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 Cities in Province of Siena

Holiday RentalsHoliday Rentals

Siena

Siena

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 €196
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 €66
includes taxes & fees
14 Dec - 15 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 €71
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 €75
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
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)
"What a lovely place, I will recommend this fabulous home to friends and family and will be returning sometime soon."
United Kingdom
peter H.
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
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
The price is €220
includes taxes & fees
26 Dec - 27 Dec
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 €184
includes taxes & fees
6 Jan - 7 Jan 2026
Residenza d'Epoca Palazzo Borghesi
Deluxe Apartment, 2 Bedrooms, Balcony
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 €98
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 €94
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
Property grounds
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
Superior Mobile Home | 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
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, (106)
"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 €252
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 €78
includes taxes & fees
20 Dec - 21 Dec
La Casa di Ines
Exterior
Villa in Montalcino, exclusive for you, stunning view!!!

Villa in Montalcino

Villa in Montalcino, exclusive for you, stunning view!!!
10.0 out of 10, Exceptional, (86)
"Lovely villa in a beautiful location. "
United Kingdom
helen S.
Villa in Montalcino, exclusive for you, stunning view!!!
Pool
panoramica casa con piscina privata

Villa in siena

panoramica casa con piscina privata
7.0 out of 10, Good, (10)
"We had a lovely stay and the hosts were warm, accommodating and responsive. The location is incredible -- extensive views from both sides of the property; the hilltop village setting is out of a postcard with lovely little streets and nooks to explore; and the local shops, market days, restaurants provide everything needed locally. The property is adequate, a little rustic, but well suited to time outdoors by the lovely pool and as a springboard for day trips throughout amazing Tuscany....
United Kingdom
Olivier B.
The price is €153
includes taxes & fees
22 Dec - 23 Dec
panoramica casa con piscina privata
Property grounds
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 €147
includes taxes & fees
6 Jan - 7 Jan 2026
san gimignano apartment in historical center, courtyard and fast free wifi
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

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!