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

Province of Siena Holiday Rentals

  • 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

Our top choices for Province of Siena holiday rentals

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.

1. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (32 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
4 Nov - 5 Nov
Tuscasì Aparthotel
A bakery display with pastries and a coffee station.

2. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (215 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$110
includes taxes & fees
2 Nov - 3 Nov
B&B Il Corso
A villa with a swimming pool, outdoor seating, and a tennis court.

3. 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$171
includes taxes & fees
22 Oct - 23 Oct
Villa Curina Resort
An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

4. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (185 reviews)
"Very peaceful and scenic. Wish we had stayed longer."
United States
Amir
The price is S$137
includes taxes & fees
26 Oct - 27 Oct
Bosco della Spina
An interior with stone walls, wooden doors, and a bar area with stools and bottles.

5. Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (67 reviews)
"I loved the stay here. A great quiet place with an awesome restaurant and unbelievable staff. "
United States
Louie
The price is S$271
includes taxes & fees
19 Oct - 20 Oct
Borgo Il Poggiaccio
A historic building with a tower, a courtyard, and a well-lit entrance.

6. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (184 reviews)
"Great Historical location."
Canada
Robert
The price is S$119
includes taxes & fees
17 Nov - 18 Nov
Abbadia Sicille Relais
A stone courtyard with a bench, potted plants, and a building in the background.

7. Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.6 out of 10, Exceptional, (27 reviews)
"A wonderful stay. "
United States
Sally
The price is S$130
includes taxes & fees
17 Nov - 18 Nov
Casa di Campagna in Toscana
A patio area with outdoor seating, potted plants, and a view of the landscape.

8. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (73 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is S$177
includes taxes & fees
19 Oct - 20 Oct
Affitacamere Maria Gabriella
A bathroom with a window view of a historic building and a tiled roof.

9. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (491 reviews)
"Very friendly staff and great location close to the center of town. Breakfast was a nice touch and just what we needed to start the day. Would recommend!"
United States
Jacob
The price is S$158
includes taxes & fees
12 Nov - 13 Nov
Siena Vip
A spacious hotel room with a large bed, a sitting area with chairs, and a view through an arched doorway to another room.

10. La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (254 reviews)
"Great stay. Thanks for the hospitality and kindness."
United Kingdom
Agnieszka
The price is S$187
includes taxes & fees
2 Nov - 3 Nov
La Terrazza Sul Campo Rooming House
A wine cellar with stone walls, wine racks, and tables with glasses and candles.

11. Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (222 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$178
includes taxes & fees
12 Nov - 13 Nov
Il Battistero Siena - Residenza d'Epoca
A room with a bed, a leather sofa, and a window with a view of a building outside.

12. Al Mercato B&B

Al Mercato B&B
Siena City Centre
9.0 out of 10, Wonderful, (105 reviews)
"Great location."
Canada
Marie-Christine
The price is S$121
includes taxes & fees
16 Nov - 17 Nov
Al Mercato B&B
A table with two wine glasses, a bottle, and a book.

13. 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
25 Oct - 26 Oct
Domus il Palio B&B
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

14. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is S$236
includes taxes & fees
21 Oct - 22 Oct
Villa di Sotto
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

15. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (163 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is S$190
includes taxes & fees
8 Nov - 9 Nov
Hotel San Gregorio
A table set with breakfast items on a balcony overlooking a historic town.

16. Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (133 reviews)
"We had a great experience Property is perfectly located."
United States
Roman
The price is S$206
includes taxes & fees
9 Nov - 10 Nov
Residenza d'Epoca Palazzo Borghesi
A terrace with a table set for dining, overlooking a scenic landscape with a castle in the distance.

17. FonteLiving

FonteLiving
San Casciano dei Bagni
10.0 out of 10, Exceptional, (20 reviews)
"Fabulous apt., elegant, clean lines, quiet, pool and wonderful staff"
Italy
Dauray
The price is S$118
includes taxes & fees
23 Oct - 24 Oct
FonteLiving
A staircase with a wooden handrail, a potted plant, and a chair in a hallway.

18. Villa Fontis Rapolano

Villa Fontis Rapolano
Rapolano Terme
10.0 out of 10, Exceptional, (1 review)
"Bella struttura, nuova, pulita in posizione comoda"
Italy
Barbara
The price is S$127
includes taxes & fees
22 Oct - 23 Oct
Villa Fontis Rapolano
A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

19. Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.8 out of 10, Exceptional, (20 reviews)
"The unit is very clean, awesome breakfast, beautiful view"
Canada
Ivan
The price is S$167
includes taxes & fees
8 Nov - 9 Nov
Corte Francigena - Apartments
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

20. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (355 reviews)
"Humming noise in the room. Slow internet. Fine bed. Good location."
Netherlands
Lauro
The price is S$94
includes taxes & fees
3 Nov - 4 Nov
ApartHotel Anghel
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

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"We had the most amazing stay in this beautiful hotel. Our room was so charming, and the entire hotel felt warm and welcoming in the most Italian way. Breakfast each morning included a beautiful spread of savory and sweet, and croissants that were better than Paris. The terrace sunsets looking over Siena welcomed us each evening after a long day of walking. Location was top notch. Our only “complaint” was that the bed was VERY firm. We will be back!!"
susan 7-night trip
Posted 7 hours ago
Palazzo Ravizza