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

View larger map

Price per night

£212 Average

Price per night

to

Bedrooms

Bathrooms

Location

  • Italy
  • Tuscany
  • Province of Siena

Location

  • All locations
  • Abbadia San Salvatore (6)
  • Asciano (129)
  • Bagni di San Filippo (2)
  • Bagno Vignoni (16)
  • Brenna (6)
  • Buonconvento (58)
  • Campiglia d'Orcia (2)
  • Casciano (2)
  • Casole d'Elsa (159)
  • Castellina In Chianti (126)
  • Castelmuzio (14)
  • Castelnuovo Berardenga (152)
  • Castiglione D'Orcia (45)
  • Cetona (72)
  • Chianciano Terme (38)
  • Chiusdino (33)
  • Chiusi (35)
  • Colle di Val d'Elsa (122)
  • Europe (7)
  • Gaiole in Chianti (164)
  • La Piazza (1)
  • Le Piazze (9)
  • Lucarelli (2)
  • Montalcino (122)
  • Montecchio (7)
  • Montepulciano (250)
  • Monteriggioni (93)
  • Monteroni d'Arbia (42)
  • Monticiano (29)
  • Montisi (22)
  • Murlo (28)
  • Orgia (5)
  • Palazzone (12)
  • Petroio (1)
  • Piancastagnaio (8)
  • Pienza (151)
  • Pievasciata (2)
  • Pievescola (10)
  • Poggibonsi (139)
  • Radda in Chianti (65)
  • Radicofani (52)
  • Radicondoli (89)
  • Rapolano Terme (77)
  • Rocca d'Orcia (8)
  • Rosia (9)
  • San Casciano dei Bagni (49)
  • San Gimignano (408)
  • San Giovanni d'Asso (49)
  • San Lorenzo a Merse (2)
  • San Quirico d'Orcia (13)
  • Sarteano (51)
  • Siena (459)
  • Sinalunga (128)
  • Sovicille (91)
  • Strove (5)
  • Torre A Castello (2)
  • Torrita di Siena (32)
  • Trequanda (18)
  • Vergelle (12)
  • Ville di Corsano (12)
  • Vivo d'Orcia (2)
  • Volte Basse (1)

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
463 properties
Villas San Gimignano
409 properties
Villas Montepulciano
250 properties
Gaiole in Chianti
165 properties
Villas Casole d'Elsa
159 properties
Villas Castelnuovo Berardenga
153 properties
Villas Pienza
151 properties
Villas Poggibonsi
139 properties
Asciano
136 properties
Villas Castellina In Chianti
129 properties
Villas Sinalunga
128 properties
Apartments Colle di Val d'Elsa
122 properties
Villas Montalcino
122 properties
Villas Monteriggioni
93 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

3,761 Holiday homes

Travellers going to Province of Siena are booking June dates now. Secure your holiday home today and have the perfect trip.

