Search Holiday Rentals in Province of Siena

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

Top Holiday Rentals in Province of Siena

Breakfast, lunch, dinner served; local cuisine
Hotel San Gregorio

Hotel San Gregorio

3.0 star property
Pienza
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 ฿6,533
฿7,410 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel San Gregorio
Lobby lounge
ApartHotel Anghel

ApartHotel Anghel

Siena
8.4 out of 10, Very good, (334)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
The price is ฿2,210
฿2,580 total
includes taxes & fees
10 Dec - 11 Dec
ApartHotel Anghel
View from room
Abbadia Sicille Relais

Abbadia Sicille Relais

4.0 star property
Trequanda
8.8 out of 10, Excellent, (165)
"We stayed there for 1 night our our way to Rome. BEAUTIFUL. Bed was very comfortable as well. 10/10 will recommend to everyone "
United States
Brittnay
The price is ฿2,553
฿2,920 total
includes taxes & fees
10 Dec - 11 Dec
Abbadia Sicille Relais
Royal Apartment | View from room
Tuscasì Aparthotel

Tuscasì Aparthotel

Sovicille
9.0 out of 10, Wonderful, (24)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is ฿2,241
฿2,576 total
includes taxes & fees
8 Dec - 9 Dec
Tuscasì Aparthotel
Bar (on property)
Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca

Siena City Centre
9.6 out of 10, Exceptional, (191)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
Grand Apartment with Garden | Private kitchen | Full-sized fridge, microwave, oven, stovetop
Regis Condo

Regis Condo

Siena City Centre
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
Front of property – evening/night
Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites

3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
The price is ฿6,012
฿6,762 total
includes taxes & fees
11 Dec - 12 Dec
Casanova - Panoramic Rooms and Suites
Panoramic Suite, City View | View from room
Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi

Siena City Centre
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 ฿6,215
฿6,985 total
includes taxes & fees
5 Jan - 6 Jan 2026
Residenza d'Epoca Palazzo Borghesi
Deluxe Apartment, 2 Bedrooms, Balcony | Free WiFi, bed sheets
Bellarmino Boutique Apartments

Bellarmino Boutique Apartments

Montepulciano
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 ฿3,396
฿3,884 total
includes taxes & fees
9 Dec - 10 Dec
Bellarmino Boutique Apartments
Lobby
Residenza Fabroni

Residenza Fabroni

Montepulciano
8.8 out of 10, Excellent, (93)
"We had a great stay! Beautiful on the roof top terrace!"
United States
Jennifer
The price is ฿2,677
฿3,093 total
includes taxes & fees
9 Dec - 10 Dec
Residenza Fabroni
Exterior
Camping Siena Colleverde

Camping Siena Colleverde

3.0 star property
Scacciapensieri
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
2 bars/lounges
Camping Boschetto Di Piemma

Camping Boschetto Di Piemma

3.0 star property
San Gimignano
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

Il Tosco

Montepulciano
10.0 out of 10, Exceptional, (114)
"The staff was courteous, the food was amazing, and the location was great. We were very impressed"
United States
Joshua
The price is ฿8,390
฿9,377 total
includes taxes & fees
8 Dec - 9 Dec
Il Tosco
Exterior detail
La Casa di Ines

La Casa di Ines

San Gimignano City Centre
9.6 out of 10, Exceptional, (7)
"Love this town. Location is great "
United States
William
The price is ฿2,462
฿2,894 total
includes taxes & fees
19 Dec - 20 Dec
La Casa di Ines
Suite | Premium bedding, Select Comfort beds, minibar, in-room safe
La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House

Siena City Centre
9.8 out of 10, Exceptional, (239)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House
Standard Room | Exterior
Osteria del Borgo

Osteria del Borgo

Montepulciano
9.0 out of 10, Wonderful, (156)
"Staff and location were both excellent."
United States
Nicholas
Osteria del Borgo
Daily cooked-to-order breakfast (EUR 15 per person)
La Coroncina Lodging

La Coroncina Lodging

Siena
10.0 out of 10, Exceptional, (42)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is ฿2,800
฿3,228 total
includes taxes & fees
10 Dec - 11 Dec
La Coroncina Lodging
Deluxe Apartment, City View | Living area | 24-inch flat-screen TV with digital channels, TV
Palazzo Lenzi

Palazzo Lenzi

Siena City Centre
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 ฿7,346
฿8,229 total
includes taxes & fees
10 Dec - 11 Dec
Palazzo Lenzi
Deluxe Apartment | Living area | 50-inch Smart TV with cable channels
Casa Ciseri

Casa Ciseri

Siena City Centre
9.8 out of 10, Exceptional, (9)
"Beautiful property in the center of Siena! "
United States
Maura
The price is ฿8,083
฿9,040 total
includes taxes & fees
15 Dec - 16 Dec
Casa Ciseri
Property entrance
Palazzo Pacini

Palazzo Pacini

Colle di Val d'Elsa
9.8 out of 10, Exceptional, (98)
"Such a beautiful gem of a hotel. Steeped in Florentine style. Comfortable and classy. Definitely would recommend "
United States
George
Palazzo Pacini
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

Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

10/10 Excellent
"Everything was perfect. Warm welcome, comfortable and spacious rooms, great breakfast. The staff was very kind and friendly. I also recommend the wine tasting experience. Highly recommended!"
Pedro 1-night trip
Posted 2 days ago
Relais Villa Grazianella - UNA Esperienze

Find out more about Province of Siena

Vacation Apartments in Province of Siena

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

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