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Featured holiday rental destinations

Destination inspiration for your trip – find a holiday rental

Siena

387 holiday rentals

San Gimignano

218 holiday rentals

Montepulciano

193 holiday rentals

Gaiole in Chianti

115 holiday rentals

Montalcino

89 holiday rentals

Pienza

78 holiday rentals

Rapolano Terme

61 holiday rentals

Poggibonsi

59 holiday rentals

Castelnuovo Berardenga

58 holiday rentals

Radda in Chianti

50 holiday rentals

Castellina in Chianti

49 holiday rentals

San Quirico dʼOrcia

48 holiday rentals

Monteriggioni

43 holiday rentals

Sarteano

40 holiday rentals

Castiglione dʼOrcia

40 holiday rentals

Asciano

40 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.

K
Kwee Ming
From
Singapore
Everything. We love the garden view from our room, room facilities, the breakfast, the location.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 2,047 reviews
Price from
US$127.77
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.

T
Tornike
From
Bulgaria
Amazing city, great location, if you wonder where to book in Siena, definitely this is the place. Pietro is a wonderful host. So helpful and with so many detailed useful information. Room was clean, very cozy, there is also and extra room for everyone to use with coffee and terrace. really enjoyed our stay in Siena, will definitely visit again with pleasure.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 1,256 reviews
Price from
US$132.81
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.

K
Ksenia
From
Spain
Very welcoming hosts - make you feel really at home, very clean room with amenities ( like slippers, teapot etc), great breakfast. We felt like we wanted to come back every day!
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 1,149 reviews
Price from
US$120.83
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.

A
Ausra
From
Norway
We had an amazing experience from the moment we arrived to when we left. The service, the atmosphere and place was breathtaking. Food and wine was amazing. Apartment was lovely with great space and comfort. In general we are very pleased and happy to have stayed at Villa Nottola and will definitely be returning!
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 2,103 reviews
Price from
US$124.56
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.

D
Daniela
From
Romania
Very good location, personal very nice and helpful, fast check-in, nice room with Italian vibe, clean.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,819 reviews
Price from
US$93.55
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.

K
Kirsty
From
Belgium
It’s a beautiful location, very peaceful but so close to the centre of Siena. The staff were very friendly and helpful. The rooms had a lovely Italian charm which made for a great nights sleep. We only stayed one night but wished we had spent longer.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,845 reviews
Price from
US$116.10
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.

P
Paul
From
Malta
Quiet, clean and beautiful surroundings.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,259 reviews
Price from
US$138.63
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.

S
Stefanie
From
Belgium
Everything was great, views, rooms, host, top!
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 326 reviews
Price from
US$104.06
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.

k
karen
From
United States
Ideal location in the beautiful hilltop town of historic Montepulciano.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 116 reviews
Price from
US$195.64
1 night, 2 adults

Casa nel centro storico

San Gimignano City Centre, San Gimignano

Located in the centre of San Gimignano, 39 km from Piazza Matteotti and 44 km from Piazza del Campo, Casa nel centro storico offers free WiFi, a terrace and air conditioning.

J
Josh
From
Netherlands
Newly renovated, quiet at night, great location.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 111 reviews
Price from
US$221.13
1 night, 2 adults
All holiday rentals in Siena Area

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Popular with guests booking holiday rentals in Siena Area

Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 2,902 reviews

Popular with guests booking holiday rentals in Siena Area

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,845 reviews

Popular with guests booking holiday rentals in Siena Area

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 2,047 reviews

Popular with guests booking holiday rentals in Siena Area

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 2,103 reviews

Popular with guests booking holiday rentals in Siena Area

Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 1,273 reviews

Popular with guests booking holiday rentals in Siena Area

Scored out of 10, guest rating 7.0
Good - What previous guests thought, 1,728 reviews

Popular with guests booking holiday rentals in Siena Area

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 786 reviews

Popular with guests booking holiday rentals in Siena Area

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 1,256 reviews

Popular with guests booking holiday rentals in Siena Area

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 830 reviews

Popular with guests booking holiday rentals in Siena Area

Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 1,067 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, 407 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
Avg. price/night: US$153.20
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 181 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, 580 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, 278 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 9.6
Exceptional - What previous guests thought, 92 reviews
Several (small) holiday appartments/houses, offering a lot of privacy though, with nice and authentic decoration, and with airconditioning (a bless with temperatures reaching between 34 and 38°C). Wonderful place to stay, in a huge wild garden on a hill, with a swimming pool, near to the small village of Le Piazze. Very friendly, enthousiastic and helpful hosts, who also provide fresh bread for breakfast.
Guest review by
Dieter
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, 135 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, 168 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, 952 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