1 / 14

Radda in Chianti holiday home rental

Province of Siena / Radda in Chianti

2 4 7 nights min stay

House / 2 bedrooms / sleeps 4 / 7 nights min stay

Add to shortlist

from £191 / night

£1149 / week

Enquire

from £191 / night

1 / 19

Holiday farmhouse with swimming pool in Casole d'Elsa

Province of Siena / Casole d'Elsa

6 12 7 nights min stay

Farmhouse / 6 bedrooms / sleeps 12 / 7 nights min stay

Add to shortlist

from £877 / night

£6139 - £11462 / week

Enquire

from £877 / night

1 / 17

Holiday farmhouse with shared pool in Vagliagli

Castelnuovo Berardenga / Vagliagli

2 4 3 nights min stay

Farmhouse / 2 bedrooms / sleeps 4 / 3 nights min stay

Add to shortlist

from £109 / night

£760 - £1088 / week

Enquire

from £109 / night

Featured properties

1 / 19

Holiday farmhouse in Rosia

Province of Siena / Rosia

3 6 Min stay varies

Farmhouse / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £140 / night

£575 - £637 / week

Enquire

from £140 / night

1 / 20

Holiday farmhouse with shared pool in Casole d'Elsa

Province of Siena / Casole d'Elsa

4 8 7 nights min stay

Farmhouse / 4 bedrooms / sleeps 8 / 7 nights min stay

Add to shortlist

from £113 / night

£789 - £1445 / week

Enquire

from £113 / night

1 / 20

Holiday home in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

5 10 Min stay varies

House / 5 bedrooms / sleeps 10 / Min stay varies

Add to shortlist

from £415 / night

£2904 - £3804 / week

Enquire

from £415 / night

(1) Excellent 

1 / 11

Serre di Rapolano holiday farmhouse rental

Rapolano Terme / Serre di Rapolano

1 2 3 nights min stay

Farmhouse / 1 bedroom / sleeps 2 / 3 nights min stay

Add to shortlist

from £66 / night

£427 - £505 / week

Enquire

from £66 / night

1 / 20

Holiday farmhouse with shared pool in Province of Siena

Tuscany / Province of Siena

3 6 7 nights min stay

Farmhouse / 3 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £189 / night

£1321 - £1787 / week

Enquire

from £189 / night

1 / 21

Holiday apartment with shared pool in Casole d'Elsa

Province of Siena / Casole d'Elsa

1 2 7 nights min stay

Apartment / 1 bedroom / sleeps 2 / 7 nights min stay

Add to shortlist

from £51 / night

£356 - £507 / week

Enquire

from £51 / night

1 / 20

Rigomagno holiday farmhouse rental

Sinalunga / Rigomagno

3 7 Min stay varies

Farmhouse / 3 bedrooms / sleeps 7 / Min stay varies

Add to shortlist

from £247 / night

£1437 - £1787 / week

Enquire

from £247 / night

1 / 20

Holiday farmhouse in Province of Siena

Tuscany / Province of Siena

5 12 1 night min stay

Farmhouse / 5 bedrooms / sleeps 12 / 1 night min stay

Add to shortlist

from £194 / night

£1244 - £1477 / week

Enquire

from £194 / night

1 / 20

Holiday farmhouse accommodation

Province of Siena / Monticiano

3 8 7 nights min stay

Farmhouse / 3 bedrooms / sleeps 8 / 7 nights min stay

Add to shortlist

from £130 / night

£909 - £1591 / week

Enquire

from £130 / night

1 / 16

Holiday farmhouse with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 6 7 nights min stay

