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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.

    • 2 BR
    • 1 BA
    • Sleeps 4
    Apartment #4216056
    3
    Viewed 19 times in the last 48 hours
      Wonderful! 4.8/5
      (6 reviews)
      avg/night
      • 5 BR
      • 5 BA
      • Separate Toilet
      • Sleeps 10
      Villa #1097226
      6
      Viewed 49 times in the last 48 hours
        Wonderful! 4.9/5
        (17 reviews)
        avg/night
        • 6 BR
        • 5 BA
        • Separate Toilets
        • Sleeps 14
        Villa #1617223
        17
        Viewed 65 times in the last 48 hours
          Exceptional! 5/5
          (18 reviews)
          avg/night
          • 3 BR
          • 3 BA
          • Separate Toilet
          • Sleeps 4
          Multiple rentals Chateau / Country House #1898892
          18
          Viewed 19 times in the last 48 hours
            Exceptional! 5/5
            (33 reviews)
            avg/night
            • 6 BR
            • 6 BA
            • Separate Toilet
            • Sleeps 12
            Villa #1636667
            33
            Viewed 57 times in the last 48 hours
              Wonderful! 4.9/5
              (17 reviews)
              avg/night
              • 2 BR
              • 2 BA
              • Sleeps 6
              Apartment #13190
              17
              Viewed 25 times in the last 48 hours
                Wonderful! 4.8/5
                (14 reviews)
                avg/night
                • 1 BR
                • 1 BA
                • Sleeps 4
                Apartment #1627958
                14
                Viewed 14 times in the last 48 hours
                  Exceptional! 5/5
                  (26 reviews)
                  avg/night
                  • 4 BR
                  • 4 BA
                  • Separate Toilet
                  • Sleeps 10
                  Multiple rentals Villa #1898892
                  26
                  Viewed 17 times in the last 48 hours
                    Wonderful! 4.9/5
                    (12 reviews)
                    avg/night
                    • 2 BR
                    • 1 BA
                    • Sleeps 4
                    Apartment #1198165a
                    12
                    Viewed 15 times in the last 48 hours
                      Wonderful! 4.8/5
                      (31 reviews)
                      avg/night
                      • 1 BR
                      • 1 BA
                      • Sleeps 3
                      Apartment #1803159
                      31
                      Viewed 27 times in the last 48 hours
                        Wonderful! 4.8/5
                        (9 reviews)
                        avg/night
                        • 2 BR
                        • 1 BA
                        • Sleeps 4
                        Apartment #1870265
                        9
                        Viewed 6 times in the last 48 hours
                          Wonderful! 4.8/5
                          (13 reviews)
                          avg/night
                          • Studio
                          • 1 BA
                          • Sleeps 4
                          Apartment #1768734
                          13
                          Viewed 6 times in the last 48 hours
                            Wonderful! 4.9/5
                            (18 reviews)
                            avg/night
                            • 2 BR
                            • 2 BA
                            • Sleeps 5
                            Farmhouse #6392839
                            18
                            Viewed 9 times in the last 48 hours
                              Excellent! 4.6/5
                              (5 reviews)
                              avg/night
                              • 2 BR
                              • 2 BA
                              • Sleeps 6
                              Multiple rentals Apartment #6521915
                              5
                              Viewed 10 times in the last 48 hours
                                Exceptional! 5/5
                                (23 reviews)
                                avg/night
                                • 5 BR
                                • 5 BA
                                • Sleeps 14
                                Villa #1654060
                                23
                                Viewed 28 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 14 times in the last 48 hours
                                    avg/night
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 5
                                    House #6024561
                                    4
                                    Viewed 24 times in the last 48 hours
                                      • 4 BR
                                      • 3 BA
                                      • Sleeps 8
                                      Multiple rentals House #411914
                                      32
                                      Viewed 49 times in the last 48 hours
                                        Exceptional! 5/5
                                        (13 reviews)
                                        avg/night
                                        • 2 BR
                                        • 2 BA
                                        • Sleeps 4
                                        Cottage #840201vb
                                        13
                                        Viewed 8 times in the last 48 hours
                                          • 2 BR
                                          • 2 BA
                                          • Sleeps 4
                                          Multiple rentals House #411914
                                          8
                                          Viewed 14 times in the last 48 hours
                                            Exceptional! 5/5
                                            (25 reviews)
                                            avg/night
                                            • 2 BR
                                            • 2 BA
                                            • Sleeps 5
                                            Apartment #1835979
                                            25
                                            Viewed 12 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (9 reviews)
                                              avg/night
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 3
                                              Apartment #6745717
                                              9
                                              Viewed 16 times in the last 48 hours
                                                Wonderful! 4.8/5
                                                (6 reviews)
                                                avg/night
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 5
                                                Apartment #490856vb
                                                6
                                                  Exceptional! 5/5
                                                  (10 reviews)
                                                  avg/night
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 7
                                                  Villa #6833125
                                                  10
                                                  Viewed 26 times in the last 48 hours
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    Multiple rentals Apartment #455240
                                                    1
                                                    Viewed 19 times in the last 48 hours
                                                      Good! 3.7/5
                                                      (10 reviews)
                                                      avg/night
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      Apartment #6484784
                                                      10
                                                      Viewed 9 times in the last 48 hours
                                                        Wonderful! 4.9/5
                                                        (23 reviews)
                                                        avg/night
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 5
                                                        Villa #446972
                                                        23
                                                        Viewed 12 times in the last 48 hours
                                                          Exceptional! 5/5
                                                          (11 reviews)
                                                          avg/night
                                                          • 6 BR
                                                          • 4 BA
                                                          • Sleeps 11
                                                          Villa #444799vb
                                                          11
                                                          Viewed 21 times in the last 48 hours
                                                            Exceptional! 5/5
                                                            (102 reviews)
                                                            avg/night
                                                            • 5 BR
                                                            • 6 BA
                                                            • Sleeps 12
                                                            Villa #420894
                                                            102
                                                            Viewed 20 times in the last 48 hours
                                                              Excellent! 4.5/5
                                                              (8 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 1 BA
                                                              • Sleeps 6
                                                              Multiple rentals Farmhouse #1980452
                                                              8
                                                              Viewed 8 times in the last 48 hours
                                                                avg/night
                                                                • 4 BR
                                                                • 3 BA
                                                                • Sleeps 10
                                                                Multiple rentals Villa #1980452
                                                                4
                                                                Viewed 10 times in the last 48 hours
                                                                  Exceptional! 5/5
                                                                  (9 reviews)
                                                                  avg/night
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 4
