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Featured holiday rental destinations

Destination inspiration for your trip – find a holiday rental

Siena

388 holiday rentals

San Gimignano

213 holiday rentals

Montepulciano

195 holiday rentals

Gaiole in Chianti

115 holiday rentals

Montalcino

90 holiday rentals

Pienza

77 holiday rentals

Rapolano Terme

60 holiday rentals

Castelnuovo Berardenga

58 holiday rentals

Poggibonsi

57 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.

N
Natasha
From
New Zealand
The view out the window was so beautiful! We also loved the breakfast - it had a great selection! Location is also amazing!
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 2,048 reviews
Price from
US$127.09
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.

K
Katerina
From
Greece
Pietro for the win! Amazing!!! Best tips for Siena
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 1,256 reviews
Price from
US$119.41
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, 1,150 reviews
Price from
US$120.19
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.

c
craig
From
Australia
everything was great, staff, facilities, food, location etc
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 2,103 reviews
Price from
US$123.91
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.

M
Mahesh
From
India
This is a 400 year heritage building that one will be staying. It's on the 2nd and 3rd floor. While there are no elevators, sometimes staff is there to help in getting the luggage up. Room size are comfortable. Our room had a windows one could open. The check in was very smooth and since they had rooms they gave us early check in easily. ROBERTO Is the master of ceremonies here. You ask anything he is there to help. Breakfast is cozy and nice. It's not very large.but it's what one needs. Boiled eggs. Breads. Desserts. Great coffee. Juices. Cold cuts. Cheese. Spreads. Bread with toaster. Featured yogurt. Etc etc. Good breakfast. They even packed breakfasts for us because two days we were going early. Which is very sweet of them. And this they did it proactively. There is a code for main door and also the floor entry. Shower pressure was superb. Also was the hotel water. The room has a kettle with tea and coffee powders to use. The quality of towels is good. Quality of toiletries is excellent. They have a small shower but comfortable. A wc and a bidet and a wash basin. Beds/ mattress are comfortable. And quality of pillows is very good. Location. Is very very central next to San frasesco church and walking distance to all attractions. Lovely Irishman bar next door plus amazing restaurants all in walking distance. Really loved and will recommend to stay here.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,820 reviews
Price from
US$93.06
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.

F
Federico
From
New Zealand
A beautiful hotel where everything felt just right. Loved the bedroom and the bathroom facilities, simple but good selection of teas in the room and a snack. Outstanding breakfast, it had everything you could ask for. Loved the selection of cakes. Extremely helpful staff, from dinner recommendations to explanations about the decors of the breakfast room.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,844 reviews
Price from
US$115.49
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.

J
Jeremy
From
Czech Republic
It was a lovely village in the vineyards. A great family who looked after us. Nice pool, very peaceful location, very pleasant manners and infomrative hosts.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,259 reviews
Price from
US$137.90
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.

P
Pavel
From
Czech Republic
Position - the new residential area above the historical city of Montalcino. The historic city centre is easy reachable but you are far from the city noise.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 326 reviews
Price from
US$103.51
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, 115 reviews
Price from
US$194.61
1 night, 2 adults

Mansarda Brunelleschi

Staggia

Offering city views, Mansarda Brunelleschi is an accommodation located in Staggia, 21 km from Piazza del Campo and 33 km from Piazza Matteotti.

M
Marko
From
Serbia
Nice apartment with artistic touch to it
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 150 reviews
Price from
US$77.64
1 night, 2 adults
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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, 1,844 reviews

Popular with guests booking holiday rentals in Siena Area

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 2,048 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 7.0
Good - What previous guests thought, 1,724 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 9.1
Superb - What previous guests thought, 488 reviews

Popular with guests booking holiday rentals in Siena Area

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 782 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 8.4
Very good - What previous guests thought, 1,707 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$152.39
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, 579 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, 277 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, 169 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, 951 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