Vacation Rentals & Apartments in Siena

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1,697 apartments

Suite Il Tinaio. Villa Caprera, Siena Farmhouse.

Siena villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$162

One Bedroom Villa at Castello di Montalto in Chianti

Siena villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$174

Villa with Pool and Jacuzzi private Deal 2024

Siena villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$124

Tuscany Villa with pool - Villa le Capanne holday in private villas

Siena villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

“Fantastic Hosts for this unique countryside Villa” Our trip to Italy still fresh in our minds so we wanted to write to tell others about our lovely experience at Villa le Capanne. We stayed with another couple for one week, make trips to Florence, Voltera, Pisa and more. Gina and Franco met us and welcomed us with enough goodies to keep us well taken care of until we could shop. Each day, a new treat appeared and they were all yummy-Gina is a fantastic baker and cook. The villa was spotless and just as described. Let me just say that the location is a bit of a challenge, but worth it for the views. Sitting around the pool and gazebo was very relaxing. You may need to allow extra time to get to the main roads for day trips but if you are prepared, it is not a problem. We had some great fun at the local restaurant, pizza on the weekend and then dinner on another night. The little village, Montecastelli Pisano was charming and we walked on a quiet street and found a violin maker who played us one of his own compositions-unique experience! Great hosts in a lovely setting!

Responds fast! avg. 2 hours 23 minutes

Price per night from

$116

Casa Borgianni. Villa Caprera, Siena Farmhouse.

Siena villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“heavenly” A beautifully appointed home, with mercifully two batherooms, tastefully decorated with all that you need. The kitchen is a dream - everything you need. Lovely crockery, not bottom-of-the-range, and the bed linen also of excellent quality. Easy access to Siena, on the bus-route - useful to go into Siena by bus, because parking can be a nightmare in Siena itself. Lovely view of Siena, from the top floor. So all in all, this is a hard place to beat, if you want a few days, or longer, just to chill-out and relax and you would be forgiven for thinking Maggie Smith is going to come walking up the drive-way...

Price per night from

$298

Castello di Montalto - 3 Bedroom Villa in Chianti

Siena villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$411

Price per night from

$1,432

Live Siena from the very top

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$113

2 Bedrooms Flat Crete Senesi

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$59

Suite Le Camelie

Caprera apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$149

montechiaro Shed

Siena house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$621

Responds fast! avg. 2 hours 23 minutes

Price per night from

$133

Responds fast! avg. 2 hours 15 minutes

Price per night from

$282

Homey 3 Bedroom Apartment in the Hills of Siena

Siena apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$143

Apartment Tinaia

Siena apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$302

Villa la Strega

Siena villa

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$998

Abbadia di Siena 12

Siena house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$585

BNB PAOLINA King Room with Garden View

Siena b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$208

BNB PAOLINA Deluxe Room

Siena b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$160

montechiaro Tower

Siena house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$854

montechiaro Hut

Siena house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 10

Price per night from

$854

Tettoia Apartment

Siena apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$248

Casa di roberto

Siena b&b

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

Price per night from

$69

Price per night from

$342

Villa Limonaia

Siena villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$302

TuscanFlat

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 44 minutes

Price per night from

$174

Villa Caprera Suite Le Camelie

Caprera apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$149

ACCOMMODATION IN VILLA TOSCANA

Siena apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 54 minutes

Price per night from

$118

Siena historic centre apartment Mimosa

Siena condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$149

Bright, spacious apartment in Villa with pool near Siena

Siena villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$354

Stunning Tuscan views from traditional farmhouse 10mins to downtown Siena

Costalpino villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$309

Elegant three bedroom Tuscan-style apartment to re

Val di Merse apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$286

Appartamento Bilocale con piscina sulle colline di Siena

Isola d'Arbia farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$115

Borgo Villa Certano - Poggiolo

Costalpino farmhouse

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 54 minutes

Price per night from

$106

Apt. 4pax- 1 bedroom (2km from city centre)

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Price per night from

$187

Villa Caprera. Casa Borgianni

Caprera farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$298

Villa Caprera. Tinaio

Monastero farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$162

Siena holiday apartment rental

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$131

Viewing 38 of 1,697
rentals in Siena

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About Siena

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, travelers 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 center.

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 vacation 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

Exclusive Tuscan Villa with pool,hot tub,A/C,7 bd, free wi-fi,15 km from Siena
Perfect in every way!!!

What can I say….???We have already decided to book this Villa for next year…..one week is not enough, we will be back Villa "Le Caggia" was the setting for a fabulous vacation with our family. The location was perfect as we could take a number of day trips to explore Tuscany, from Florence(one hour driving) to Siena(20 minutes) and many other lovely towns in the Chianti or in the Orcia valley Waking up in the morning to see the fields spread below us was absolutely incredible, the Villa is spacious, very clean and decorated with care in every detail. A huge garden with a beautiful swimmingpool where you can relax while sipping a good Chianti wine, always cherished by the magical breeze(it is a Le Caggia trademark that you can only find here) ever-present and pleasant. Last but not least, Fabio e Jacopo were terrific hosts, always helping us, have made our stay more enjoyable and memorable…. Absolutely do not miss their welcome dinner and their cooking class….I already used their recipes to prepare a dinner and I have delighted all my friends, friends that will be with us for the second time at Le Caggia Absolutely the perfect place for those who want to enjoy Tuscany.see more
Casa Borgianni. Villa Caprera, Siena Farmhouse.
A perfect Tuscan retreat

We have just returned from Italy, the first week of which was spent at Villa Caprera. We already loved Tuscany, as we have been twice before. However, nothing prepared us for the wonderful find of Villa Caprera, and we didn't want to leave. The location is perfect for our beloved Siena, and is in the heart of rural tuscany. The booking was efficient, and queries dealt with quickly and in a friendly, helpful manner by Simona. We arrived to the warmest of welcomes from Daniella, with lots of homely touches like homemade cake, wine, milk, olive oil and balsamic. The villa itself is beautiful: clean, tasteful, comfortable and full of love. Everything we required was provided, and more. Fresh vegetables and fruit were brought to us by lovely Daniella, and we couldn't have asked for more. It is even more beautiful than the photographs suggest. We will definately be returning to Villa Caprera. Thank you so much Daniella and Simona for everything.see more
Tuscany Villa with pool - Villa le Capanne holday in private villas
Beautiful villa and amenities exceptional

I stayed at Le Capanne from 4 - 11 June 2016 with my husband, stepson and his partner. The property was superb and the best equipped I have ever stayed in. Gina and her husband are lovely people and went out of their way to help such as advising on travelling to nearby towns and making a restaurant reservation for us. Gina left a pannacotta and bread for us during our stay which was a really lovely gesture as well as a nice welcome basket of foodstuffs.The location was superb, as was the pool and hot tub which was used many times. We enjoyed having a barbecue one evening in the garden.The property and grounds were very well cared for. We did not have to worry about anything except enjoying our holiday. We visited Siena, San Gimignano ( a must visit), Florence and Pisa. We all agreed it was one of the best holidays we have ever had and we all would love to return again in the future. I recommend this villa without hesitation. Thank you so much to Gina and Franco for a great holiday.see more

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