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Siena

379 holiday rentals

San Gimignano

222 holiday rentals

Montepulciano

188 holiday rentals

Gaiole in Chianti

126 holiday rentals

Montalcino

86 holiday rentals

Pienza

76 holiday rentals

Poggibonsi

61 holiday rentals

Castelnuovo Berardenga

57 holiday rentals

Rapolano Terme

53 holiday rentals

Castellina in Chianti

51 holiday rentals

San Quirico dʼOrcia

49 holiday rentals

Radda in Chianti

49 holiday rentals

Monteriggioni

43 holiday rentals

Sarteano

40 holiday rentals

Asciano

40 holiday rentals

Chiusi

38 holiday rentals

The best holiday rentals in Siena Area

Check out our pick of great holiday rentals in Siena Area

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Il giardino di Pantaneto Residenza D'Epoca

Siena City Centre, Siena

Conveniently located in Siena, Il giardino di Pantaneto Residenza D'Epoca offers a continental breakfast and free WiFi.

a
alessandro
From
Poland
The place was very clean, the host was extremely friendly and helpful, and the breakfast was very nice. I had a wonderful stay and would definitely recommend it.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 2,033 reviews
Price from
US$160.23
1 night, 2 adults

Fattoria di Cinciano

Poggibonsi

Offering an outdoor pool and a restaurant, Fattoria di Cinciano is located in Poggibonsi, a 10-minute drive from the centre. Free WiFi access is available in all areas.

E
Esty
From
United Kingdom
the property is beautiful! the staff were so lovely, the room was perfect. the food at breakfast and in the restaurant was so so so good. and the wine just amazing! their olive oil is also the best i have ever had
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,011 reviews
Price from
US$108.76
1 night, 2 adults

B&B Il Corso

Siena City Centre, Siena

Just 40 metres from Siena’s Piazza del Campo, B&B Il Corso is located on the first floor of a 16th-century building. It offers free Wi-Fi and elegant rooms.

F
Francesca
From
Luxembourg
The host Pietro is super helpful in recommending what to do and where to eat. Room was super nice
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 1,253 reviews
Price from
US$121.87
1 night, 2 adults

Casa Di Campagna In Toscana

Sovicille

Set 9 km from Siena, this 19th-century country house features a restaurant and outdoor pool. It offers traditional Tuscan rooms with wood-beamed ceilings, surrounded by sunflower fields.

R
Roberta
From
Albania
Staff was super friendly, the room was very clean and had all necessary amenities. The breakfast was delicious.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 1,151 reviews
Price from
US$122.67
1 night, 2 adults

Villa Nottola

Montepulciano

Villa Nottola is a former noble residence in the countryside of Montepulciano, besides the namesake winery. It offers a sun terrace with swimming pool.

R
Rok
From
Slovenia
Room was big, bathroom hude with two sinks, lots of room, premium style. Breakfast good, dinner even better. Awesome location with big garden with romantic spots.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 2,103 reviews
Price from
US$126.46
1 night, 2 adults

B&B San Francesco

Siena City Centre, Siena

Set in a 15th-century building in the historic centre of Siena, B&B San Francesco is just opposite the Bruco Fountain, a 5-minute walk from Piazza del Campo. All rooms offer city views and free WiFi.

A
Adilbi
From
Kazakhstan
The room is very comfortable and spacious, with everything you need. The bed is very comfortable and soft. The service is top notch.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,820 reviews
Price from
US$90.07
1 night, 2 adults

Borgo Grondaie

Siena

Borgo Grondaie is a large property built out of an old Tuscan farm, just 2 km from the historical centre of Siena.

I
Imre
From
Hungary
I mean, this is a charming, fantastic place to be! What an atmosphere with all the olive trees, the pool, the flowers, the houses around. We were in a 2 bedroom apartment with 2 bathrooms and a beautiful kitchen area/living room. Very comfortable. Even we had a private garden where a breakfast is fantastic. They have a great selection of wines, so you can enjoy local drinks. There is a big shop 200 meters, so you can buy whatever you want. The city center is 30 mins walk, but also by car you can park at the gates, so no problem at all. The train station is 10 minutes walk, all major cities can be reached from there. We spent 10 days but we definitely would go back any time. Sig. Giovanni Gatto also was very friendly!
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,847 reviews
Price from
US$117.87
1 night, 2 adults

Agriturismo San Sano

Gaiole in Chianti

Set within 24 km of Piazza del Campo and 29 km of Piazza Matteotti, Agriturismo San Sano offers rooms with air conditioning and a private bathroom in Gaiole in Chianti.

b
brickD
From
South Korea
This place is absolutely amazing. The WHOLE VILLAGE (including this agritusmo) is just beautiful and peaceful. The food and wine were nice and tasteful. We can order this area wine per each vintage in glass wine. The pool was perfect and located right beside the winery yard. I have never seen such a big olive tree ever from my country so it was totally amazing experience for my family. People were warm and helpful. For 10days in Italy, this place was the best.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,263 reviews
Price from
US$127.83
1 night, 2 adults

Casa Vacanze la Pineta

Montalcino

Featuring a garden and views of city, Casa Vacanze la Pineta is a recently renovated apartment set in Montalcino, 42 km from Mount Amiata.

