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Villas in Siena and Apartments - Holiday Lettings - Holiday Rentals Siena

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3,852 Holiday homes

Apartment rental in Siena

Siena apartment

1 bedroom / 1 bathroom / sleeps 4

23

from £113 / night

£1,150 / week

Caprera holiday apartment rental

Caprera apartment

1 bedroom / 1 bathroom / sleeps 2

2

Responds fast! avg. 3 hours 21 minutes

from £93 / night

£551 - £582 / week

Holiday apartment in Siena

Siena apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 35 minutes

from £98 / night

£606 / week

Holiday villa rental

Siena villa

3 bedrooms / 2 bathrooms / sleeps 5

9

Responds fast! avg. 2 hours 36 minutes

from £227 / night

£1,220 - £3,063 / week

Condo rental in Siena

Siena condo

1 bedroom / 1 bathroom / sleeps 4

14

from £87 / night

£594 - £881 / week

Holiday villa with shared pool in Siena

Siena villa

4 bedrooms / 2 bathrooms / sleeps 4

1

from £180 / night

£1,257 / week

Holiday apartment rental

Val di Merse apartment

3 bedrooms / 3 bathrooms / sleeps 7

6

Responds fast! avg. 1 hour 42 minutes

from £206 / night

£1,129 - £1,437 / week

Holiday villa with swimming pool in Siena

Siena villa

3 bedrooms / 2 bathrooms / sleeps 7

6

from £191 / night

£1,159 - £2,194 / week

Holiday apartment in Siena

Siena apartment

1 bedroom / 1 bathroom / sleeps 5

from £61 / night

£424 / week

Holiday apartment with swimming pool in Siena

Siena apartment

1 bedroom / 1 bathroom / sleeps 4

10

Responds fast! avg. 1 hour 19 minutes

from £119 / night

£740 - £1,217 / week

Isola d'Arbia holiday farmhouse rental

Isola d'Arbia farmhouse

1 bedroom / 1 bathroom / sleeps 4

from £206 / night

£1,437 / week

Holiday villa in Costalpino

Costalpino villa

3 bedrooms / 4 bathrooms / sleeps 8

14

Responds fast! avg. 3 hours 39 minutes

from £257 / night

£1,648 / week

Holiday apartment in Siena

Siena apartment

1 bedroom / 1 bathroom / sleeps 4

from £98 / night

£683 / week

Holiday farmhouse in Costalpino

Costalpino farmhouse

2 bedrooms / 4 bathrooms / sleeps 4

Responds fast! avg. 3 hours 35 minutes

from £71 / night

£495 / week

Holiday apartment in Val di Merse

Val di Merse apartment

1 bedroom / 1 bathroom / sleeps 2

2

Responds fast! avg. 1 hour 42 minutes

from £72 / night

£462 - £616 / week

Siena holiday farmhouse rental

Siena farmhouse

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 19 minutes

from £119 / night

£739 - £1,236 / week

Holiday apartment in Siena

Siena apartment

1 bedroom / 1 bathroom / sleeps 3

3

Responds fast! avg. 2 hours 43 minutes

from £78 / night

£464 - £680 / week

Holiday apartment in Val di Merse

Val di Merse apartment

6 bedrooms / 3 bathrooms / sleeps 14

1

Responds fast! avg. 1 hour 42 minutes

from £308 / night

£2,053 - £2,566 / week

Holiday home in Siena

Siena house

1 bedroom / 1 bathroom / sleeps 4

11

Responds fast! avg. 3 hours 19 minutes

from £98 / night

£667 - £839 / week

Farmhouse rental in Caprera

Caprera farmhouse

3 bedrooms / 2 bathrooms / sleeps 6

8

Responds fast! avg. 3 hours 21 minutes

from £190 / night

£1,129 - £1,314 / week

Apartment rental in Siena

Siena apartment

1 bedroom / 1 bathroom / sleeps 3

7

from £103 / night

£719 / week

Apartment rental in Siena

Siena apartment

1 bedroom / 1 bathroom / sleeps 5

4

from £62 / night

£433 / week

Holiday apartment in Siena

Siena apartment

2 bedrooms / 4 bathrooms / sleeps 4

2

from £380 / night

£2,463 / week

Siena holiday apartment rental

Siena apartment

2 bedrooms / 2 bathrooms / sleeps 4

1

from £81 / night

£512 - £800 / week

Holiday cottage in Siena

Siena cottage

1 bedroom / 1 bathroom / sleeps 2

23

from £121 / night

£848 / week

Holiday apartment rental

Siena apartment

1 bedroom / 1 bathroom / sleeps 4

4

from £98 / night

£680 - £1,118 / week

Apartment letting in Siena

Siena apartment

1 bedroom / 1 bathroom / sleeps 2

from £108 / night

