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 villa with a swimming pool, outdoor seating, and a tennis court.

1. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (81 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is S$195
includes taxes & fees
28 Oct - 29 Oct
Villa Curina Resort
A table set with breakfast items on a balcony overlooking a historic town.

2. Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (135 reviews)
"We had a great stay!"
United States
Suelina
The price is S$208
includes taxes & fees
21 Nov - 22 Nov
Residenza d'Epoca Palazzo Borghesi
A narrow hallway with a wooden bench, a radiator, and a wooden cabinet.

3. 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$163
includes taxes & fees
9 Nov - 10 Nov
Il Battistero Siena - Residenza d'Epoca
A narrow street with buildings on either side, featuring arched windows and a pedestrian walkway.

4. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (216 reviews)
"Very clean and comfortable, great location and staff"
United States
Heather
The price is S$109
includes taxes & fees
22 Nov - 23 Nov
B&B Il Corso
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.

5. 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
20 Nov - 21 Nov
Tuscasì Aparthotel
A historic building with a clock tower, arched windows, and a shop selling souvenirs.

6. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (117 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$260
includes taxes & fees
10 Nov - 11 Nov
PALAZZO DEL PAPA
A room with a white wardrobe, a glass-top table, a chair, and a large ornate mirror.

7. B&B Palazzo del Magnifico

B&B Palazzo del Magnifico
Siena City Centre
9.8 out of 10, Exceptional, (75 reviews)
"Wonderful place, great location."
United States
Khaled
The price is S$140
includes taxes & fees
15 Nov - 16 Nov
B&B Palazzo del Magnifico
A bathroom with a window view of a historic building and a tiled roof.

8. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (494 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$162
includes taxes & fees
2 Nov - 3 Nov
Siena Vip
A view through a window of a stone staircase leading to a building with arched windows and a tower, overlooking a hilly landscape.

9. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.6 out of 10, Exceptional, (103 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
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 hallway with a wooden bench, a small table with a bottle and glasses, and a door with a decorative panel.

11. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (166 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is S$212
includes taxes & fees
8 Nov - 9 Nov
Hotel San Gregorio
A courtyard with outdoor seating, a building with multiple windows, and a stone wall.

12. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (12 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is S$409
includes taxes & fees
1 Nov - 2 Nov
Palazzo Saloni
A historic building with arched windows and a prominent entrance.

13. 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$214
includes taxes & fees
23 Nov - 24 Nov
Casa Ciseri
A courtyard with a large building featuring arched windows and a tower. There is a parking lot with several cars.

14. Al Mercato B&B

Al Mercato B&B
Siena City Centre
9.0 out of 10, Wonderful, (107 reviews)
"This B and B is great. In the centre of everything."
Canada
Sandra
The price is S$108
includes taxes & fees
22 Nov - 23 Nov
Al Mercato B&B
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

15. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (59 reviews)
"We booked this last - minute and were really impressed with the whole experience. The property and grounds are beautiful. Staff was so friendly and helpful. The rooms were well appointed and quiet. Beds were too firm for our liking, but it was easy to overlook as the entire stay was really great. Good options in the restaurant too. The block of hotel rooms is in a retirement resort, which I think is a wonderful idea! Very much enjoyed our stay. We had a car and parking was free."
United States
Heidi
The price is S$186
includes taxes & fees
15 Nov - 16 Nov
Guild Living Siena Senior Resort & Residence
A stone building with a garden in front.

16. 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
27 Oct - 28 Oct
Borgo Argenina
A table with two wine glasses, a bottle, and a book.

17. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (100 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$104
includes taxes & fees
18 Nov - 19 Nov
Domus il Palio B&B
An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

18. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (186 reviews)
"Very peaceful and scenic. Wish we had stayed longer."
United States
Amir
The price is S$136
includes taxes & fees
28 Oct - 29 Oct
Bosco della Spina
A historic building with a tower, a courtyard, and a well-lit entrance.

19. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (185 reviews)
"Great Historical location."
Canada
Robert
The price is S$103
includes taxes & fees
23 Nov - 24 Nov
Abbadia Sicille Relais
A hot tub with two glasses of a beverage.

20. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is S$250
includes taxes & fees
29 Oct - 30 Oct
Villa di Sotto
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

10/10 Excellent
"Fabulous service. Gorgeous location and pristine hotel. Great food choices and services."
mauricio 2-night trip
Posted 1 hour ago
Castiglion del Bosco, A Rosewood Hotel