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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+
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    Exceptional! 5/5
    (47 reviews)
    avg/night
    • 3 BR
    • 2 BA
    • Sleeps 8
    Apartment #1153926
    47
    Viewed 43 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 57 times in the last 48 hours
        Wonderful! 4.9/5
        (9 reviews)
        avg/night
        • 1 BR
        • 1 BA
        • Sleeps 4
        Apartment #1627958
        9
        Viewed 20 times in the last 48 hours
          Exceptional! 5/5
          (4 reviews)
          avg/night
          • 5 BR
          • 5 BA
          • Separate Toilet
          • Sleeps 10
          Villa #1097226
          4
          Viewed 87 times in the last 48 hours
            • 2 BR
            • 2 BA
            • Sleeps 6
            Multiple rentals Apartment #6521915
            3
            Viewed 24 times in the last 48 hours
              Wonderful! 4.8/5
              (12 reviews)
              avg/night
              • Studio
              • 1 BA
              • Sleeps 4
              Apartment #1768734
              12
              Viewed 24 times in the last 48 hours
                Exceptional! 5/5
                (14 reviews)
                avg/night
                • 3 BR
                • 3 BA
                • Separate Toilet
                • Sleeps 4
                Multiple rentals Chateau / Country House #1898892
                14
                Viewed 30 times in the last 48 hours
                  Wonderful! 4.9/5
                  (13 reviews)
                  avg/night
                  • 2 BR
                  • 2 BA
                  • Sleeps 6
                  Apartment #13190
                  13
                  Viewed 13 times in the last 48 hours
                    Wonderful! 4.8/5
                    (10 reviews)
                    avg/night
                    • 5 BR
                    • 3 BA
                    • Sleeps 11
                    Castle #445224
                    10
                    Viewed 161 times in the last 48 hours
                      Exceptional! 5/5
                      (5 reviews)
                      avg/night
                      • 2 BR
                      • 2 BA
                      • Sleeps 4
                      Apartment #6066838
                      5
                      Viewed 14 times in the last 48 hours
                        Exceptional! 5/5
                        (29 reviews)
                        avg/night
                        • 6 BR
                        • 6 BA
                        • Separate Toilet
                        • Sleeps 12
                        Villa #1636667
                        29
                        Viewed 27 times in the last 48 hours
                          Wonderful! 4.9/5
                          (18 reviews)
                          avg/night
                          • 4 BR
                          • 4 BA
                          • Separate Toilet
                          • Sleeps 10
                          Multiple rentals Villa #1898892
                          18
                          Viewed 63 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 17 times in the last 48 hours
                              Wonderful! 4.9/5
                              (30 reviews)
                              avg/night
                              • 2 BR
                              • 1 BA
                              • Sleeps 6
                              Apartment #1494217
                              30
                              Viewed 19 times in the last 48 hours
                                Exceptional! 5/5
                                (102 reviews)
                                avg/night
                                • 5 BR
                                • 6 BA
                                • Sleeps 12
                                Villa #420894
                                102
                                Viewed 22 times in the last 48 hours
                                  Exceptional! 5/5
                                  (18 reviews)
                                  avg/night
                                  • 5 BR
                                  • 5 BA
                                  • Sleeps 14
                                  Villa #1654060
                                  18
                                  Viewed 45 times in the last 48 hours
                                    Wonderful! 4.8/5
                                    (4 reviews)
                                    avg/night
                                    • 4 BR
                                    • 3 BA
                                    • Sleeps 10
                                    Multiple rentals Villa #1980452
                                    4
                                    Viewed 20 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 50 times in the last 48 hours
                                        Exceptional! 5/5
                                        (10 reviews)
                                        avg/night
                                        • 6 BR
                                        • 4 BA
                                        • Sleeps 11
                                        Villa #444799vb
                                        10
                                        Viewed 32 times in the last 48 hours
                                          Wonderful! 4.8/5
                                          (30 reviews)
                                          avg/night
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 4
                                          Multiple rentals Chateau / Country House #475291
                                          30
                                          Viewed 18 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 21 times in the last 48 hours
                                              Exceptional! 5/5
                                              (6 reviews)
                                              avg/night
                                              • 4 BR
                                              • 3 BA
                                              • Sleeps 8
                                              Multiple rentals Villa #1683131
                                              6
                                              Viewed 13 times in the last 48 hours
                                                • 1 BR
                                                • 1 BA
                                                • Sleeps 2
                                                Multiple rentals Apartment #1728813
                                                3
                                                Viewed 12 times in the last 48 hours
                                                  • 2 BR
                                                  • 1 BA
                                                  • Separate Toilet
                                                  • Sleeps 4
                                                  Multiple rentals Apartment #1728813
                                                  1
                                                  Viewed 15 times in the last 48 hours
                                                    Exceptional! 5/5
                                                    (8 reviews)
                                                    avg/night
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    Multiple rentals Chateau / Country House #475291
                                                    8
                                                    Viewed 7 times in the last 48 hours
                                                      • 3 BR
                                                      • 3 BA
                                                      • Sleeps 6
                                                      Villa #1151065
                                                      Viewed 6 times in the last 48 hours
                                                        • 8 BR
                                                        • 4 BA
                                                        • Separate Toilet
                                                        • Sleeps 15
                                                        Multiple rentals Chateau / Country House #1728813
                                                        1
                                                        Viewed 35 times in the last 48 hours
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 4
                                                          Condo #6532070
                                                          Viewed 7 times in the last 48 hours
                                                            Exceptional! 5/5
                                                            (16 reviews)
                                                            avg/night
                                                            • 6 BR
                                                            • 6 BA
                                                            • Sleeps 13
                                                            Villa #1983677
                                                            16
                                                            Viewed 9 times in the last 48 hours
                                                              • 8 BR
                                                              • 6 BA
                                                              • Sleeps 18