Farmhouse / 3 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £319 / night

£2231 - £3500 / week

Enquire

from £319 / night

1 / 9

Bettolle holiday apartment rental

Sinalunga / Bettolle

2 5 Min stay varies

Apartment / 2 bedrooms / sleeps 5 / Min stay varies

Add to shortlist

from £94 / night

£654 - £1508 / week

Enquire

from £94 / night

1 / 9

Bettolle holiday apartment rental

Sinalunga / Bettolle

2 4 Min stay varies

Apartment / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £108 / night

£754 - £1185 / week

Enquire

from £108 / night

1 / 20

Holiday home in Murlo

Province of Siena / Murlo

1 7 nights min stay

House / sleeps 1 / 7 nights min stay

Add to shortlist

from £111 / night

£773 - £980 / week

Enquire

from £111 / night

(1) Excellent 

1 / 10

Villa letting in Sovicille

Province of Siena / Sovicille

2 4 4 nights min stay

Villa / 2 bedrooms / sleeps 4 / 4 nights min stay

Add to shortlist

from £107 / night

£641 - £1320 / week

Enquire

from £107 / night

1 / 20

Holiday home in Chiusdino

Province of Siena / Chiusdino

1 7 nights min stay

House / sleeps 1 / 7 nights min stay

Add to shortlist

from £247 / night

£1725 - £2621 / week

Enquire

from £247 / night

1 / 20

Holiday home in Murlo

Province of Siena / Murlo

1 7 nights min stay

House / sleeps 1 / 7 nights min stay

Add to shortlist

from £121 / night

£842 - £1152 / week

Enquire

from £121 / night

(1) Excellent 

1 / 15

Sovicille holiday home rental

Province of Siena / Sovicille

2 4 Min stay varies

House / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £119 / night

£712 - £1464 / week

Enquire

from £119 / night

1 / 20

Holiday farmhouse with shared pool in Buonconvento

Buonconvento / Chiusure

2 6 Min stay varies

Farmhouse / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £113 / night

£660 - £1282 / week

Enquire

from £113 / night

1 / 28

Holiday apartment with shared pool in Casole d'Elsa

Province of Siena / Casole d'Elsa

2 4 7 nights min stay

Apartment / 2 bedrooms / sleeps 4 / 7 nights min stay

Add to shortlist

from £77 / night

£534 - £765 / week

Enquire

from £77 / night

1 / 20

Holiday farmhouse with swimming pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

5 8 7 nights min stay

Farmhouse / 5 bedrooms / sleeps 8 / 7 nights min stay

Add to shortlist

from £413 / night

£2885 - £4196 / week

Enquire

from £413 / night

1 / 15

Farmhouse rental in Sarteano with shared pool

Province of Siena / Sarteano

2 6 Min stay varies

Farmhouse / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £109 / night

£497 - £560 / week

Enquire

from £109 / night

1 / 26

Holiday home with swimming pool in Monteriggioni

Province of Siena / Monteriggioni

2 4 7 nights min stay

House / 2 bedrooms / sleeps 4 / 7 nights min stay

Add to shortlist

from £83 / night

£577 - £1352 / week

Enquire

from £83 / night

1 / 48

Holiday villa with shared pool in Monteriggioni

Province of Siena / Monteriggioni

2 4 4 nights min stay

Villa / 2 bedrooms / sleeps 4 / 4 nights min stay

Add to shortlist

from £72 / night

£500 - £654 / week

Enquire

from £72 / night

1 / 37

Holiday home rental

Province of Siena / Radicofani

5 12 Min stay varies

House / 5 bedrooms / sleeps 12 / Min stay varies

Add to shortlist

from £484 / night

£3385 / week

Enquire

from £484 / night

1 / 18

Holiday farmhouse rental

Province of Siena / San Casciano dei Bagni

2 7 7 nights min stay

Farmhouse / 2 bedrooms / sleeps 7 / 7 nights min stay

Add to shortlist

from £87 / night

£606 - £855 / week

Enquire

from £87 / night

1 / 24

Holiday villa in Staggia Senese

Poggibonsi / Staggia Senese

6 12 Min stay varies

Villa / 6 bedrooms / sleeps 12 / Min stay varies

Add to shortlist

from £577 / night

£4039 - £5385 / week

Enquire

from £577 / night

(10) Excellent 

1 / 24

Holiday cottage with swimming pool, golf nearby in Casole d'Elsa

Province of Siena / Casole d'Elsa

2 4 6 nights min stay

Cottage / 2 bedrooms / sleeps 4 / 6 nights min stay

Add to shortlist

from £104 / night

£616 - £885 / week

Enquire

from £104 / night

1 / 24

Monticiano holiday villa rental

Province of Siena / Monticiano

8 18 Min stay varies

Villa / 8 bedrooms / sleeps 18 / Min stay varies

Add to shortlist

from £810 / night

£5225 - £5630 / week

Enquire

from £810 / night

(1) Excellent 

1 / 24

Asciano holiday home rental

Province of Siena / Asciano

5 Min stay varies

House / sleeps 5 / Min stay varies

Add to shortlist

from £117 / night

£703 - £973 / week

Enquire

from £117 / night

1 / 44

Holiday villa with shared pool in Monteriggioni

Province of Siena / Monteriggioni

2 4 4 nights min stay

Villa / 2 bedrooms / sleeps 4 / 4 nights min stay

Add to shortlist

from £55 / night

£385 - £500 / week

Enquire

from £55 / night

1 / 15

Holiday farmhouse with shared pool in Rigomagno

Sinalunga / Rigomagno

2 4 Min stay varies

Farmhouse / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £132 / night

£769 - £1119 / week

Enquire

from £132 / night

1 / 20

Holiday home with swimming pool in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

