Province of Siena Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Food and drink
Hotel San Gregorio

Residence in Pienza

Hotel San Gregorio
3.0 star property
9.4 out of 10, Exceptional, (134)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
The price is S$297
includes taxes & fees
5 Jan - 6 Jan, 2026
Hotel San Gregorio
Lobby lounge
ApartHotel Anghel

Apartment in Siena

ApartHotel Anghel
8.4 out of 10, Very good, (334)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
The price is S$107
includes taxes & fees
18 Dec - 19 Dec
ApartHotel Anghel
Terrace/patio
Abbadia Sicille Relais

Residence in Trequanda

Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is S$103
includes taxes & fees
14 Dec - 15 Dec
Abbadia Sicille Relais
Premium bedding, down duvets, pillow-top beds, minibar
Tuscasì Aparthotel

Aparthotel in Sovicille

Tuscasì Aparthotel
9.2 out of 10, Wonderful, (25)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is S$113
includes taxes & fees
20 Dec - 21 Dec
Tuscasì Aparthotel
Tasting room
Il Battistero Siena - Residenza d'Epoca

Residence in Siena City Centre

Il Battistero Siena - Residenza d'Epoca
9.6 out of 10, Exceptional, (191)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
City view
Regis Condo

Apartment in Siena City Centre

Regis Condo
9.4 out of 10, Exceptional, (65)
"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."
United States
Ben
Regis Condo
1 treatment room, massages
Casanova - Panoramic Rooms and Suites

Residence in San Quirico d'Orcia

Casanova - Panoramic Rooms and Suites
3.0 star property
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
Casanova - Panoramic Rooms and Suites
Daily continental breakfast (EUR 20 per person)
Residenza d'Epoca Palazzo Borghesi

Residence in Siena City Centre

Residenza d'Epoca Palazzo Borghesi
9.6 out of 10, Exceptional, (116)
"We enjoyed our stay here. Convenient, clean, central to city center, shops, and restaurants. We would stay here again."
United States
Linda
The price is S$275
includes taxes & fees
6 Jan - 7 Jan, 2026
Residenza d'Epoca Palazzo Borghesi
Free WiFi, bed sheets
Bellarmino Boutique Apartments

Apartment in Montepulciano

Bellarmino Boutique Apartments
6.0 out of 10, (1)
"Heat didnt work, it was FREEZING. Contact didnt seem to be local, seemed like they were managing remotely and couldnt or wouldnt send anyone to help. Nor did they really seem to care. Beautiful area though!"
United States
JON
The price is S$148
includes taxes & fees
11 Jan - 12 Jan, 2026
Bellarmino Boutique Apartments
Property entrance
Residenza Fabroni

Residence in Montepulciano

Residenza Fabroni
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is S$143
includes taxes & fees
15 Dec - 16 Dec
Residenza Fabroni
Exterior
Camping Siena Colleverde

Camping in Scacciapensieri

Camping Siena Colleverde
3.0 star property
8.2 out of 10, Very good, (159)
"Safe, great proximity to Siena without being too close, nice pool."
United States
Martha
Camping Siena Colleverde
Terrace/patio
Camping Boschetto Di Piemma

Camping in San Gimignano

Camping Boschetto Di Piemma
3.0 star property
8.8 out of 10, Excellent, (85)
"The mobile homes were a great alternative when Via Francigena hostels were full. Friendly people, swimming pool was wonderful , and an easy walk back and forth to San Gimignano."
United States
Martha
Camping Boschetto Di Piemma
Property entrance
Il Tosco

Residence in Montepulciano

Il Tosco
10.0 out of 10, Exceptional, (115)
"The staff was courteous, the food was amazing, and the location was great. We were very impressed"
United States
Joshua
The price is S$378
includes taxes & fees
15 Dec - 16 Dec
Il Tosco
Exterior detail
La Casa di Ines

Aparthotel in San Gimignano City Centre

La Casa di Ines
9.6 out of 10, Exceptional, (7)
"Love this town. Location is great "
United States
William
The price is S$118
includes taxes & fees
22 Dec - 23 Dec
La Casa di Ines
Balcony
Osteria del Borgo

Residence in Montepulciano

Osteria del Borgo
9.0 out of 10, Wonderful, (156)
"Staff and location were both excellent."
United States
Nicholas
Osteria del Borgo
Interior detail
La Coroncina Lodging

Aparthotel in Siena

La Coroncina Lodging
10.0 out of 10, Exceptional, (42)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is S$128
includes taxes & fees
14 Dec - 15 Dec
La Coroncina Lodging
24-inch flat-screen TV with digital channels, TV
Palazzo Lenzi

Apartment in Siena City Centre

Palazzo Lenzi
9.0 out of 10, Wonderful, (2)
"Very very nice. Enjoyed our stay. Air conditioning did not work well so a bit hot. But overall very nice. "
United States
Daniel
The price is S$335
includes taxes & fees
15 Dec - 16 Dec
Palazzo Lenzi
Premium bedding, Select Comfort beds, minibar, in-room safe
La Terrazza Sul Campo Rooming House

Residence in Siena City Centre

La Terrazza Sul Campo Rooming House
9.8 out of 10, Exceptional, (239)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House
Front of property
Casa Ciseri

Apartment in Siena City Centre

Casa Ciseri
9.8 out of 10, Exceptional, (9)
"Very nice stay!"
United States
Danielle
The price is S$368
includes taxes & fees
14 Dec - 15 Dec
Casa Ciseri
Exterior
Borgo Argenina

Aparthotel in Gaiole in Chianti

Borgo Argenina
9.8 out of 10, Exceptional, (22)
"A planned Tuscany trip in the making for over a year. Saw this property came up while doing research and had a wonderful and romantic history. The property was even more beautiful than the pictures posted. It definitely caters to all types of travellers. A perfect bed and breakfast stay. Definitely recommend and will be back again. "
Canada
Nancy
Borgo Argenina
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

Villa del Sole Siena

Villa del Sole Siena

10/10 Excellent
"Amazing rooms and service!!"
Janet 1-night trip
Posted 4 days ago
Villa del Sole Siena