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

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427 Holiday homes

Apartment letting in Siena

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £102 / night

£507 / week

1 / 29

Holiday villa rental

Siena villa

  • 11 bedrooms
  • 11 bathrooms
  • sleeps 24

from £1,240 / night

£8,680 / week

1 / 14

Holiday villa with swimming pool in Siena

Siena villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 16

from £1,206 / night

£5,787 - £9,567 / week

1 / 233

Holiday villa with swimming pool in Siena

Siena villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

from £348 / night

£2,431 / week

1 / 14

Holiday villa in Siena

Siena villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £320 / night

£2,235 / week

1 / 19

Holiday home with swimming pool in Siena

Siena house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 10

from £664 / night

£5,489 / week

1 / 24

Holiday villa rental

Siena villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 17

from £1,847 / night

£12,930 / week

1 / 37

Holiday home with swimming pool in Siena

Siena house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £664 / night

£5,489 / week

1 / 16

Holiday home with swimming pool in Siena

Siena house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £543 / night

£4,220 / week

1 / 24

Holiday b&b in Siena

Siena b&b

  • 4 bedrooms
  • 1 bathroom
  • sleeps 2

from £193 / night

£1,351 / week

1 / 13

Holiday farmhouse in Siena

Siena farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £298 / night

£2,086 / week

1 / 44

Holiday farmhouse in Siena

Siena farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £202 / night

£1,411 / week

1 / 43

Holiday studio in Siena

Siena studio

  • Studio
  • 1 bathroom
  • sleeps 4

from £68 / night

£338 - £473 / 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 £145 / night

£1,013 / week

1 / 22

Holiday apartment in Siena

Siena apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £92 / night

£569 / 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 £106 / night

£743 / week

1 / 7

Holiday farmhouse in Siena

Siena farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Pricing unknown

1 / 20

Siena holiday home rental

Siena house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £97 / night

£675 / 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

Holiday farmhouse with shared pool in Siena

Siena farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £102 / night

£709 / week

1 / 5

Siena holiday apartment rental

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £69 / night

£480 / week

1 / 17

Siena holiday apartment rental

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £60 / night

£419 / week

1 / 17

Siena holiday apartment rental

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £70 / night

£486 / week

1 / 17

Holiday apartment rental

Siena apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

from £75 / night

£520 / week

1 / 19

Siena holiday villa rental

Siena villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £132 / night

£919 / week

1 / 14

Holiday apartment in Siena

Siena apartment

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 4

from £357 / night

£2,315 / week

1 / 19

Siena holiday villa rental

Siena villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

from £266 / night

£1,601 - £3,327 / week

1 / 50

Siena holiday finca rental

Siena finca

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £155 / night

£1,081 / week

1 / 5

Holiday farmhouse with shared pool in Siena

Siena farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £97 / night

£675 / week

1 / 8

Holiday apartment in Siena

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £66 / night

£459 / week

1 / 17

Holiday apartment in Siena

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £79 / night

£554 / week

1 / 16

Holiday apartment in Val di Pugna

Val di Pugna apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £55 / night

£385 / week

1 / 24

Holiday villa in Siena

Siena villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £126 / night

£791 - £926 / week

1 / 42

Siena holiday villa rental

Siena villa

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

from £266 / night

£1,858 / week

1 / 35

Holiday apartment in Caprera

Caprera apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £116 / night

£811 / week

1 / 34

Holiday villa with swimming pool in Siena

Siena villa

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 12

from £776 / night

£5,428 / week

1 / 43

Siena holiday apartment rental

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £66 / night

£459 / week

1 / 15

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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

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
Exclusive Tuscan Villa with pool,hot tub,A/C,7 bd, free wi-fi,15 km from Siena
Perfect villa in perfect location

I need to start to say thank you to Jacopo and Fabio that made our holiday and stay absolutely perfect. They were both so helpful and such a pleasure to liaise with, even if we arrived later than expected! The villa is amazing, beautiful and perfectly located. We travelled extensively through Tuscany, Siena, Florence, Chianti, Montepulciano and Pienza. You definitely need a car (and gps) for this area as there is so much to see and do. Jacopo and Fabio organised us a trip to a beautiful Castle, Castello di Brolio, and also cooked us a true Tuscany dinner which was AMAZING! The villa is beautiful and looks exactly as in the pictures on the website. Its design is well thought out and there is plenty enough bedrooms and space for the amount of people it can accommodate. The outside table is a winner and being ‘true’ South African we had many BBQ’s outside. The farmhouse is surrounded in beautiful farmland and is a treat for morning walks. I would definitely recommend this villa and would love to go back soon.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
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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