7 16 Min stay varies

House / 7 bedrooms / sleeps 16 / Min stay varies

Add to shortlist

from £544 / night

£3804 - £4806 / week

Enquire

from £544 / night

1 / 20

Holiday home with shared pool in San Gusme

Castelnuovo Berardenga / San Gusme

2 4 Min stay varies

House / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £78 / night

£467 - £933 / week

Enquire

from £78 / night

1 / 17

Holiday farmhouse in San Casciano dei Bagni

Province of Siena / San Casciano dei Bagni

1 4 Min stay varies

Farmhouse / 1 bedroom / sleeps 4 / Min stay varies

Add to shortlist

from £86 / night

£377 - £590 / week

Enquire

from £86 / night

1 / 20

Holiday home in Buonconvento

Province of Siena / Buonconvento

1 7 nights min stay

House / sleeps 1 / 7 nights min stay

Add to shortlist

from £124 / night

£863 - £1235 / week

Enquire

from £124 / night

1 / 20

Holiday home in Buonconvento

Province of Siena / Buonconvento

1 7 nights min stay

House / sleeps 1 / 7 nights min stay

Add to shortlist

from £77 / night

£538 - £828 / week

Enquire

from £77 / night

1 / 20

Holiday home in Monteriggioni

Province of Siena / Monteriggioni

1 7 nights min stay

House / sleeps 1 / 7 nights min stay

Add to shortlist

from £84 / night

£587 - £1100 / week

Enquire

from £84 / night

1 / 11

Monteriggioni holiday home rental

Province of Siena / Monteriggioni

2 4 7 nights min stay

House / 2 bedrooms / sleeps 4 / 7 nights min stay

Add to shortlist

from £162 / night

£1131 - £1546 / week

Enquire

from £162 / night

1 / 100

Sinalunga holiday apartment rental

Province of Siena / Sinalunga

1 4 Min stay varies

Apartment / 1 bedroom / sleeps 4 / Min stay varies

Add to shortlist

from £100 / night

£562 - £770 / week

Enquire

from £100 / night

(9) Very Good 

1 / 32

Holiday home with shared pool in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

2 5 3 nights min stay

House / 2 bedrooms / sleeps 5 / 3 nights min stay

Add to shortlist

from £162 / night

£1131 - £1546 / week

Enquire

from £162 / night

1 / 20

Holiday apartment with shared pool in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

2 4 Min stay varies

Apartment / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £80 / night

£560 / week

Enquire

from £80 / night

1 / 100

Holiday apartment with shared pool in Sinalunga

Province of Siena / Sinalunga

2 6 Min stay varies

Apartment / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £116 / night

£693 - £962 / week

Enquire

from £116 / night

(1) Excellent 

1 / 17

Holiday villa in Monteriggioni

Province of Siena / Monteriggioni

2 4 4 nights min stay

Villa / 2 bedrooms / sleeps 4 / 4 nights min stay

Add to shortlist

from £151 / night

£908 - £1211 / week

Enquire

from £151 / night

(5) Excellent 

1 / 25

Holiday home with shared pool in Monteriggioni

Province of Siena / Monteriggioni

6 12 7 nights min stay

House / 6 bedrooms / sleeps 12 / 7 nights min stay

Add to shortlist

from £470 / night

£3284 - £3960 / week

Enquire

from £470 / night

1 / 20

Holiday farmhouse with shared pool in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

1 4 7 nights min stay

Farmhouse / 1 bedroom / sleeps 4 / 7 nights min stay

Add to shortlist

from £142 / night

£990 / week

Enquire

from £142 / night

1 / 18

Holiday farmhouse with swimming pool in Montisi

Province of Siena / Montisi

2 6 Min stay varies

Farmhouse / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £140 / night

£816 - £1166 / week

Enquire

from £140 / night

1 / 24

Sarteano holiday home rental

Province of Siena / Sarteano

4 8 Min stay varies

House / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £425 / night

£2550 - £3400 / week

Enquire

from £425 / 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