Vacation Rentals & Apartments in Siena

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Suite Il Tinaio. Villa Caprera, Siena Farmhouse.

Siena villa

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$150

One Bedroom Villa at Castello di Montalto in Chianti

Siena villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$175

Villa with Pool and Jacuzzi private Deal 2023

Siena villa

2 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$125

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. 1 hour 37 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

$250

Castello di Montalto - 3 Bedroom Villa in Chianti

Siena villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$413

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

Siena farmhouse

4 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$1,431

Live Siena from the very top

Siena apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$104

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

$150

Palio 2 - Charming Cosy Studio in Siena Center

Siena studio

Studio / 1 bathroom / sleeps 2

Price per night from

$89

montechiaro Shed

Siena house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$466

“What a great time!!” Poderi Val Verde was the perfect place to celebrate our 25th wedding anniversary. There was 3 couples sharing the Casa Pineta Villa which provided us with plenty of space. The villa was well equipped, very clean - we were pleasantly surprised that it did not have a musty smell being such an old villa and the property was beautiful. Poderi Val Verde is located central to most attractions -Florence, Sienna, Cortona - (1.5 hours travel time)- we would leave in the morning for a day trip and then returned to the villa to enjoy the well kept property - the pool was the perfect spot for gathering to chat about our adventures and enjoy a refreshing swim before dinner. Casa Pineta allows for entertaining both inside and outside the villa. The kitchen had all the essentails for us to prepare our meals that we enjoyed overlooking the grounds and the beautiful view of the mountains. From the villa, you can also hike into the village of Castellina. Castellina has shopping, grocery stores and great gelato. Ulrike offers a welcome dinner which was delicous. She prepares a homemade feast of Italian cuisine including appetizers, pasta, wild bore,dessert and her own wine. It was the perfect way to unwind after a long day of travel. Thank you for such a wonderful time and we hope to visit again!!!

Price per night from

$348

Responds fast! avg. 1 hour 37 minutes

Price per night from

$134

Responds fast! avg. 2 hours 17 minutes

Price per night from

$245

Homey 3 Bedroom Apartment in the Hills of Siena

Siena apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$144

Cino Apartment B

Siena studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 21 minutes

Price per night from

$106

Apartment Tinaia

Siena apartment

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$304

Villa la Strega

Siena villa

7 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$1,002

Abbadia di Siena 12

Siena house

5 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$587

Experience history at Casa Vezzosa, in the heart of the city centre

Siena apartment

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$113

BNB PAOLINA King Room with Garden View

Siena b&b

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$209

BNB PAOLINA Deluxe Room

Siena b&b

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$161

montechiaro Tower

Siena house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$606

Piazza del Campo in Siena city center apartment for 2

Siena apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$275

montechiaro Hut

Siena house

6 bedrooms / 6 bathrooms / sleeps 10

Price per night from

$605

Tettoia Apartment

Siena apartment

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$250

Casa di roberto

Siena b&b

6 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$69

House near Siena with 4 bedrooms, up to 10 persons. Private pool and Wi-Fi!

Siena villa

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$343

Villa Limonaia

Siena villa

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$304

TuscanFlat

Siena apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 25 minutes

Price per night from

$106

Villa Caprera Suite Le Camelie

Caprera apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$125

ACCOMMODATION IN VILLA TOSCANA

Siena apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 16 minutes

Price per night from

$119

Siena historic centre apartment Mimosa

Siena condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$130

Bright, spacious apartment in Villa with pool near Siena

Siena villa

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$295

Stunning Tuscan views from traditional farmhouse 10mins to downtown Siena

Costalpino villa

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$311

Elegant three bedroom Tuscan-style apartment to re

Val di Merse apartment

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$250

Appartamento Bilocale con piscina sulle colline di Siena

Isola d'Arbia farmhouse

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$107

Viewing 38 of 1,971
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,5 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
Elegant 2 bedroom apt in historic Siena residence-Very central near Campo Square
Great Siena Flat

We had an excellent stay and experience with this flat. I would stay here again. First, Andrea was helpful in providing information on where to park, transportation options and personally met us when we arrived. He gave us a good orientation to the unit. It's located on the main street of Siena, close to everything. Andrea even pointed out favorite pastry shops and restaurants. High integrity guy. The flat was very clean and spacious. He provide extra sets of towels which was a plus. The unit has a washing machine and drying rack which we used and was helpful. He provided us some basic food to get started - yogarts, fruit juice. There's a great view from the dining room. The unit keeps a fairly even temp and just opening the windows gets a nice cross breeze. No screens on the windows but had no issues with bugs. As with any unit in the heart of the city, it's noisy if the windows are open. Closing them blocks most of the noise. The neighbors are quiet. The unit is on the 3rd floor. There's an elevator or about 100 stairs to climb. … 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
6 Bedrooms with Ensuite Baths, Pool, Wifi, Great Location
The villa exceeded our expectations!

It's difficult to believe that a villa will actually be as wonderful as you dream it will be-but this villa was just that. It is very comfortable with plenty of room for 12 adults plus two children, and villa layout and the grounds make it possible to really spread out. The wonderful owner made things very personal and special, it was within a day trip to many towns of note, and the closest village is very small and charming-exactly what we wanted. There is a very large table both inside and one outside that makes dining special, and we booked a pizza party as the villa has a wood burning oven which was a nice addition. Grounds and pool are very nice-all I can add is that we didn't want to leave and would love to return! … 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
"Casa Pineta" Authentic 4BR farmhouse community pool) near siena + florence
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. … see more

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