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 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
20 Nov - 21 Nov
Tuscasì Aparthotel
An interior with stone walls, wooden doors, and a bar area with stools and bottles.

2. 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
Borgo Il Poggiaccio
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, (81 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is S$199
includes taxes & fees
28 Oct - 29 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, (187 reviews)
"Very peaceful and scenic. Wish we had stayed longer."
United States
Amir
The price is S$136
includes taxes & fees
1 Nov - 2 Nov
Bosco della Spina
A stone courtyard with a bench, potted plants, and a building in the background.

5. 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$135
includes taxes & fees
15 Nov - 16 Nov
Casa di Campagna in Toscana
A table with two wine glasses, a bottle, and a book.

6. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (100 reviews)
"Very nice place. Nice people, clean and just nice"
Denmark
Leo
The price is S$104
includes taxes & fees
18 Nov - 19 Nov
Domus il Palio B&B
A covered corridor with brick columns, potted plants, and a view of a lush landscape.

7. 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$90
includes taxes & fees
26 Nov - 27 Nov
Abbadia Sicille Relais
A wine cellar with stone walls, wine racks, and tables with glasses and candles.

8. 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 bakery display with pastries and a coffee station.

9. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (217 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 pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

10. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is S$237
includes taxes & fees
30 Oct - 31 Oct
Villa di Sotto
A patio area with outdoor seating, potted plants, and a view of the landscape.

11. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (74 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is S$176
includes taxes & fees
28 Oct - 29 Oct
Affitacamere Maria Gabriella
A terrace with a table set for dining, overlooking a scenic landscape with a castle in the distance.

12. FonteLiving

FonteLiving
San Casciano dei Bagni
10.0 out of 10, Exceptional, (21 reviews)
"Fabulous apt., elegant, clean lines, quiet, pool and wonderful staff"
Italy
Dauray
The price is S$111
includes taxes & fees
29 Oct - 30 Oct
FonteLiving
A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

13. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (118 reviews)
"A truly special place!"
United States
Jaiden
The price is S$127
includes taxes & fees
25 Nov - 26 Nov
Idolina Guest House
A table set with breakfast items on a balcony overlooking a historic town.

14. 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
4 Nov - 5 Nov
Residenza d'Epoca Palazzo Borghesi
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

15. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (355 reviews)
"Great stay highly recommend!!"
United States
jon
The price is S$87
includes taxes & fees
15 Nov - 16 Nov
ApartHotel Anghel
A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

16. 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
7 Nov - 8 Nov
PALAZZO DEL PAPA
A room with a white wardrobe, a glass-top table, a chair, and a large ornate mirror.

17. B&B Palazzo del Magnifico

B&B Palazzo del Magnifico
Siena City Centre
9.8 out of 10, Exceptional, (76 reviews)
"Wonderful place, great location."
United States
Khaled
The price is S$145
includes taxes & fees
8 Nov - 9 Nov
B&B Palazzo del Magnifico
A bathroom with a window view of a historic building and a tiled roof.

18. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (495 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$147
includes taxes & fees
2 Nov - 3 Nov
Siena Vip
A room with a bed, a leather sofa, and a window with a view of a building outside.

19. 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
15 Nov - 16 Nov
Al Mercato B&B
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

20. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (167 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
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

Hotel Borgo San Luigi

Hotel Borgo San Luigi

10/10 Excellent
"Borgo San Luis is a luxury destination! The four of us were treated as honored guests of great renown. The grounds were wide, varied, and immaculate. The breakfasts were special events for us foodies, and the swimming pool was refreshing even in October!. Parking was free, secure, and accessible. We easily saw why the Borgo was a destination for the weddings, feasts, and meetings that were taking place at the time of our visit -- but they were never intrusive. The staff were multi-lingual and honestly could not do enough for us. Should you ever desire a dream from which that you did not want to awaken, visit Borgo San Luis."
John 2-night trip
Posted 14 hours ago
Hotel Borgo San Luigi