place… FATTORIA PIAN DELL’ASSO is a beautiful XVI century villa situated in the wonderful senese countryside a few km’s from Montalcino, in the natural park of the Val d' Orcia, a precious architectural and natural context. Here you  …see more

from £616 / night

£4311 - £4837 / week

Book View

from £616 / night

31

Villa Moro - San Giovanni d'Asso villa sleeps 10

Province of Siena / San Giovanni d'Asso

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa Moro is part of a vineyard estate set on a panoramic hillside overlooking the broad valley of farmland near an ancient village in central Siena Province. Villa Moro is an exceptionally well furnished home, the owner of the vineyard lived here for many years and l  …see more

from £832 / night

£5819 / week

Book View

from £832 / night

21

Siena / Isola d'Arbia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £67 / night

£465 - £550 / week

Book View

from £67 / night

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page