£539 / week

Siena holiday townhouse accommodation

Siena townhouse

1 bedroom / 1 bathroom / sleeps 2

4

from £71 / night

£493 / week

Monastero holiday farmhouse let

Monastero farmhouse

1 bedroom / 1 bathroom / sleeps 4

2

Responds fast! avg. 3 hours 21 minutes

from £103 / night

£611 - £642 / week

Villa rental in Siena with swimming pool

Siena villa

7 bedrooms / 7 bathrooms / sleeps 16

4

from £461 / night

£3,584 - £6,348 / week

Holiday apartment with shared pool in Siena

Siena apartment

1 bedroom / 1 bathroom / sleeps 2

from £72 / night

£503 / week

Holiday villa with swimming pool in Siena

Siena villa

7 bedrooms / 7 bathrooms / sleeps 16

Responds fast! avg. 2 hours 51 minutes

from £718 / night

£2,255 - £7,565 / week

Holiday apartment in Costalpino

Costalpino apartment

1 bedroom / 1 bathroom / sleeps 2

from £72 / night

£462 / week

Siena holiday apartment rental

Siena apartment

2 bedrooms / 1 bathroom / sleeps 4

6

from £82 / night

£513 - £800 / week

Siena holiday farmhouse rental

Siena farmhouse

1 bedroom / 1 bathroom / sleeps 2

from £113 / night

£790 / week

Apartment rental in Siena

Siena apartment

2 bedrooms / 1 bathroom / sleeps 6

12

from £73 / night

£361 - £701 / week

Siena holiday finca rental

Siena finca

1 bedroom / 1 bathroom / sleeps 4

from £165 / night

£1,150 / week

Home rental in Siena

Siena house

3 bedrooms / 2 bathrooms / sleeps 7

6

from £155 / night

£1,019 / week

Holiday townhouse in Siena

Siena townhouse

2 bedrooms / 3 bathrooms / sleeps 4

3

from £380 / night

£2,514 / week

Holiday apartment in Siena

Siena apartment

2 bedrooms / 1 bathroom / sleeps 4

4

from £86 / night

£483 - £741 / week

Viewing 40 of 3,852
rentals in Siena

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Siena holidays

Siena is a classic 13th century Italian village in the hills of the Tuscan countryside. Its wealthy golden era took place between 1200 and 1300 AD and much of its art and architecture still bears the signature of this medieval period. For centuries, travellers have been coming to Siena for its beauty and history, its unusual piazza, its religious pilgrimage sites, and its famous summer horse races that take place in the market square. Visitors also come here to experience the romance of Tuscany. While you're here, wander the curious side streets, rest your feet beside ornate fountains, and stroll the galleries of Siena's fascinating art museums. Don't miss the gothic town hall building, and make sure you also find time to explore the hills and vineyards beyond the village centre.

Here are some suggested things to do and see on your visit to Siena:

  • Take a culinary and winery tour: There are several tours available in Siena that can take visitors from one Tuscan vineyard to another and offer culinary sampling from some of Siena's world-class restaurants. This is a wonderful opportunity to take in the legendary countryside and experience the delicious traditions of this region.
  • Take a Tuscan cooking class: Immerse yourself in Tuscany's culinary traditions by taking a cooking class. Many available courses are taught by accomplished Italian chefs.
  • Visit the Siena Cathedral: Many visitors consider this the most beautiful religious site in Italy. Observe the classic Gothic architecture and intricate carvings of the exterior.
  • See the Piazza del Campo: As the heart of Siena, this is an excellent starting point for a walking tour of the city. If you visit during July and August, the square will be alive with noise and excitement surrounding the Palio horse races that take place here.
  • Visit the Torre del Mangia: For breathtaking views of the city and surrounding landscape, climb the Tower of Mangia. Constructed in 1325, the tower rises up about 290 feet.
  • Explore the National Archeological Museum of Siena: This building itself is a destination. Originally constructed as a pilgrim's hostel, it has been a hospital since the 10th century.

