A historic town with a prominent tower and a rainbow arching over it.

Holiday Homes in Province of Siena

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Province of Siena holiday homes

A bedroom with a large bed, a wooden ceiling, and a brick archway.

1. Borgo Argiano

Borgo Argiano
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (88 reviews)
"Amazing staff, clean room, amazing pool!"
United States
Blake
Borgo Argiano
A table set outdoors with food, wine, and a view of a countryside landscape.

2. 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
A hallway leading to an outdoor patio with a table and chairs, framed artwork on the walls, and a rustic ceiling.

3. Casale di Villore

Casale di Villore
Poggibonsi
10.0 out of 10, Exceptional, (4 reviews)
"Fantastic property. Can’t wait to return next year. "
Canada
Owen
Casale di Villore
A stone building with multiple windows and a chimney.

4. 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
An outdoor swimming pool with lounge chairs and umbrellas, surrounded by stone buildings and trees.

5. Tasteful Countryside Stay

Tasteful Countryside Stay
Montalcino
Tasteful Countryside Stay
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

6. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (13 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
Casa Vacanze Le Case
A large, historic building with multiple floors and a courtyard, surrounded by lush greenery and rolling hills.

7. Borgo Villa Certano

Borgo Villa Certano
Siena
Borgo Villa Certano
A bedroom with a bed, a chair, a table, and a window with curtains.

8. Chianti Classico Home Panoramic View

Chianti Classico Home Panoramic View
Castellina in Chianti
Chianti Classico Home Panoramic View
A stone building with a tiled roof, surrounded by dry grass and trees, set in a hilly landscape.

9. Zampugna

Zampugna
Trequanda
9.2 out of 10, Wonderful, (5 reviews)
"Beautiful and host is great!"
United States
August
Zampugna
A historic building with a bell tower, surrounded by lush greenery and hills.

10. Casa di Giulio

Casa di Giulio
Castiglione d'Orcia
Casa di Giulio
A rectangular swimming pool with a clear blue water, surrounded by lounge chairs and umbrellas, set against a backdrop of olive trees and a distant town.

11. Agriturismo La Torretta

Agriturismo La Torretta
Siena
8.6 out of 10, Excellent, (4 reviews)
"Täysin uudet siistit huoneet. Runsas aamupala. Rauhallinen ympäristö. Wi-Fi ei toiminut. "
Finland
Sonja
Agriturismo La Torretta
A stone building with a tiled roof, surrounded by greenery and trees.

12. 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
A stone staircase leading up to a building with a rustic appearance, surrounded by lush greenery and white flowers.

13. 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
A covered patio area with outdoor seating, a stone floor, and a view of the garden and trees.

14. Tranquil Stay in Montepulciano

Tranquil Stay in Montepulciano
Montepulciano
Tranquil Stay in Montepulciano
A stone building with a wooden ceiling, a brick pathway, and a view of trees and a distant landscape.

15. Amelia House Private Pool Casole Elsa Monti

Amelia House Private Pool Casole Elsa Monti
La Corsina
8.0 out of 10, Very good, (1 review)
Amelia House Private Pool Casole Elsa Monti
A wooden deck with a wicker chair and a table set with wine glasses and a fruit plate.

16. Rustic Escape With Pool

Rustic Escape With Pool
Castelnuovo Berardenga
8.0 out of 10, Very good, (1 review)
Rustic Escape With Pool
A covered patio area with outdoor seating, a stone floor, and a view of the garden and trees.

17. Holiday Home in Tuscany With Pool

Holiday Home in Tuscany With Pool
Montepulciano
Holiday Home in Tuscany With Pool
An outdoor dining area with a table set for two, overlooking a vineyard.

18. 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
A villa with a stone facade, terracotta roof tiles, and a central courtyard with a swimming pool.

19. Casa La Cedrina Pool Lornano

Casa La Cedrina Pool Lornano
Monteriggioni
Casa La Cedrina Pool Lornano
A pool with a water feature, blue lounge chairs, and a pink umbrella.

20. 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.
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Top Province of Siena Hotel Reviews

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

10/10 Excellent
"Great location, nice vineyards right out the door, lots of great restaurants nearby."
Lisa 2-night trip
Posted 7 hours ago
Precise Tale Poggio Alla Sala

Find out more about Province of Siena

Province of Siena Holiday Homes information

Number of reviews
130
Accommodation
191 Holiday Homes
Lowest Price
Highest Price