Vacation Rentals in Province of Siena

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Top Cities in Province of Siena

Our top choices for Province of Siena vacation rentals

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

Townhouse in Montepulciano

Meublé Il Riccio
9.8 out of 10, Exceptional, (86)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
$148 nightly
The price is $168
Jan 3 - Jan 4, 2026
Total with taxes and fees
Meublé Il Riccio

Residence in Montepulciano

Residenza Fabroni
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
$88 nightly
The price is $102
Jan 13 - Jan 14, 2026
Total with taxes and fees
Residenza Fabroni

Townhouse in Montalcino

B&B Le Scalette di Piazza
9.4 out of 10, Exceptional, (90)
"Great location and excellent staff. "
Canada
Jacek
B&B Le Scalette di Piazza

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
$153 nightly
The price is $174
Dec 29 - Dec 30
Total with taxes and fees
Il Battistero Siena - Residenza d'Epoca

Townhouse in Montepulciano

La Locanda di San Francesco
9.8 out of 10, Exceptional, (131)
"Great room-great staff-great location"
United States
Richard
$172 nightly
The price is $194
Dec 26 - Dec 27
Total with taxes and fees
La Locanda di San Francesco

Townhouse in Siena City Centre

B&B Il Corso
9.8 out of 10, Exceptional, (192)
"Safe, clean, close to all attractions"
Canada
Carlo
$97 nightly
The price is $111
Jan 7 - Jan 8, 2026
Total with taxes and fees
B&B Il Corso

Townhouse in Siena City Centre

Siena Vip
9.2 out of 10, Wonderful, (422)
"A great location!"
Canada
Cheryl
$88 nightly
The price is $101
Jan 6 - Jan 7, 2026
Total with taxes and fees
Siena Vip

Townhouse in Siena City Centre

B&B Palazzo del Magnifico
9.8 out of 10, Exceptional, (63)
"Great location. Room spacious and clean. Personnel friendly and great service walkable to best historic places. Could find something better "
United States
Rodolfo
$100 nightly
The price is $115
Jan 12 - Jan 13, 2026
Total with taxes and fees
B&B Palazzo del Magnifico

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
$66 nightly
The price is $77
Jan 13 - Jan 14, 2026
Total with taxes and fees
Abbadia Sicille Relais

Townhouse in Cetona

La Locanda Di Cetona
9.2 out of 10, Wonderful, (5)
"A lovely hotel and very welcoming staff. Cetona is a delight. "
Australia
Julian
La Locanda Di Cetona

Townhouse in San Gimignano City Centre

Palazzo al Torrione 2
9.2 out of 10, Wonderful, (107)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
$122 nightly
The price is $140
Jan 19 - Jan 20, 2026
Total with taxes and fees
Palazzo al Torrione 2

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
$150 nightly
The price is $172
Jan 7 - Jan 8, 2026
Total with taxes and fees
Hotel San Gregorio

Townhouse in Montepulciano

Bed & Breakfast Vicolo dell'Oste
9.6 out of 10, Exceptional, (128)
"Great hosts, central location "
United States
Alexander
Bed & Breakfast Vicolo dell'Oste

Townhouse in Gaiole in Chianti

L' Eroico
10.0 out of 10, Exceptional, (12)
"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."
United States
Perry
L' Eroico

Townhouse in Ravacciano

Domus il Palio B&B
9.2 out of 10, Wonderful, (81)
"Convenient for parking, clean and relatively easy access to the town. The rooms were functional, getting into the place after hours was easy ( check in). No breakfast but a supermarket was 300 meters away"
Canada
Marcus
$61 nightly
The price is $72
Jan 11 - Jan 12, 2026
Total with taxes and fees
Domus il Palio B&B

Townhouse in Pienza

Affitacamere Maria Gabriella
9.8 out of 10, Exceptional, (51)
"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "
United States
Lenise
Affitacamere Maria Gabriella

Residence in Montepulciano

Delcorto Suites
10.0 out of 10, Exceptional, (33)
"Exceptional service great building felt like a Medici!"
United States
gaetano
$199 nightly
The price is $224
Jan 4 - Jan 5, 2026
Total with taxes and fees
Delcorto Suites

Townhouse in Montalcino

Idolina Guest House
9.4 out of 10, Exceptional, (105)
"The room met our expectations. Fulvia welcomed us and provided all info we needed. She was lovely and the room spacious and cosy. The location was perfect for our needs and we were very pleased."
United Kingdom
Kathrin
Idolina Guest House

Aparthotel in Rapolano Terme

Podere La Chiusella
9.4 out of 10, Exceptional, (30)
"Et sjarmerende lite B&B. Har nok vært utrolig vakkert i sine glansdager, men områdene rundt bærer preg av lite vedlikehold. Leiligheten var helt grei for en overnatting. Gulvet på badet var ikke rent. Når vi tørket opp etter oss ble håndkleet møkkete. Men overnattingen var helt grei alt i alt. Når vi skulle sjekke ut var det ikke et menneske å se, resepsjonen var stengt. Endte med å sette nøklene i døra og dra da alt var betalt ved bestilling."
Norway
Elisabeth
Podere La Chiusella
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

Find out more about Province of Siena

Discover your perfect Province of Siena vacation rental with Expedia

How many vacation rentals are available in Province of Siena?


Expedia has plenty of vacation rentals to choose from in and around  Province of Siena, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Province of Siena?


The selection of Province of Siena vacation rentals we have selected for you start as low as $77 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Province of Siena?


Vacation rentals in Province of Siena come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Province of Siena vacation rentals to suit everyone. 


Why should I choose a vacation rental in Province of Siena?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Province of Siena vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Province of Siena?


Find vacation rentals in Province of Siena by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Province of Siena.  


What amenities are available in a vacation rental in Province of Siena?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Province of Siena vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Province of Siena?   


Everytime is a great time to head to Province of Siena! Staying in a Province of Siena vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Province of Siena. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Province of Siena vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Province of Siena, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Province of Siena vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.