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

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171 Holiday homes

Apartment letting in Siena

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £103 / night

£515 / week

1 / 29

Holiday cottage in Val di Merse

Val di Merse cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Pricing unknown

1 / 13

Holiday villa rental

Siena villa

  • 11 bedrooms
  • 11 bathrooms
  • sleeps 24

from £1,260 / night

£8,816 / week

1 / 14

Siena holiday apartment rental

Siena apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

from £182 / night

£1,274 / week

1 / 4

Holiday villa with swimming pool in Siena

Siena villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 16

from £745 / night

£4,408 - £9,718 / week

1 / 233

Holiday villa with swimming pool in Siena

Siena villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

from £353 / night

£2,469 / week

1 / 14

Holiday villa in Siena

Siena villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £325 / night

£2,270 / week

1 / 19

Holiday home with swimming pool in Siena

Siena house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 10

from £674 / night

£5,575 / week

1 / 24

Holiday villa rental

Siena villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 17

from £1,876 / night

£13,132 / week

1 / 37

Holiday home with swimming pool in Siena

Siena house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £674 / night

£5,575 / week

1 / 16

Condo rental in Siena

Siena condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £118 / night

£823 / week

1 / 18

Holiday home with swimming pool in Siena

Siena house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £490 / night

£4,286 / week

1 / 24

Holiday b&b in Siena

Siena b&b

  • 4 bedrooms
  • 1 bathroom
  • sleeps 2

from £196 / night

£1,372 / week

1 / 13

Holiday farmhouse in Siena

Siena farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £303 / night

£2,119 / week

1 / 44

Holiday farmhouse in Siena

Siena farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £205 / night

£1,433 / week

1 / 43

Holiday studio in Siena

Siena studio

  • Studio
  • 1 bathroom
  • sleeps 4

from £69 / night

£343 - £480 / week

1 / 10

Holiday apartment in Caprera

Caprera apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Pricing unknown

1 / 10

Holiday apartment in Siena

Siena apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £128 / night

£892 / week

1 / 22

Holiday apartment in Siena

Siena apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £93 / night

£578 / week

1 / 17

Holiday apartment in Siena

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

Pricing unknown

1 / 46

Siena holiday farmhouse rental

Siena farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £108 / night

£755 / week

1 / 7

Holiday villa in Siena

Siena villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £560 / night

£3,919 / week

1 / 10

Holiday farmhouse in Siena

Siena farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Pricing unknown

1 / 20

Holiday apartment in Costalpino

Costalpino apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £69 / night

£441 / week

1 / 12

Siena holiday b&b rental

Siena b&b

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from £54 / night

£378 / week

1 / 15

Siena holiday home rental

Siena house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £98 / night

£686 / week

1 / 4

Holiday apartment in Siena

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Pricing unknown

1 / 49

Holiday apartment in Siena

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Pricing unknown

1 / 47

Siena holiday townhouse accommodation

Siena townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £103 / night

£569 / week

1 / 56

Holiday farmhouse with shared pool in Siena

Siena farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £103 / night

£720 / week

1 / 5

B&b accommodation in Siena

Siena b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £127 / night

£885 / week

1 / 15

Villa rental in Siena with shared pool

Siena villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £238 / night

£1,667 / week

1 / 16

Siena holiday apartment rental

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £55 / night

£384 / week

1 / 17

Siena holiday apartment rental

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £68 / night

£474 / week

1 / 17

Siena holiday apartment rental

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £74 / night

£515 / week

1 / 17

Holiday apartment rental

Siena apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

from £85 / night

£590 / week

1 / 19

Siena holiday villa rental

Siena villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £98 / night

£686 / week

1 / 14

Holiday apartment in Siena

Siena apartment

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 4

from £363 / night

£2,351 / week

1 / 19

Siena holiday villa rental

Siena villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

from £343 / night

£2,054 - £3,380 / week

1 / 50

Siena holiday finca rental

Siena finca

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £157 / night

£1,097 / week

1 / 5

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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

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
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
Stunning Tuscan views from traditional farmhouse 10mins to downtown Siena
Belvedere e stupendo

After a beautifully green, bus ride from Rome, I arrived at my designated stop a few kilometer’s before Siena and waited for my transfer to Belvedere, a magical home at the end of a beautiful long winding driveway where views of ‘Siena’s Il Duomo and the vineyards stretch as far as the eye can see. Belvedere has it all, the entertainment area with a barbeque area perfect for entertaining, an outside pizza oven, for easy suppers, and a beautiful antique dinner table for 10, beside a great fire place in case a dinner party in the middle of Tuscany takes your fancy. My personal favourite corner was the kitchen, with its cozy booth seat, where we all congregated each morning. The kitchen is so well equipped with all the conveniences you could wish for if cooking in numbers. There are three guest bedrooms, with lovely furnishing each with private en-suite which was a surprise and not a common finish in most guest houses. My second favourite spot was quite literally ‘Under the Tuscan Sun’ stretched on the sun chairs, with nothing more than the sound of a few bees. The guest handbook is impressive, with wonderful insight on the destination, and how to feel right at home. The owners have even taken the time to detail the best ways to conserve energy – Kudos You can also purchase wine and curio from the owners estate. I don’t think I could have asked for a better introduction to Tuscany, its’ beauty surpassed all expectation, and the comfort of feeling right at home will not be forgotten. I can definitely recommend Belvedere, as the perfect getaway for a couple or a few couples / friends and hope someday I will return. Bellisimo!see more
Anne
Very nice

Very nice flat in the city center. Welcoming perfect, and there Wonderful hosts and a fantastic spot for getting away from it allis a free parking 100 meters far. … see more
Elegant 2 bedroom apt in historic Siena residence-Very central near Campo Square
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 apartment in 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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