B
Balazs Attila
From
Hungary
Amazing view to the hills, refurbished and well equipped apartment. Private parking.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 333 reviews
Price from
US$105.65
1 night, 2 adults

Casa del Fauno

Montepulciano

Set in Montepulciano within 47 km of Mount Amiata and 5 km of Terme di Montepulciano, Casa del Fauno offers rooms with free WiFi. This guest house is 28 km from Bagni San Filippo.

J
Jasmin
From
Philippines
Our room was lovely and just as shown in the photos. Decor was very tasteful and I would have stayed longer if possible. Complimentary drinks and snacks were provided in the room which was a very welcome surprise.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 118 reviews
Price from
US$198.62
1 night, 2 adults
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Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 2,103 reviews

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Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,847 reviews

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Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 2,033 reviews

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Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 2,896 reviews

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Scored out of 10, guest rating 9.1
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Popular with guests booking holiday rentals in Siena Area

Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 1,285 reviews

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Scored out of 10, guest rating 7.0
Good - What previous guests thought, 1,722 reviews

Popular with guests booking holiday rentals in Siena Area

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 1,255 reviews

Popular with guests booking holiday rentals in Siena Area

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 1,003 reviews

Popular with guests booking holiday rentals in Siena Area

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 792 reviews

FAQs about holiday rentals in Siena Area

Holiday rentals that guests love in Siena Area

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Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 404 reviews
Beautiful views, very quiet location and comfortable stay. The pool was clean and the small playground on site, as well as the friendly cats kept our 4 year old very entertained. The restaurant at the sister villa was also good. We did self-catering so cannot speak for the breakfasts but the olive oil we bought on site was great!
Guest review by
Seemat
Family with young children
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 182 reviews
The beautiful views of vineyards and hills, we felt very welcome and on vacation. The appartment on two storeys was well decorated and the swimming pool very refreshing with a stunning view. Wow Tuscany at its best. The owners and their friendly dog were also nice. The village is closeby to get the grocery and that's where you do the check-in before arrival.
Guest review by
Caroline
Young couple
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 578 reviews
The location of the villa was perfect. The hosts were really kind and helpful.
Guest review by
Mónika
Young couple
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 279 reviews
Great host, very friendly and excellent service. Beautiful villa, amazing view from breakfast area (breakfast was great as well). Perfect location (close to Montepulciano, Pienza and other cities). Room was spacious, large bathroom/bedroom. highly recommended ! I would definitely return.
Guest review by
Wim
Young couple
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 41 reviews
Big and clean swimming pool, well-equipped house, great spot if you want to visit local towns and villages in Toscania. Each family has their own patio and even grill. Great contact with the owned who will respond to all your questions. My tip is to follow Elisa's directions instead of GPS (beacuse of Google Maps, i ended up on impassable, rocky road)
Guest review by
Jarosław
Family with young children
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 136 reviews
I like from the village to all the detail of the place. The host was so nice and kind that took care of us all the time. Even the restaurant near the place was fantastic!😆
Guest review by
Hyunkyung
People with friends
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 54 reviews
I loved everything about the villa. It was wonderful. And the hosts - Silvia and her gorgeous mother - were absolutely delightful. I couldn’t fault the beautiful apartment. It’s the best value accommodation I’ve ever booked in all my years of travel. My wife and my daughter feel exactly the same. Can’t wait to come back.
Guest review by
Scott
Family with young children
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 167 reviews
Great place on the ground floor. Large bedrooms, nice bathroom. A quiet place during the whole day . Excellent base point for exploring nearby towns and villages. Easy communication with Alessandro who gave us complete and detailed instructions regarding our stay (parking, keys...) We hope that in some future we will be back to this place.
Guest review by
Dusan
Family with young children
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 963 reviews
Wonderfull room and bathroom. Exceptionally clean. Very comfortable beds. Great A/C. Quiet. Excellent location. Provided a good boxed breakfast. Steffano was welcoming and provided a good restuarant recommendation - even made the reservation for us. The room was very well designed - they kept the old charm and had modern equipment/facilities. It was wonderful to stay inside a walled village. Would highly recommend.
Guest review by
Akil
Family with young children
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 2,103 reviews
A jewel among the wine yards. Spacious room, great breakfast and friendly staff. The restaurant at the hotel was fantastic. We stayed for 2 nights at the villa and both times dined there. Local wine and home made pasta were to die for.
Guest review by
Nadezhda
Young couple