No matter what time of year you plan to arrive here, you'll have no trouble finding a holiday rental that meets your needs. In the heart of the village, within reach of the town square, you can book a condo or apartment in what may be a 13th century structure. You can also easily rent a beautiful Tuscan villa with views of the city or the rolling inland hills.

Top Destination reviews

A Jewel in Siena
A very good apartment

A very good and big apartment in a quiet area - close to the historical towncenter. Shops and restaurants in the neighbourhood. Comfortable rooms, big kitchen/diningroom, beautiful outdoor areal, a fine familyhome - and a kind hostess. … see more
TuscanFlat
The best view of any apartment I have stayed in-worldwide

The apartment is in the perfect location 5 minutes from the Campo, 30 seconds to a supermarket and less than a minute to a huge variety of restaurants, bars, ice cream parlours and so on. We never needed public transport once and walked to every corner of the city. The owner was very responsive to message before and during the stay and was very helpful with instructions and recommendations for local eateries. The apartment is small but it was absolutely fine for us, a married couple. The Air Con was good, the shower worked well and the bed and bedding were comfortable. Apartment was clean on arrival. Good facilities like a powerful hairdryer, coffee machine and a good oven were provided. We did not use the Hot Tub but it was provided. The real star of the show is the top balcony. It has a 360 degree view of the city, one direction to the Tuscan hills, the other to the Campo and Duomo. Incredible. We sat there at 6.30am, midday, 5pm and 10pm, every time a different light making it more spectacular. I could sit on that balcony all day long (although it was hot in July!) The chairs provided on the balcony are a little function over comfort but this is not unusual for Italy. A few more chair cushions might have helped. The loungers are fine and comfortable. As previous reviewers have said there is two flights of stairs into the apartment so you would need to be mobile to access all areas. The lift takes you up and down to the outside if you choose. It is strangely slow however so give yourself at least 5 minutes from doorway to outside! I would recommend this apartment and I would stay here again without question. The perfect site to explore everything the beautiful Siena has to offer.see more
Villa private pool, tennis, relaxing, luxury in Siena, Chianti, Tuscany, Italy
Ms

A wonderful villa set on top of a hill with very kind and attentive hosts. They have an eye for detail and a strong goal to deliver a clean fully functioning villa so that you can relax and it works! We spent two weeks here and just got so relaxed that after the first week and the excitement of the Palio, we stopped going to Siena every day and started hanging out at the beautiful pool area. Lazy I know but with such a beautiful view it is hard to resist. Andrea, his wife Elizabetta, and their son Thiago do a great job together. Each has their role. They leave you alone if you are comfortable on your own but if you want something they are there to help in an instant. Their house is the main villa on the property and their front door approachable so you can find them when you need or just say ciao and walk to the pool. It is up to you and they make you feel like you can choose either option depending on your day. They do a really good job as hosts. As for the villa the photos are accurate. I have gone back and checked and what you see in those shots is exactly how it looks. Note the clean modern kitchen and bathrooms. You might not appreciate quite how large the upstairs bedrooms are. They are huge airy and very comfortable with aircon. The downstairs bedroom is best for a child. A flyscreen on the bigger window in this room would help in the hottest part of summer. We would return here and wish the family all the best. Heathersee more
Castello di Montalto - 3 Bedroom Villa in Chianti
Beautiful hideaway

We stayed here for 2 weeks and had an amazing time. Beautiful castle in idyllic setting with really authentic feel. Lovely people in charge who made us feel welcome. Only very minor comments would be that some of the equipment needs an upgrade - bikes weren’t really fit for purpose, lights in bbq area didn’t work, bbq equipment not great Overall a place I would return to.see more
Elegant 2 bedroom apt. in historic Siena residence
Beautiful historic apartment!

The apartment is beautiful, in a historic tower that was built prior to 1070. The views from the apartment are stunning. Great location in city center, on a pedestrian street. Andrea was wonderful to communicate with and met us upon arrival. When in Siena, we recommend this apartment. … see more
Bright, spacious villa with pool near Siena
A charming Tuscan farmhouse villa

We stayed here for a most enjoyable week in September 2016. It is all that the owner Giada describes and she is a charming and helpful host. The villa, a converted stone farmhouse, is located on the outskirts of Siena, close to Quercegrossa. It is set in farmland and boasts an olive grove and a great swimming pool. There is ample car parking and immediate access to the Chianti wine region and the charming heritage sites of Tuscany.see more

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