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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.

  • Showing 1-50 of 300+
Additional service fee may apply.
    Exceptional! 5.0/5
    (47 reviews)
    avg/night
    • 3 BR
    • 2 BA
    • Sleeps 8
    Apartment #1153926
    47
    Viewed 32 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 67 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 69 times in the last 48 hours
          Wonderful! 4.9/5
          (30 reviews)
          avg/night
          • 2 BR
          • 1 BA
          • Sleeps 6
          Apartment #1494217
          30
          Viewed 39 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 115 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 49 times in the last 48 hours
                Wonderful! 4.8/5
                (10 reviews)
                avg/night
                • 5 BR
                • 3 BA
                • Sleeps 11
                Castle #445224
                10
                Viewed 53 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 19 times in the last 48 hours
                    Exceptional! 5.0/5
                    (101 reviews)
                    avg/night
                    • 5 BR
                    • 6 BA
                    • Sleeps 12
                    Villa #420894
                    101
                    Viewed 56 times in the last 48 hours
                      • 4 BR
                      • 3 BA
                      • Sleeps 8
                      Multiple rentals House #411914
                      27
                      Viewed 92 times in the last 48 hours
                        Exceptional! 5.0/5
                        (18 reviews)
                        avg/night
                        • 5 BR
                        • 5 BA
                        • Sleeps 14
                        Villa #1654060
                        18
                        Viewed 39 times in the last 48 hours
                          Good! 3.8/5
                          (8 reviews)
                          avg/night
                          • 1 BR
                          • 1 BA
                          • Sleeps 3
                          Apartment #490040
                          8
                          Viewed 30 times in the last 48 hours
                            • 2 BR
                            • 2 BA
                            • Sleeps 4
                            Multiple rentals House #411914
                            6
                            Viewed 110 times in the last 48 hours
                              avg/night
                              • 4 BR
                              • 3 BA
                              • Sleeps 10
                              Multiple rentals Villa #1980452
                              4
                              Viewed 58 times in the last 48 hours
                                Exceptional! 5.0/5
                                (10 reviews)
                                avg/night
                                • 6 BR
                                • 4 BA
                                • Sleeps 11
                                Villa #444799vb
                                10
                                Viewed 31 times in the last 48 hours
                                  Wonderful! 4.9/5
                                  (8 reviews)
                                  avg/night
                                  • 8 BR
                                  • 9 BA
                                  • Sleeps 17
                                  Villa #70004
                                  8
                                  Viewed 16 times in the last 48 hours
                                    • 5 BR
                                    • 5 BA
                                    • Sleeps 10
                                    Multiple rentals Villa #411914
                                    8
                                    Viewed 36 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
                                        Excellent! 4.3/5
                                        (6 reviews)
                                        avg/night
                                        • 3 BR
                                        • 1 BA
                                        • Sleeps 6
                                        Multiple rentals Farmhouse #1980452
                                        6
                                        Viewed 66 times in the last 48 hours
                                          Wonderful! 4.8/5
                                          (29 reviews)
                                          avg/night
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 4
                                          Multiple rentals Chateau / Country House #475291
                                          29
                                          Viewed 31 times in the last 48 hours
                                            Exceptional! 5.0/5
                                            (6 reviews)
                                            avg/night
                                            • 4 BR
                                            • 3 BA
                                            • Sleeps 8
                                            Multiple rentals Villa #1683131
                                            6
                                            Viewed 12 times in the last 48 hours
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 2
                                              Multiple rentals Apartment #1728813
                                              3
                                              Viewed 29 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 16 times in the last 48 hours
                                                  • 2 BR
                                                  • 1 BA
                                                  • Separate Toilet
                                                  • Sleeps 4
                                                  Multiple rentals Apartment #1728813
                                                  1
                                                  Viewed 7 times in the last 48 hours
                                                    Exceptional! 5.0/5
                                                    (16 reviews)
                                                    avg/night
                                                    • 6 BR
                                                    • 6 BA
                                                    • Sleeps 13
                                                    Villa #1983677
                                                    16
                                                    Viewed 7 times in the last 48 hours
                                                      • 8 BR
                                                      • 4 BA
                                                      • Separate Toilet
                                                      • Sleeps 15
                                                      Multiple rentals Chateau / Country House #1728813
                                                      1
                                                      Viewed 15 times in the last 48 hours
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        Condo #6532070
                                                        0
                                                        Viewed 6 times in the last 48 hours
                                                          • 8 BR
                                                          • 6 BA
                                                          • Sleeps 18
                                                          Multiple rentals Villa #1980452
                                                          0
                                                          Viewed 49 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 53 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 11 times in the last 48 hours
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 5
                                                                  Multiple rentals Farmhouse #1728813
                                                                  0
                                                                  Viewed 14 times in the last 48 hours
                                                                    • 3 BR
                                                                    • 3 BA
                                                                    • Sleeps 6
                                                                    Villa #1151065
                                                                    0
                                                                    Viewed 15 times in the last 48 hours
                                                                      • 8 BR
                                                                      • 8 BA
                                                                      • Separate Toilet
                                                                      • Sleeps 16
                                                                      Villa #1150740
                                                                      0
                                                                      Viewed 5 times in the last 48 hours
                                                                        • 3 BR
                                                                        • 3 BA
                                                                        • Sleeps 8
                                                                        Villa #1150792
