Private Holiday Homes in Province of Siena

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Province of Siena holiday homes

Lanai

Il Palazzetto

Il Palazzetto
Siena
9.6 out of 10, Exceptional, (7 reviews)
"Endroit agréable, idéal pour visiter Sienne à moins de 10mns en voiture et rayonner dans la région."
France
Francois
Il Palazzetto
Premium bedding, down duvets, in-room safe, desk

Borgo Argiano

Borgo Argiano
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (83 reviews)
"Amazing staff, clean room, amazing pool!"
United States
Blake
Borgo Argiano
Exterior

Borgo Villa Certano

Borgo Villa Certano
Siena
Borgo Villa Certano
Outdoor pool

Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.0 out of 10, Wonderful, (8 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is RM466
RM536 total
includes taxes & fees
29 Jun - 30 Jun
Casa Vacanze Le Case
Flat-screen TV, fireplace

Casale di Villore

Casale di Villore
Poggibonsi
10.0 out of 10, Exceptional, (2 reviews)
"Fantastic property. Can’t wait to return next year. "
Canada
Owen
Casale di Villore
Front of property

Zampugna

Zampugna
Trequanda
9.2 out of 10, Wonderful, (5 reviews)
"Beautiful and host is great!"
United States
August
The price is RM1,975
RM2,187 total
includes taxes & fees
24 Jun - 25 Jun
Zampugna
Front of property

Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
Agriturismo La Ferrozzola
4 bedrooms, iron/ironing board, free WiFi, bed sheets

Chianti Classico Home Panoramic View

Chianti Classico Home Panoramic View
Castellina in Chianti
Chianti Classico Home Panoramic View
Exterior

Tranquil Stay in Montepulciano

Tranquil Stay in Montepulciano
Montepulciano
Tranquil Stay in Montepulciano
Aerial view

Casa La Cedrina Pool Lornano

Casa La Cedrina Pool Lornano
Monteriggioni
Casa La Cedrina Pool Lornano
Pool

Lovely Home Between Volterra and San Gimignano

Lovely Home Between Volterra and San Gimignano
San Gimignano City Centre
Lovely Home Between Volterra and San Gimignano
Exterior

Holiday Home in Tuscany With Pool

Holiday Home in Tuscany With Pool
Montepulciano
Holiday Home in Tuscany With Pool
Exterior

Chianti Hillside Farmhouse

Chianti Hillside Farmhouse
Radda in Chianti
10.0 out of 10, Exceptional, (1 review)
"The property was in a beautiful location with lots of room for 6 adults traveling together."
Canada
Allison
Chianti Hillside Farmhouse
Exterior

Amelia House Private Pool Casole Elsa Monti

Amelia House Private Pool Casole Elsa Monti
Casole d'Elsa
Amelia House Private Pool Casole Elsa Monti
Pool

Farmhouse in Buonconvento

Farmhouse in Buonconvento
Buonconvento
10.0 out of 10, Exceptional, (2 reviews)
"Detailed and good instructions were received before arriving. The host speaks very well English and is very helpful. "
Denmark
Haiping
Farmhouse in Buonconvento
Balcony

Pretty Farmhouse With Terrace

Pretty Farmhouse With Terrace
Radda in Chianti
7.0 out of 10, Good, (2 reviews)
"Beautiful views out in the Tuscan countryside in a vineyard. If you are looking for peace and quiet, this place is wonderful. "
United States
Rick
Pretty Farmhouse With Terrace
Pool

Farmhouse in Tuscany Near Siena & Hot Springs

Farmhouse in Tuscany Near Siena & Hot Springs
Castelnuovo Berardenga
Farmhouse in Tuscany Near Siena & Hot Springs
Property grounds

La Terrazza, Historic Tuscan Stone Residence With Garden and Terrace in Cetona

La Terrazza, Historic Tuscan Stone Residence With Garden and Terrace in Cetona
Cetona
10.0 out of 10, Exceptional, (1 review)
"Marco and Margherita were warm and welcoming hosts! We thoroughly enjoyed our time in the beautiful village of Cetona and the surrounding areas. The home was a lovely decorated 3 levels with comfortable beds and all the amenities needed. There is also a lovely terrace garden up top to enjoy. Marco and Margherita gave clear directions to the property. Of note- the home sits on 3 levels and has steep winding staircases which we were totally fine with but may be of note for those with...
Canada
DEENA
La Terrazza, Historic Tuscan Stone Residence With Garden and Terrace in Cetona
Room

Country House a Casole d Elsa ID 451

Country House a Casole d Elsa ID 451
Casole d'Elsa
Country House a Casole d Elsa ID 451
Pool

Mansion Stay With Scenic Views

Mansion Stay With Scenic Views
Siena
Mansion Stay With Scenic Views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Province of Siena Hotel Reviews

Hotel Italia

Hotel Italia

10/10 Excellent
"Muy amables en todo momento. De hecho, tuvimos un detalle con la habitación, y nos ofrecieron otra opción que se adaptara a nuestras necesidades. Muy agradecidos. Y el desayuno muy variado y delicioso."
Maria 3-night trip
Posted 12 hours ago
Hotel Italia

Find out more about Province of Siena

Province of Siena Private Holiday Homes information

Number of reviews
120
Accommodation
144 Private Holiday Homes
Lowest Price
RM536
Highest Price
RM2,187

Explore a world of travel with Expedia