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, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is S$168
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.

2. 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$125
includes taxes & fees
27 Oct - 28 Oct
Bosco della Spina
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.

3. 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 stone courtyard with a bench, potted plants, and a building in the background.

4. 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$143
includes taxes & fees
30 Oct - 31 Oct
Casa di Campagna in Toscana
A bakery display with pastries and a coffee station.

5. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (213 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 terrace with a table set for dining, overlooking a scenic landscape with a castle in the distance.

6. 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$105
includes taxes & fees
4 Nov - 5 Nov
FonteLiving
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

7. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (354 reviews)
"Humming noise in the room. Slow internet. Fine bed. Good location."
Netherlands
Lauro
The price is S$94
includes taxes & fees
8 Nov - 9 Nov
ApartHotel Anghel
A table with two wine glasses, a bottle, and a book.

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

9. 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
4 Nov - 5 Nov
La Terrazza Sul Campo Rooming House
An interior with stone walls, wooden doors, and a bar area with stools and bottles.

10. 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$264
includes taxes & fees
18 Oct - 19 Oct
Borgo Il Poggiaccio
A bathroom with a window view of a historic building and a tiled roof.

11. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (486 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$156
includes taxes & fees
21 Oct - 22 Oct
Siena Vip
Outdoor pool

12. Residence Arianna

Residence Arianna
Sovicille
9.6 out of 10, Exceptional, (9 reviews)
"The place is excellent! The owner and her daughter extremely friendly and kind! They helped us with everything we needed. I will definitely stay here again. I highly recommend this place!"
United States
Violeta
The price is S$198
includes taxes & fees
17 Oct - 18 Oct
Residence Arianna
A historic building with a tower, a courtyard, and a well-lit entrance.

13. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (183 reviews)
"Great Historical location."
Canada
Robert
The price is S$148
includes taxes & fees
8 Nov - 9 Nov
Abbadia Sicille Relais
A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

14. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (118 reviews)
"Felt like home. The central kitchen / coffee area felt like home."
United States
Bradley
The price is S$133
includes taxes & fees
27 Oct - 28 Oct
Idolina Guest House
A room with a bed, a leather sofa, and a window with a view of a building outside.

15. 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$106
includes taxes & fees
8 Nov - 9 Nov
Al Mercato B&B
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

16. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (160 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is S$191
includes taxes & fees
8 Nov - 9 Nov
Hotel San Gregorio
A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

17. Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.8 out of 10, Exceptional, (19 reviews)
"The unit is very clean, awesome breakfast, beautiful view"
Canada
Ivan
The price is S$170
includes taxes & fees
8 Nov - 9 Nov
Corte Francigena - Apartments
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

18. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (54 reviews)
"Amazing! Thank you!"
United Kingdom
Lucy
The price is S$202
includes taxes & fees
1 Nov - 2 Nov
Guild Living Siena Senior Resort & Residence
A staircase with a wooden handrail, a potted plant, and a chair in a hallway.

19. 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$128
includes taxes & fees
18 Oct - 19 Oct
Villa Fontis Rapolano
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

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$237
includes taxes & fees
21 Oct - 22 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

Fattoria di Vegi

Fattoria di Vegi

10/10 Excellent
"LOVE LOVE LOVE This was the highlight of our 2.5 week Toscana trip!! You won't regret booking. The space is stunning and newly opened and staff are welcoming and wonderful!"
Lauren 1-night trip
Posted 17 hours ago
Fattoria di Vegi