Vacation Rentals & Apartments in Siena

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3,118 apartments

Villa Caprera, Siena Farmhouse. Suite Il Tinaio

Siena villa

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$114

One Bedroom Villa at Castello di Montalto in Chianti

Siena villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$139

2 Bedrooms Apartment (Ambrosia)

Siena apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$69

Abbadia di Siena

Siena house

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$278

Villa with Pool and Jacuzzi private Deal 2019

Siena villa

2 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 46 minutes

Price per night from

$118

GAIA FOUND

Siena apartment

2 bedrooms / 1 bathroom / sleeps 3

Price per night from

$125

La Senesina , enchanting apartment near Siena

Siena apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$89

2 Bedrooms Apartment (Belladonna)

Siena apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$69

Castello di Montalto - 3 Bedroom Villa in Chianti

Siena villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$306

Independent villa with private pool in Siena countryside - 3 bedrooms

Siena villa

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 1 hour 34 minutes

Price per night from

$366

SIENA ROMANTIC

Siena apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$87

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

Siena villa

3 bedrooms / 3 bathrooms / sleeps 7

“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.

Responds fast! avg. 1 hour 4 minutes

Price per night from

$118

Gated Luxury Estate "LaChiusa" Prime Chianti Classico! Exquisite Privacy & Views

Siena farmhouse

4 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 50 minutes

Price per night from

$379

THE WAVE – 8bd with terrace behind Piazza del Campo

Siena apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$124

Villa Caprera, Siena Farmhouse. Casa Borgianni.

Siena villa

3 bedrooms / 2 bathrooms / sleeps 6

“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.

Price per night from

$234

Siena San Fabiano climatized villa with outdoor heated pool

Siena villa

6 bedrooms / 6 bathrooms / sleeps 21

“The Best Place to Celebrate your Birthday with Friends” Coming back to "San Fabiano" is like coming back to friends. If you wish to forget all your day-by-day problems, come to stay at this place. Located in the middle of the farm fields. Sit under the beautiful trees next to the pool and listen to the wind, and understand the value of the word tranquility. We were a party of three rooms, celebrating my round birthday. This is certainly not the last time they will see me at "San Fabiano".

Price per night from

$1,010

Live Siena from the very top

Siena apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$105

Luxurious Vacation Rental at Palazzo Cinotti in Si

Siena apartment

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$442

Palazzo Cinotti Suite Giulio

Siena apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$240

2 Bedrooms Flat Crete Senesi

Siena apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 55 minutes

Price per night from

$53

IL TOLOMEI central in the middle of main street

Siena apartment

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$119

Private Villa,Pool, Hot tub,A/C,WiFi,5BR,15km from Siena

Siena villa

5 bedrooms / 6 bathrooms / sleeps 12

“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.

Price per night from

$631

Suite Le Camelie

Caprera apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$114

MODERN SAN FRANCESCO

Siena apartment

2 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$127

Palio 2 - Charming Cosy Studio in Siena Center

Siena studio

Studio / 1 bathroom / sleeps 2

Price per night from

$90

montechiaro Shed

Siena house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$450

2 Bedrooms Apartments (Camelia)

Siena apartment

2 bedrooms / 1 bathroom / sleeps 5

“Wow!” When we arrived Fabio was waiting for us at the front door and gave us a wonderful introduction to his establishment and Siena. He gave us advice on where the best places were to eat at different budget levels and what were the most important sights to see in Siena all done over a cup of coffee. We stayed in the apartment B which was much bigger than I had expected and opened out onto a beautiful central square where we enjoyed to walk and have a glas or two of wine each evening. We were moving on to Montepulciano from Siena and Fabio kindly rang atound several different taxi and shuttle services to find the best price with a driver that he trusted which made moving on so much easier for us. After arriving in Montepulciano we realised we had left one of our bags in the taxi, so we rang Fabio who contacted him immediately and arranged for the driver to return. What more could you say, great place to stay, great friendly service I would certainly recommend this apartments to anyone staying in Siena.

Price per night from

$69

Authentic large 4BR farmhouse with community pool between siena + florence

Siena villa

4 bedrooms / 4 bathrooms / sleeps 14

“Love, Love, Love! Didn't want to leave!” My family and I travel quite frequently. For this trip, I wanted to enjoy my surroundings and family. So, we found this villa. With its spacious rooms, rolling hills and large pool we were in heaven. Also, this is really a working farm, so my youngest could enjoy playing with the sheep and other animals (Ulrike supervised). We took the night hike to dinner with Ulrike and the others and it was so much fun. She also kept us supplied with wine every evening! This villa is an easy hike to the center of the closest town but I would recommend a car for your stay. We took day trips to Siena, Florence, local wineries and other local towns. What I liked best: Ah, the air & scenery & wine! Least: I wish I had read through all of Ulrike's tips in the red folder. She has a lot of suggestions that I read about too late in our trip.

Responds fast! avg. 3 hours 47 minutes

Price per night from

$354

THE NEST OF MANGIA

Siena apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$87

Responds fast! avg. 1 hour 4 minutes

Price per night from

$127

Charming studio flat in the center of Siena

Siena studio

Studio / 1 bathroom / sleeps 4

Price per night from

$89

Homey 3 Bedroom Apartment in the Hills of Siena

Siena apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$146

Apartment Tinaia

Siena apartment

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$307

Villa la Strega

Siena villa

7 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$586

Luxury villa Reginetta

Siena villa

5 bedrooms / 5 bathrooms / sleeps 13

Price per night from

$496

Luxury villa Caselletto

Siena villa

5 bedrooms / 6 bathrooms / sleeps 10

Price per night from

$977

Abbadia di Siena 12

Siena house

5 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$363

Luxury villa Casina

Taverne d'Arbia villa

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$606

Viewing 38 of 3,118
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.