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

Holiday Rentals in Province of Siena

  • 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

Top Cities in Province of Siena

A historic town with tightly packed buildings, a prominent tower, and a church.
Holiday RentalsHoliday Rentals

Siena

Siena

Our top choices for Province of Siena holiday rentals

Exterior

1. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (139 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is €123
includes taxes & fees
9 Aug - 10 Aug
Bed & Breakfast Vicolo dell'Oste
Food court

2. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (146 reviews)
"Lucca was the perfect host, very accommodating to any queries we had and was always willing to help during our stay Couldn’t recommend staying here highly enough - we had a great time staying here and would highly recommend if you are in the area definitely book here"
United Kingdom
Jonathan
The price is €139
includes taxes & fees
27 Aug - 28 Aug
La Locanda di San Francesco
Interior

3. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (115 reviews)
"It was very well located ."
Canada
Marlenne
The price is €161
includes taxes & fees
11 Aug - 12 Aug
Meublé Il Riccio
Food and drink

4. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (152 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is €226
includes taxes & fees
25 Aug - 26 Aug
Hotel San Gregorio
Property entrance

5. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (130 reviews)
"Beautiful hotel in the best location. We so enjoyed our stay, especially the amazing breakfast and sweets they had available all day long."
United States
Margaret
The price is €276
includes taxes & fees
9 Aug - 10 Aug
Il Tosco
Terrace/patio

6. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (100 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is €110
includes taxes & fees
2 Sept - 3 Sept
Palazzo Pacini
Romantic Double Room, 1 Bedroom, Non Smoking | View from room

7. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (64 reviews)
"In the center of town overlooking a plaza (other rooms overlook the valley). Multiple museums, and dining and shopping options within very easy walking distance. The town and surroundings are beautiful."
United States
Harold
The price is €139
includes taxes & fees
10 Aug - 11 Aug
B&B Palazzo Tortoli
Suite Aria | Terrace/patio

8. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (39 reviews)
"Time transported to the Renaissance at this beautiful, well-kept palazzo… Riccardo’s family did a truly amazing job restoring this place and the facilities are modern & without any discomfort."
American Samoa
Melissa Hyun Joo
The price is €173
includes taxes & fees
10 Aug - 11 Aug
Delcorto Suites
Terrace/patio

9. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (178 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is €159
includes taxes & fees
9 Aug - 10 Aug
Abbadia Sicille Relais
Standard Double Room (La Piazza)

10. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (99 reviews)
"Great location, nice room, and great host!"
United States
Chris
The price is €146
includes taxes & fees
9 Aug - 10 Aug
B&B Le Scalette di Piazza
Exterior

11. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (117 reviews)
"This is a wonderful B&B that is part of the historic district. Sloping uneven floors, which is the charm of having the chance to stay in a piece of history. A very comfortable room, with breakfast at a cafe nearby. Parking option is nearby, just talk with your host who is so helpful. Wonderful location to walk and enjoy all the town has to offer."
United States
Sophie
The price is €95
includes taxes & fees
18 Aug - 19 Aug
Idolina Guest House
Aerial view

12. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (176 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 €152
includes taxes & fees
8 Sept - 9 Sept
Bosco della Spina
Premium bedding, down duvets, pillow-top beds, desk

13. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (29 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is €91
includes taxes & fees
11 Aug - 12 Aug
Tuscasì Aparthotel
Front of property

14. Podere La Chiusella

Podere La Chiusella
Rapolano Terme
9.4 out of 10, Exceptional, (32 reviews)
"Merci à Michele pour son accueil et la qualité de son hébergement. Tout était parfait. Localisation parfaite pour les Crete Sienese et Val d’Orcia. Très recommandé pour les familles. Nous reviendrons au Pozzo avec grand plaisir."
France
François
The price is €108
includes taxes & fees
7 Sept - 8 Sept
Podere La Chiusella
Property entrance

15. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (104 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is €78
includes taxes & fees
18 Aug - 19 Aug
Residenza Fabroni
Lounge

16. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (17 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
The price is €97
includes taxes & fees
9 Aug - 10 Aug
Mariani Bed & Breakfast
Suite Bernardo, Panoramica al terzo piano senza ascensore | Terrace/patio

17. PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (5 reviews)
"Clean room with friendly and helpful staff. Thank you so much for the wonderful stay"
United States
Pearlyn
The price is €114
includes taxes & fees
25 Aug - 26 Aug
PienzaLettings Suites
Balcony

18. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (110 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is €133
includes taxes & fees
9 Aug - 10 Aug
Palazzo al Torrione 2
Porch

19. Donna Nobile

Donna Nobile
San Gimignano City Centre
8.2 out of 10, Very good, (166 reviews)
"Very easy checkin, friendly staff. Loved the kitchen area!"
Canada
Treena
The price is €85
includes taxes & fees
9 Aug - 10 Aug
Donna Nobile
1 treatment room, massages

20. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (93 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
The price is €180
includes taxes & fees
31 Aug - 1 Sept
Casanova - Panoramic Rooms and Suites
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
"Two things that really made our stay at the Palazzo Ravizza exceptional were the charming terrace with a view of the Tuscan countryside, and the included continental breakfast offered in the morning, including plenty of drip coffee! ☕️ Our room was also undeniably European, with a painted ceiling and rustic furniture. The AC was sufficient, considering the daytime high on our visit was 100°. Service from the staff was very helpful, and they even called a taxi for us. The shower was hot with strong water pressure. The architecture of the hotel had some historic charm as well, with leaded glass doors, black and white marble floors, and vaulted ceilings in the public spaces. But that terrace... 😍"
Chris 1-night trip
Posted 13 hours ago
Palazzo Ravizza

Find out more about Province of Siena

Holiday Homes in Province of Siena

Search for holiday homes in Province of Siena on Expedia.ie! You can easily find your home rentals, villas, holiday apartments in Province of Siena using one of the methods below: 

  • View our selection of featured holiday homes in Province of Siena
  • Use the map to find apartments and other holiday rentals in the Province of Siena neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday homes in Province of Siena while they last

Look no further and take a look at our great range of rental properties in Province of Siena!

Explore a world of travel with Expedia