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 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 wine cellar with stone walls, wine racks, and tables with glasses and candles.

2. 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$192
includes taxes & fees
5 Nov - 6 Nov
Il Battistero Siena - Residenza d'Epoca
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

3. 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$213
includes taxes & fees
25 Oct - 26 Oct
Palazzo Pacini
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

4. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (55 reviews)
"Amazing! Thank you!"
United Kingdom
Lucy
The price is S$184
includes taxes & fees
9 Nov - 10 Nov
Guild Living Siena Senior Resort & Residence
A bathroom with a window view of a historic building and a tiled roof.

5. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (488 reviews)
"Great location right in the heart of everything and next to an escalator that takes you to the main plaza. Very comfortable bed, friendly staff. Convenient parking option very close by."
United States
Heather
The price is S$163
includes taxes & fees
2 Nov - 3 Nov
Siena Vip
A table set with breakfast items on a balcony overlooking a historic town.

6. Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (132 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
A villa with a swimming pool, outdoor seating, and a tennis court.

7. 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$156
includes taxes & fees
21 Oct - 22 Oct
Villa Curina Resort
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, (214 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$121
includes taxes & fees
4 Nov - 5 Nov
B&B Il Corso
A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

9. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (116 reviews)
"Hamza is so helpful!! Finding the property is a little tricky, but he helped every step of the way! He also provided excellent dining suggestions and a great cooking class!"
United States
Charles
The price is S$242
includes taxes & fees
10 Nov - 11 Nov
PALAZZO DEL PAPA
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.

10. 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$98
includes taxes & fees
4 Nov - 5 Nov
Tuscasì Aparthotel
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

11. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (161 reviews)
"Great location, clean room and communal space. We were disappointed that we were given a room with jacuzzi but no shower and refrigerator was broken. Overall a nice experience"
United States
Julia
The price is S$189
includes taxes & fees
8 Nov - 9 Nov
Hotel San Gregorio
A historic building with arched windows and a prominent entrance.

12. 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
2 Nov - 3 Nov
Casa Ciseri
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

13. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (11 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is S$366
includes taxes & fees
11 Nov - 12 Nov
Palazzo Saloni
An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

14. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (183 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$136
includes taxes & fees
1 Nov - 2 Nov
Bosco della Spina
An arched brick corridor with gravel flooring, potted plants, and a gate leading to a garden area.

15. Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (46 reviews)
"Clean room, amazing staff"
Canada
Talha
The price is S$344
includes taxes & fees
12 Oct - 13 Oct
Ca' Bianca Tuscany Relais
A narrow street with stone buildings, a tower, and an archway.

16. Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
10.0 out of 10, Exceptional, (1 review)
"Fantastic all around experience. The rooms were beautiful and clean and this unique mix of rustic modern Italian styling. Located right in the heart of the old city made it very easy to walk everywhere. The service was fantastic, I was able to message the team and within a minute I got the help and had my questions answered. I’d definitely stay there again."
Canada
Bradley
The price is S$151
includes taxes & fees
6 Nov - 7 Nov
Materia Rooms San Gimignano
A stone building with a garden in front.

17. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (28 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is S$251
includes taxes & fees
15 Oct - 16 Oct
Borgo Argenina
A room with a bed, a leather sofa, and a window with a view of a building outside.

18. 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$104
includes taxes & fees
8 Nov - 9 Nov
Al Mercato B&B
A table with two wine glasses, a bottle, and a book.

19. 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 with a courtyard, a swimming pool, and vineyard fields in the background.

20. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (42 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is S$278
includes taxes & fees
19 Oct - 20 Oct
Riserva di Fizzano Residence
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
"We stayed here for three nights and absolutely loved it. The hotel is charming, convenient and comfortable. Breakfast was very good, with a nice choice of foods, and the lounge/bar is a great place to relax. The staff were very helpful with directions and bookings. We would gladly stay here again."
Ralph 2-night trip
Posted 16 hours ago
Hotel Italia