Province of Siena Holiday Rentals

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Our top choices for Province of Siena holiday rentals

Breakfast, lunch, dinner served; local cuisine
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 HK$1,575
HK$1,788 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel San Gregorio
View from room
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 HK$515
HK$685 total
includes taxes & fees
21 Dec - 22 Dec
Tuscasì Aparthotel
Lobby lounge
ApartHotel Anghel

Apartment in Siena

ApartHotel Anghel
8.4 out of 10, Very good, (335)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
The price is HK$548
HK$639 total
includes taxes & fees
19 Dec - 20 Dec
ApartHotel Anghel
View from room
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 HK$589
HK$676 total
includes taxes & fees
19 Dec - 20 Dec
Abbadia Sicille Relais
Bar (on property)
Il Battistero Siena - Residenza d'Epoca

Residence in Siena City Centre

Il Battistero Siena - Residenza d'Epoca
9.6 out of 10, Exceptional, (193)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
Exterior
Farmhouse in the heart of the real chiantishire

Holiday Home in Castellina in Chianti

Farmhouse in the heart of the real chiantishire
10.0 out of 10, Exceptional, (148)
"Very relaxing farmhouse cottage with pleasant and peaceful views .The only drawback is the ruddy gravel access road which makes for an unpleasant excursion to and from the property."
United States
William H.
Farmhouse in the heart of the real chiantishire
Pool
Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Villa in Siena

Private and cozy retreat in Montalcino with private pool surrounded by vineyards
9.4 out of 10, Exceptional, (67)
"Just perfect. Hostess was very responsive before and during my trip with any questions I had. The property was immaculate and I will definitely be staying again. When you think of a Tuscan villa, this is exactly what it should be. "
United States
Andrew G.
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Front of property – evening/night
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
The price is HK$1,795
HK$2,011 total
includes taxes & fees
26 Dec - 27 Dec
Casanova - Panoramic Rooms and Suites
Private kitchen
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
View from room
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 HK$1,405
HK$1,583 total
includes taxes & fees
6 Jan - 7 Jan 2026
Residenza d'Epoca Palazzo Borghesi
Exterior detail
The House of Alice, charm and relaxation

Holiday Home in Montalcino (SI)

The House of Alice, charm and relaxation
9.8 out of 10, Exceptional, (67)
"Really enjoyed our stay. Loved the town and the accommodation was superb. "
Australia
Michelle C.
The price is HK$1,370
HK$1,854 total
includes taxes & fees
11 Jan - 12 Jan 2026
The House of Alice, charm and relaxation
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
Outdoor dining
Villa with large garden in the Chianti hills

Holiday Home in Siena

Villa with large garden in the Chianti hills
9.6 out of 10, Exceptional, (75)
"Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany."
United States
Jessica P.
Villa with large garden in the Chianti hills
Lobby
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 HK$681
HK$786 total
includes taxes & fees
13 Jan - 14 Jan 2026
Residenza Fabroni
Outdoor dining
san gimignano apartment in historical center, courtyard and fast free wifi

Apartment in San Gimignano City Centre

san gimignano apartment in historical center, courtyard and fast free wifi
9.6 out of 10, Exceptional, (36)
"Great experience in a medieval villa converted to apartments. We were there for one night and enjoyed it very much!"
United States
Matthew E.
The price is HK$822
HK$1,306 total
includes taxes & fees
6 Jan - 7 Jan 2026
san gimignano apartment in historical center, courtyard and fast free wifi
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 HK$673
HK$786 total
includes taxes & fees
19 Dec - 20 Dec
La Casa di Ines
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 HK$699
HK$805 total
includes taxes & fees
11 Jan - 12 Jan 2026
Bellarmino Boutique Apartments
Outdoor pool
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

Villa in San Gimignano

San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
10.0 out of 10, Exceptional, (107)
"Great villa in a lovely location. We (8 adults and 2 children) really enjoyed our trip. It had everything we needed and a beautiful view from the pool! Thank you to Allesandro for helping us book things in the local area too. "
United Kingdom
Catherine T.
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
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 HK$1,774
HK$1,988 total
includes taxes & fees
22 Dec - 23 Dec
Il Tosco
Outdoor dining
Hilltop house in the heart of Tuscany with private pool

Villa in Montisi

Hilltop house in the heart of Tuscany with private pool
9.8 out of 10, Exceptional, (94)
"Lovely home with spectacular views! The home greatly exceeded our expectations. It had everything we needed for our 6 day. When not our touring the charming small Tuscany towns, we enjoyed the peace and quiet of the back porch and pool area. We kept the windows open and enjoyed the sweet breezes blowing through. If you're looking the perfect home to rent in Tuscany, this is the one. "
United States
Teresa G.
Hilltop house in the heart of Tuscany with private pool
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 Certosa Di Maggiano

Hotel Certosa Di Maggiano

10/10 Excellent
"The best in Siena."
David 1-night trip
Posted 5 days ago
Hotel Certosa Di Maggiano