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

Private Holiday Homes in Province of Siena

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

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, (91 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 large, historic building with multiple floors and a courtyard, surrounded by lush greenery and rolling hills.

3. Borgo Villa Certano

Borgo Villa Certano
Siena
10.0 out of 10, Exceptional, (1 review)
"Absolutely beautiful setting out in the hills of Siena. Our apartment was clean and functional. It really needed some easy comfortable chairs to sit in. There was definitely room in the apartment."
United States
Angela
Borgo Villa Certano
A hallway leading to an outdoor patio with a table and chairs, framed artwork on the walls, and a rustic ceiling.

4. Casale di Villore

Casale di Villore
Poggibonsi
10.0 out of 10, Exceptional, (5 reviews)
"Fantastic property. Can’t wait to return next year. "
Canada
Owen
Casale di Villore
A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

5. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is RM523
RM593 total
includes taxes & fees
8 Nov - 9 Nov
Agriturismo La Ferrozzola
An outdoor swimming pool with lounge chairs and umbrellas, surrounded by stone buildings and trees.

6. Tasteful Countryside Stay

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

7. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.6 out of 10, Exceptional, (14 reviews)
"The property was perfect and the host was so nice and helpful. We would definitely stay there again."
United States
Andrew
The price is RM356
RM414 total
includes taxes & fees
2 Nov - 3 Nov
Casa Vacanze Le Case
A stone building with a tiled roof, surrounded by dry grass and trees, set in a hilly landscape.

8. Zampugna

Zampugna
Trequanda
9.2 out of 10, Wonderful, (5 reviews)
"Beautiful and host is great!"
United States
August
Zampugna
A stone pathway leading to a wooden door with a metal gate, surrounded by greenery and a small tree.

9. Chianti Classico Home Panoramic View

Chianti Classico Home Panoramic View
Castellina in Chianti
Chianti Classico Home Panoramic View
A room with a large wooden door, a rustic wooden bench, and a vase with dried plants.

10. 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 historic building with a bell tower, surrounded by lush greenery and hills.

11. Casa di Giulio

Casa di Giulio
Castiglione d'Orcia
Casa di Giulio
A covered patio area with outdoor seating, a stone floor, and a view of the garden and trees.

12. Tranquil Stay in Montepulciano

Tranquil Stay in Montepulciano
Montepulciano
Tranquil Stay in Montepulciano
An outdoor dining area with a table set for two, overlooking a vineyard.

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

14. 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 rectangular swimming pool with a brick border, surrounded by lounge chairs and umbrellas, with a building in the background.

15. 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
A poolside setting with a champagne bottle, fruit bowl, and glasses on a clear tray.

16. Cozy Holiday Home With Pool in Sienna Italy

Cozy Holiday Home With Pool in Sienna Italy
Siena
Cozy Holiday Home With Pool in Sienna Italy
An outdoor seating area with wicker furniture, a table with fruit and wine glasses, and a brick wall in the background.

17. Farmhouse in Tuscany Near Siena & Hot Springs

Farmhouse in Tuscany Near Siena & Hot Springs
Castelnuovo Berardenga
Farmhouse in Tuscany Near Siena & Hot Springs
A stone building with a tiled roof, surrounded by greenery and trees.

18. 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 building with a wooden door, potted plants, and a tiled floor.

19. Chiara House In Galenda

Chiara House In Galenda
Gaiole in Chianti
Chiara House In Galenda
A villa with a stone facade, terracotta roof tiles, and a central courtyard with a swimming pool.

20. Casa La Cedrina Pool Lornano

Casa La Cedrina Pool Lornano
Monteriggioni
Casa La Cedrina Pool Lornano
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

La Cisterna

La Cisterna

10/10 Excellent
"The service was wonderful!"
Tracy 1-night trip
Posted 10 hours ago
La Cisterna

Find out more about Province of Siena

Province of Siena Private Holiday Homes information

Number of reviews
124
Accommodation
190 Private Holiday Homes
Lowest Price
RM414
Highest Price
RM593

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