                                                                        3
                                                                        Viewed 5 times in the last 48 hours
                                                                          • 6 BR
                                                                          • 6 BA
                                                                          • Sleeps 16
                                                                          Villa #1544664
                                                                          0
                                                                          Viewed 7 times in the last 48 hours
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Sleeps 4
                                                                            Villa #1544793
                                                                            0
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 7
                                                                              Multiple rentals Farmhouse #1031717
                                                                              4
                                                                              Viewed 77 times in the last 48 hours
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 5
                                                                                Multiple rentals Farmhouse #1031717
                                                                                0
                                                                                Viewed 11 times in the last 48 hours
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 2
                                                                                  Multiple rentals Farmhouse #1031717
                                                                                  1
                                                                                  Viewed 17 times in the last 48 hours
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 4
                                                                                    Multiple rentals Farmhouse #1031717
                                                                                    0
                                                                                    Viewed 14 times in the last 48 hours
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 2
                                                                                      Multiple rentals Farmhouse #1031717
                                                                                      0
                                                                                      Viewed 7 times in the last 48 hours
                                                                                        Wonderful! 4.9/5
                                                                                        (9 reviews)
                                                                                        avg/night
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        Apartment #1627958
                                                                                        9
                                                                                        Viewed 26 times in the last 48 hours
                                                                                          avg/night
                                                                                          • 5 BR
                                                                                          • 5 BA
                                                                                          • Separate Toilet
                                                                                          • Sleeps 10
                                                                                          Villa #1097226
                                                                                          4
                                                                                          Viewed 107 times in the last 48 hours
                                                                                            Wonderful! 4.8/5
                                                                                            (12 reviews)
                                                                                            avg/night
                                                                                            • Studio
                                                                                            • 1 BA
                                                                                            • Sleeps 4
                                                                                            Apartment #1768734
                                                                                            12
                                                                                            Viewed 59 times in the last 48 hours
                                                                                              Exceptional! 5.0/5
                                                                                              (9 reviews)
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 4
                                                                                              Cottage #840201vb
                                                                                              9
                                                                                              Viewed 28 times in the last 48 hours
                                                                                                Excellent! 4.6/5
                                                                                                (11 reviews)
                                                                                                avg/night
                                                                                                • 6 BR
                                                                                                • 4 BA
                                                                                                • Sleeps 10
                                                                                                Villa #1410492
                                                                                                11
                                                                                                Viewed 8 times in the last 48 hours
                                                                                                  • 6 BR
                                                                                                  • 5 BA
                                                                                                  • Sleeps 11
                                                                                                  House #6700969
                                                                                                  0
                                                                                                  Viewed 16 times in the last 48 hours
                                                                                                    Exceptional! 5.0/5
                                                                                                    (8 reviews)
                                                                                                    avg/night
                                                                                                    • 2 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 5
                                                                                                    Apartment #578973vb
                                                                                                    8
                                                                                                    Viewed 10 times in the last 48 hours
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      Chateau / Country House #6610577
                                                                                                      20
                                                                                                      • 1 - 50 of 300+

                                                                                                      Siena Holiday Villas - Apartments in Siena (300+)

                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      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

                                                                                                      Perfect location and wonderful countryside

                                                                                                      5 of 5
                                                                                                      The drive up from d Arbia was beautiful and Anna and Francesca made us very welcome. It is a stunning location from which to explore some of Tuscany and after a day's sightseeing, it was lovely to return to with it's peace and tranquility. Clean and well maintained and very secure, comfortable beds and plenty of hanging space for clothes. Would recommend to friends and family.
                                                                                                      • Review Submitted: 07-Oct-2016
                                                                                                      • Date of Stay: Sep 2016