                                                              Multiple rentals Villa #1980452
                                                              Viewed 32 times in the last 48 hours
                                                                Wonderful! 4.9/5
                                                                (8 reviews)
                                                                avg/night
                                                                • 5 BR
                                                                • 3 BA
                                                                • Sleeps 13
                                                                Multiple rentals Chateau / Country House #475291
                                                                8
                                                                Viewed 10 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
                                                                    Viewed 15 times in the last 48 hours
                                                                      Exceptional! 5/5
                                                                      (14 reviews)
                                                                      avg/night
                                                                      • 7 BR
                                                                      • 6 BA
                                                                      • Sleeps 14
                                                                      Villa #1983683
                                                                      14
                                                                      Viewed 6 times in the last 48 hours
                                                                        • 3 BR
                                                                        • 3 BA
                                                                        • Sleeps 8
                                                                        Villa #1150792
                                                                        3
                                                                          • 8 BR
                                                                          • 8 BA
                                                                          • Separate Toilet
                                                                          • Sleeps 16
                                                                          Villa #1150740
                                                                            • 6 BR
                                                                            • 6 BA
                                                                            • Sleeps 16
                                                                            Villa #1544664
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 4
                                                                              Villa #1544793
                                                                                Exceptional! 5/5
                                                                                (4 reviews)
                                                                                avg/night
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 7
                                                                                Multiple rentals Farmhouse #1031717
                                                                                4
                                                                                Viewed 50 times in the last 48 hours
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 2
                                                                                  Multiple rentals Farmhouse #1031717
                                                                                  1
                                                                                  Viewed 10 times in the last 48 hours
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 5
                                                                                    Multiple rentals Farmhouse #1031717
                                                                                    Viewed 6 times in the last 48 hours
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 4
                                                                                      Multiple rentals Farmhouse #1031717
                                                                                      Viewed 6 times in the last 48 hours
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 2
                                                                                        Multiple rentals Farmhouse #1031717
                                                                                          Wonderful! 4.8/5
                                                                                          (23 reviews)
                                                                                          avg/night
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 3
                                                                                          Apartment #1803159
                                                                                          23
                                                                                          Viewed 27 times in the last 48 hours
                                                                                            Excellent! 4.7/5
                                                                                            (6 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 4
                                                                                            Apartment #1870265
                                                                                            6
                                                                                            Viewed 10 times in the last 48 hours
                                                                                              avg/night
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 9
                                                                                              Apartment #6368871
                                                                                              Viewed 8 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (12 reviews)
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 5
                                                                                                Farmhouse #6392839
                                                                                                12
                                                                                                Viewed 25 times in the last 48 hours
                                                                                                  • 2 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  Multiple rentals Apartment #6521915
                                                                                                  Viewed 19 times in the last 48 hours
                                                                                                    • 2 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 4
                                                                                                    Multiple rentals House #411914
                                                                                                    6
                                                                                                    Viewed 16 times in the last 48 hours
                                                                                                      Exceptional! 5/5
                                                                                                      (9 reviews)
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 4
                                                                                                      Cottage #840201vb
                                                                                                      9
                                                                                                      Viewed 9 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Siena Holiday Villas - Apartments in Siena (300+)

                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      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

                                                                                                      Beautiful accommodations and view, amazing staff!!

                                                                                                      5 of 5
                                                                                                      Four of us stayed in one of the two bedroom apartments and it was beautiful, very big, spotlessly clean, and the view and property was beyond breathtaking. The staff were really friendly and more than accomodating!! Their own wine is absolutely fantastic, which they sell at reception for next to nothing! We will abolutely return here, we give it a 5+ Star It was super close to Sienna, which is amazing in itself, fantastic shopping and a beautiful walled city. Really something to behold. Plus all the amenities, grocery store etc
                                                                                                      • Review Submitted: 06-Oct-2016
                                                                                                      • Date of Stay: Sep 2016