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

Province of Siena Holiday Rentals

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Our top choices for Province of Siena holiday rentals

A spacious hotel room with a large bed, a sitting area with chairs, and a view through an arched doorway to another room.

1. La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (251 reviews)
"Great stay. Thanks for the hospitality and kindness."
United Kingdom
Agnieszka
The price is S$147
includes taxes & fees
2 Nov - 3 Nov
La Terrazza Sul Campo Rooming House
A bathroom with a window view of a historic building and a tiled roof.

2. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (484 reviews)
"Fantastic location and very friendly staff, we will definitely be back"
United Kingdom
Luis
The price is S$137
includes taxes & fees
2 Nov - 3 Nov
Siena Vip
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

3. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (52 reviews)
"Amazing! Thank you!"
United Kingdom
Lucy
The price is S$170
includes taxes & fees
1 Nov - 2 Nov
Guild Living Siena Senior Resort & Residence
A table set with breakfast items on a balcony overlooking a historic town.

4. Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (131 reviews)
"We had a great experience Property is perfectly located."
United States
Roman
The price is S$217
includes taxes & fees
4 Nov - 5 Nov
Residenza d'Epoca Palazzo Borghesi
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

5. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (102 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is S$214
includes taxes & fees
6 Oct - 7 Oct
Palazzo Pacini
A villa with a swimming pool, outdoor seating, and a tennis court.

6. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is S$169
includes taxes & fees
10 Oct - 11 Oct
Villa Curina Resort
A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

7. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (114 reviews)
"The setup was more like a guest house/Bed and Breakfast. It was impeccably clean and newly renovated, which made it very cozy and comfortable. Everything needed was provided. The location was half a block from the Piazza del Campo. And last but not least, Hamza was one of the most welcoming and gracious hosts imaginable, directing us to a magical Trattoria, Pappei’s, that felt like you were visiting your own Nonna! Wonderful!!!"
United States
Walter
The price is S$261
includes taxes & fees
3 Nov - 4 Nov
PALAZZO DEL PAPA
A bakery display with pastries and a coffee station.

8. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (212 reviews)
"We enjoyed our stay very much. Staff was very friendly and offered great advise on places to eat. The rooms had great charm to them. We were delighted with our selection of where to stay."
United States
Enrique
The price is S$126
includes taxes & fees
5 Nov - 6 Nov
B&B Il Corso
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

9. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (158 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is S$210
includes taxes & fees
28 Oct - 29 Oct
Hotel San Gregorio
A wine cellar with stone walls, wine racks, and tables with glasses and candles.

10. Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (221 reviews)
"The room was so unique and convenient for everything we wanted to do. Wish we could have spent more than one night!"
United States
Kellie
The price is S$192
includes taxes & fees
5 Nov - 6 Nov
Il Battistero Siena - Residenza d'Epoca
A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

11. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (31 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is S$106
includes taxes & fees
2 Nov - 3 Nov
Tuscasì Aparthotel
A table with two wine glasses, a bottle, and a book.

12. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (99 reviews)
"Place was great, beautiful, modern, well maintained and staff was very helpful. I didn’t like that it is far from everything, far from train station, not too many options for food in the vicinity."
United States
Waleska
The price is S$99
includes taxes & fees
20 Oct - 21 Oct
Domus il Palio B&B
A stone building complex with multiple structures, surrounded by lush green fields and trees, under a partly cloudy sky.

13. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (40 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is S$260
includes taxes & fees
6 Oct - 7 Oct
Riserva di Fizzano Residence
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

14. Palazzo Saloni

Palazzo Saloni
Montalcino
9.8 out of 10, Exceptional, (9 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is S$332
includes taxes & fees
5 Nov - 6 Nov
Palazzo Saloni
A multi-story building with green shutters on windows and balconies.

15. Palazzo Masi

Palazzo Masi
Siena City Centre
9.0 out of 10, Wonderful, (88 reviews)
"Modern and useful."
United States
Macarena
The price is S$147
includes taxes & fees
27 Oct - 28 Oct
Palazzo Masi
An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

16. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (178 reviews)
"Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing. "
United Kingdom
Lizl
The price is S$125
includes taxes & fees
27 Oct - 28 Oct
Bosco della Spina
A stone building with a garden in front.

17. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (27 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is S$415
includes taxes & fees
7 Oct - 8 Oct
Borgo Argenina
A poolside area with two glasses of water, candles, and a stone pathway.

18. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (99 reviews)
"Great location and lovely pool. Rooms were large but the place is definitely dated. Breakfast was decent with a lot of options. Parking wasn’t all that great but nevertheless on the property itself"
Canada
Sunil
The price is S$242
includes taxes & fees
30 Oct - 31 Oct
Casanova - Panoramic Rooms and Suites
A historic building with arched windows and a prominent entrance.

19. Casa Ciseri

Casa Ciseri
Siena City Centre
10.0 out of 10, Exceptional, (13 reviews)
"The property is beautiful and location excellent"
United States
Tania
The price is S$230
includes taxes & fees
3 Nov - 4 Nov
Casa Ciseri
A room with a bed, a leather sofa, and a window with a view of a building outside.

20. Al Mercato B&B

Al Mercato B&B
Siena City Centre
9.0 out of 10, Wonderful, (104 reviews)
"Great location."
Canada
Marie-Christine
The price is S$118
includes taxes & fees
2 Nov - 3 Nov
Al Mercato B&B
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

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

8/10 Good
"Although the property and the staff were great, our room was a bit of a disappointment. Junior Sweet was just a giant room with furniture that was uncomfortable to use. In general the room needs an update. Not exactly what we expected. We unfortunately had a neighbor who opened up the gate outside in between our terrace which should have never happen if it had been locked. He did that because he said my husbands iPad was too loud when in fact, his was too loud and my husband who had headphones on could not hear his show so took them off so he could hear it. Needless to say we avoided our terrace after that. Shout out to Chiara and Samantha who took a desert request seriously and made two of my evenings! Michael and David’s were also wonderful!"
Ellen 5-night trip
Posted 5 hours ago
Castiglion del Bosco, A Rosewood Hotel