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Holidaymakers searching for holiday rentals in Siena also enquired about villas in Cortona, apartments in Lucca and apartments in Radicondoli

Make a holiday villa in Siena your home away from home

Siena is a beautiful Tuscan hill city that has preserved much of its medieval character. It’s there in the quaint alleyways, ancient churches, towers and the sprawling main piazza known as Il Campo, famous for the Palio horse race that’s held twice a year. In fact, Siena looks a lot like it did way back in the 14th century. Surrounding the city is a lush countryside of olive groves and vineyards, both of which have contributed greatly to Siena’s wealth.

Visitors to this part of Tuscany need comfortable and lovingly furnished properties to stay in, and HomeAway has some exceptional Siena holiday villas to that end. With prices starting from £450 per week they represent excellent value for money. Those with a passion for the outdoors need look no further as these holiday properties are located in the fabulous countryside close to the historic city. Siena holiday apartments within the medieval metropolis are also available and benefit from close proximity to the major sites. If the taste for medieval towns doesn't stop with Siena, spend some time in nearby Montepulciano where more beautiful holiday rentals are available.

Things to do

-Churches: Siena’s churches range from simple, stone structures such as the Church of San Francesco to the grand and imposing 15th-century cathedral. One of Siena's religious highlights is Pieve a Castello, a rural church built in the 11th century, although historians believe its origins are much older.

-Historic monuments: Siena’s stone cityscape includes numerous castles and the 100-metre-high Torre del Mangia. Built in the 14th century this slender structure has dominated the Palazzo Pubblico for almost 700 years. Visitors can also explore the magnificent 13th-century Montalcino Castle and the red-brick Medicea Fortress. This huge defensive stronghold also houses an open-air theatre.

-Gardens: Visitors with Siena holiday apartments can unwind in the serene settings of its gardens. Orto Botanico is a large, green expanse in the heart of the city with plant species from many different countries. Among the ilex and oak trees of Chianti Sculpture Park are sculptures from famous artists from five continents.

-Festivals: Siena's Palio attracts visitors from all over the world. This colourful and spectacular festival is held twice a year and sees the Piazza del Campo packed with dirt for bareback horse races. They are accompanied by pageantry and parties including feasts, parades, flag waving and solemn ceremonies. These events date back to medieval times, and due to their popularity, it is advised to book accommodation well in advance.

Weather in Siena

Siena is a good year-round destination with warm, mild weather for most of the time. The summers can be hot with July temperatures peaking at around 33°C. Winters are mild with average daily temperatures of around 10°C. Although Siena receives plenty of sunshine, the skies during winter are often overcast.

Travel to Siena

Travellers with holiday villas in Siena can fly into airports at Pisa, Florence, Rome and Bologna and connect to the medieval city by car or rail. The railway station is outside of Siena so some visitors may find it more convenient to come by bus. There are many SITA bus services throughout the region. Hire cars are a popular means to get around, although the centre of Siena is only accessible by foot.

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  • Showing 1-50 of 300+
Additional service fee may apply.
    Wonderful! 4.9/5
    (29 reviews)
    avg/night
    • 2 BR
    • 1 BA
    • Sleeps 6
    Apartment #1494217
    29
    Viewed 25 times in the last 48 hours
      Wonderful! 4.9/5
      (15 reviews)
      avg/night
      • 6 BR
      • 5 BA
      • Separate Toilets
      • Sleeps 14
      Villa #1617223
      15
      Viewed 26 times in the last 48 hours
        Exceptional! 5.0/5
        (29 reviews)
        avg/night
        • 6 BR
        • 6 BA
        • Separate Toilet
        • Sleeps 12
        Villa #1636667
        29
        Viewed 11 times in the last 48 hours
          Wonderful! 4.8/5
          (9 reviews)
          avg/night
          • 5 BR
          • 3 BA
          • Sleeps 11
          Castle #445224
          9
          Viewed 14 times in the last 48 hours
            Excellent! 4.7/5
            (9 reviews)
            avg/night
            • 4 BR
            • 3 BA
            • Sleeps 12
            Multiple rentals Villa #1980452
            9
            Viewed 13 times in the last 48 hours
              Exceptional! 5.0/5
              (17 reviews)
              avg/night
              • 4 BR
              • 4 BA
              • Separate Toilet
              • Sleeps 10
              Multiple rentals Villa #1898892
              17
              Viewed 9 times in the last 48 hours
                Exceptional! 5.0/5
                (100 reviews)
                avg/night
                • 5 BR
                • 6 BA
                • Sleeps 12
                Villa #420894
                100
                Viewed 16 times in the last 48 hours
                  Exceptional! 5.0/5
                  (14 reviews)
                  avg/night
                  • 3 BR
                  • 3 BA
                  • Separate Toilet
                  • Sleeps 4
                  Multiple rentals Chateau / Country House #1898892
                  14
                  Viewed 14 times in the last 48 hours
                    Exceptional! 5.0/5
                    (18 reviews)
                    avg/night
                    • 5 BR
                    • 5 BA
                    • Sleeps 14
                    Villa #1654060
                    18
                    Viewed 5 times in the last 48 hours
                      Good! 3.8/5
                      (8 reviews)
                      avg/night
                      • 1 BR
                      • 1 BA
                      • Sleeps 3
                      Apartment #490040
                      8
                      Viewed 22 times in the last 48 hours
                        Excellent! 4.7/5
                        (7 reviews)
                        avg/night
                        • 2 BR
                        • 2 BA
                        • Sleeps 4
                        Multiple rentals Apartment #1683131
                        7
                        Viewed 6 times in the last 48 hours
                          avg/night
                          • 4 BR
                          • 3 BA
                          • Sleeps 10
                          Multiple rentals Villa #1980452
                          4
                          Viewed 7 times in the last 48 hours
                            Exceptional! 5.0/5
                            (10 reviews)
                            avg/night
                            • 6 BR
                            • 4 BA
                            • Sleeps 11
                            Villa #444799vb
                            10
                            Viewed 7 times in the last 48 hours
                              • 4 BR
                              • 3 BA
                              • Sleeps 8
                              Multiple rentals House #411914
                              27
                              Viewed 73 times in the last 48 hours
                                • 2 BR
                                • 2 BA
                                • Sleeps 4
                                Multiple rentals House #411914
                                5
                                Viewed 35 times in the last 48 hours
                                  Excellent! 4.3/5
                                  (6 reviews)
                                  avg/night
                                  • 3 BR
                                  • 1 BA
                                  • Sleeps 6
                                  Multiple rentals Farmhouse #1980452
                                  6
                                  Viewed 19 times in the last 48 hours
                                    • 4 BR
                                    • 4 BA
                                    • Sleeps 8
                                    Apartment #6050425
                                    11
                                      Wonderful! 4.9/5
                                      (8 reviews)
                                      avg/night
                                      • 8 BR
                                      • 9 BA
                                      • Sleeps 17
                                      Villa #70004
                                      8
                                      Viewed 39 times in the last 48 hours
                                        • 5 BR
                                        • 5 BA
                                        • Sleeps 10
                                        Multiple rentals Villa #411914
                                        8
                                        Viewed 12 times in the last 48 hours
                                          • 4 BR
                                          • 3 BA
                                          • Sleeps 8
                                          Multiple rentals Villa #1683131
                                          6
                                            Wonderful! 4.8/5
                                            (29 reviews)
                                            avg/night
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 4
                                            Multiple rentals Chateau / Country House #475291
                                            29
                                            Viewed 10 times in the last 48 hours
                                              • 6 BR
                                              • 6 BA
                                              • Sleeps 13
                                              Villa #1983677
                                              16
                                                • 1 BR
                                                • 1 BA
                                                • Sleeps 2
                                                Multiple rentals Apartment #1728813
                                                3
                                                Viewed 9 times in the last 48 hours
                                                  Exceptional! 5.0/5
                                                  (8 reviews)
                                                  avg/night
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 4
                                                  Multiple rentals Chateau / Country House #475291
                                                  8
                                                  Viewed 6 times in the last 48 hours
                                                    • 2 BR
                                                    • 1 BA
                                                    • Separate Toilet
                                                    • Sleeps 4
                                                    Multiple rentals Apartment #1728813
                                                    1
                                                    Viewed 6 times in the last 48 hours
                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 4
                                                      Condo #6532070
                                                        • 8 BR
                                                        • 4 BA
                                                        • Separate Toilet
                                                        • Sleeps 15
                                                        Multiple rentals Chateau / Country House #1728813
                                                        1
                                                        Viewed 15 times in the last 48 hours
                                                          • 7 BR
                                                          • 6 BA
                                                          • Sleeps 14
                                                          Villa #1983683
                                                          14
                                                            Wonderful! 4.9/5
                                                            (8 reviews)
                                                            avg/night
                                                            • 5 BR
                                                            • 3 BA
                                                            • Sleeps 13
                                                            Multiple rentals Chateau / Country House #475291
                                                            8
                                                            Viewed 13 times in the last 48 hours
                                                              Wonderful! 4.8/5
                                                              (30 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 1 BA
                                                              • Sleeps 5
                                                              Multiple rentals Chateau / Country House #475291
                                                              30
                                                              Viewed 10 times in the last 48 hours
                                                                • 3 BR
                                                                • 2 BA
                                                                • Sleeps 5
                                                                Multiple rentals Farmhouse #1728813
                                                                  • 3 BR
                                                                  • 3 BA
                                                                  • Sleeps 6
                                                                  Villa #1151065
                                                                  Viewed 9 times in the last 48 hours
                                                                    • 8 BR
                                                                    • 8 BA
                                                                    • Separate Toilet
                                                                    • Sleeps 16
                                                                    Villa #1150740
                                                                      • 6 BR
                                                                      • 6 BA
                                                                      • Sleeps 16
                                                                      Villa #1544664
                                                                        • 3 BR
                                                                        • 3 BA
                                                                        • Sleeps 8
                                                                        Villa #1150792
                                                                        3
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 4
                                                                          Villa #1544793
                                                                            Wonderful! 4.8/5
                                                                            (14 reviews)
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 2 BA
                                                                            • Sleeps 10
                                                                            Chateau / Country House #1356264
                                                                            14
                                                                            Viewed 10 times in the last 48 hours
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 7
                                                                              Multiple rentals Farmhouse #1031717
                                                                              4
                                                                              Viewed 15 times in the last 48 hours
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 5
                                                                                Multiple rentals Farmhouse #1031717
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 2
                                                                                  Multiple rentals Farmhouse #1031717
                                                                                  1
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 4
                                                                                    Multiple rentals Farmhouse #1031717
                                                                                    Viewed 5 times in the last 48 hours
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 2
                                                                                      Multiple rentals Farmhouse #1031717
                                                                                        Exceptional! 5.0/5
                                                                                        (9 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 4
                                                                                        Cottage #840201vb
                                                                                        9
                                                                                        Viewed 20 times in the last 48 hours
                                                                                          Excellent! 4.6/5
                                                                                          (11 reviews)
                                                                                          avg/night
                                                                                          • 6 BR
                                                                                          • 4 BA
                                                                                          • Sleeps 10
                                                                                          Villa #1410492
                                                                                          11
                                                                                          Viewed 7 times in the last 48 hours
                                                                                            • 5 BR
                                                                                            • 3 BA
                                                                                            • Separate Toilet
                                                                                            • Sleeps 12
                                                                                            Villa #1272960
                                                                                            1
                                                                                              • 6 BR
                                                                                              • 5 BA
                                                                                              • Sleeps 11
                                                                                              House #6700969
                                                                                              Viewed 22 times in the last 48 hours
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 3
                                                                                                Multiple rentals Chateau / Country House #445045
                                                                                                10
                                                                                                  Excellent! 4.7/5
                                                                                                  (12 reviews)
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 5
                                                                                                  Multiple rentals Farmhouse #445045
                                                                                                  12
                                                                                                  Viewed 11 times in the last 48 hours
                                                                                                    • 2 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 4
                                                                                                    Multiple rentals Apartment #445045
                                                                                                    3
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 2
                                                                                                      Multiple rentals Farmhouse #6623303
                                                                                                      • 1 - 50 of 300+

                                                                                                      Siena Holiday Villas - Apartments in Siena (300+)

                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      Explore Siena from this fabulous hillside oasis

                                                                                                      5 of 5
                                                                                                      Santa Chiara was exactly as described, well equipped, the perfect location from which to explore Siena - just 15 minutes walk to the Piazza del Campo, and a little further to the bus station. The spectacular pool and accommodation were wonderful to retreat to at the end of a full day, or a lovely tranquil place to relax or take a walk through the olive groves, while enjoying views of the ancient city and its walls. It is the best of both worlds, having close pedestrian access to Siena and the peace and quiet of the countryside. Anna and her daughter, Claudia, were very welcoming and helpful. Be sure to take Claudia's free tour of the Duomo and city, and learn more about the art, history and customs of Sienna. We can't imagine a better place to stay and hope to return one day.
                                                                                                      • Review Submitted: 30-Oct-2016
                                                                                                      • Date of Stay: Sep 2016

                                                                                                      Absolutely Fantastic!!

                                                                                                      5 of 5
                                                                                                      I looked for months for a villa to rent and was so happy when I came across Borgo La Chuisa and the Fienile unit. Simone (the manager) was so easy to deal with and gave me so much information before I committed to rent. This was a special trip for me, my daughter, my niece, and friend. Upon arriving, we were in awe driving up the road to this beautiful property. The girls could not believe this was where we were staying. We each had our own room with our own bathroom. And the views were so stunning. The whole place was spotless and just beautiful. I had arranged for a welcome dinner from Simone prior to arriving and Francesca, the owner of the property, cooked for us our first night and it was absolutely delicious. We could not believe we were not in a restaurant. The food, the wine, the dessert, were all amazing. Staying here was the highlight of our whole Italy trip and we all can't wait to come back some day! Thank you Simone and Francesca. You made my birthday trip Perfect!!
                                                                                                      • Review Submitted: 25-Oct-2016
                                                                                                      • Date of Stay: May 2016

                                                                                                      Fantastic week

                                                                                                      5 of 5
                                                                                                      House was great, had all that we needed, jacopo and Fabio most attentive, lots of hot water for showers, great fun with the wood fired hot tub ! Would highly recommend it, we were a group of twelve, there's plenty of spaces for quiet areas and roudy times, I would hope to be back in a year or two. Thanks jacopo and Fabio for the use of your wonderful house/ villa.
                                                                                                      • Review Submitted: 08-Oct-2016
                                                                                                      • Date of Stay: Oct 2016