                                                                  Multiple rentals Chateau / Country House #475291
                                                                  9
                                                                  Viewed 7 times in the last 48 hours
                                                                    Wonderful! 4.8/5
                                                                    (32 reviews)
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 1 BA
                                                                    • Sleeps 5
                                                                    Multiple rentals Chateau / Country House #475291
                                                                    32
                                                                    Viewed 16 times in the last 48 hours
                                                                      Wonderful! 4.8/5
                                                                      (31 reviews)
                                                                      avg/night
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      Multiple rentals Chateau / Country House #475291
                                                                      31
                                                                      Viewed 16 times in the last 48 hours
                                                                        Excellent! 4.7/5
                                                                        (9 reviews)
                                                                        avg/night
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 4
                                                                        Multiple rentals Apartment #1683131
                                                                        9
                                                                        Viewed 6 times in the last 48 hours
                                                                          • 3 BR
                                                                          • 3 BA
                                                                          • Sleeps 6
                                                                          Villa #1151065
                                                                          Viewed 11 times in the last 48 hours
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Sleeps 4
                                                                            Villa #1544793
                                                                            Viewed 8 times in the last 48 hours
                                                                              Exceptional! 5/5
                                                                              (7 reviews)
                                                                              avg/night
                                                                              • 4 BR
                                                                              • 3 BA
                                                                              • Sleeps 8
                                                                              Multiple rentals Villa #1683131
                                                                              7
                                                                              Viewed 7 times in the last 48 hours
                                                                                • 8 BR
                                                                                • 6 BA
                                                                                • Sleeps 18
                                                                                Multiple rentals Villa #1980452
                                                                                Viewed 40 times in the last 48 hours
                                                                                  • 6 BR
                                                                                  • 6 BA
                                                                                  • Sleeps 13
                                                                                  Villa #1983677
                                                                                  16
                                                                                    Wonderful! 4.9/5
                                                                                    (8 reviews)
                                                                                    avg/night
                                                                                    • 5 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 13
                                                                                    Multiple rentals Chateau / Country House #475291
                                                                                    8
                                                                                    Viewed 6 times in the last 48 hours
                                                                                      Exceptional! 5/5
                                                                                      (14 reviews)
                                                                                      avg/night
                                                                                      • 7 BR
                                                                                      • 6 BA
                                                                                      • Sleeps 14
                                                                                      Villa #1983683
                                                                                      14
                                                                                      Viewed 5 times in the last 48 hours
                                                                                        • 3 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 8
                                                                                        Villa #1150792
                                                                                        3
                                                                                          • 6 BR
                                                                                          • 6 BA
                                                                                          • Sleeps 16
                                                                                          Villa #1544664
                                                                                            • 8 BR
                                                                                            • 8 BA
                                                                                            • Separate Toilet
                                                                                            • Sleeps 16
                                                                                            Villa #1150740
                                                                                            Viewed 8 times in the last 48 hours
                                                                                              Wonderful! 4.9/5
                                                                                              (34 reviews)
                                                                                              avg/night
                                                                                              • 3 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 8
                                                                                              Farmhouse #435593vb
                                                                                              34
                                                                                              Viewed 15 times in the last 48 hours
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 1
                                                                                                Apartment #6790484
                                                                                                  • 4 BR
                                                                                                  • 2 BA
                                                                                                  • Separate Toilet
                                                                                                  • Sleeps 8
                                                                                                  Apartment #6899241
                                                                                                  4
                                                                                                  Viewed 12 times in the last 48 hours
                                                                                                    • 2 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 4
                                                                                                    Multiple rentals Apartment #6521915
                                                                                                    3
                                                                                                    Viewed 6 times in the last 48 hours
                                                                                                      Exceptional! 5/5
                                                                                                      (25 reviews)
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 4
                                                                                                      Apartment #170163vb
                                                                                                      25

                                                                                                      Siena Holiday Villas - Apartments in Siena (300+)

                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      Fantastic Villa is stunning countryside

                                                                                                      5 of 5
                                                                                                      We spent 7 nights at Legnaia at Borgo la Chiusa in July 2017. Our family of four, 2 adults and 2 children aged 12 and 15, all had a great time. The villa is immaculately presented both inside and out with outstanding facilities, especially the outdoor seating/dining areas and the swimming pool. Our host Simone met us at the villa on arrival and explained everything for us and was available throughout for any issues or advice. The town of Siena is only a 10min drive and both Florence and Pisa are about an hours drive away so perfectly situated. We wouldn't hesitate to return.
                                                                                                      • Review Submitted: Jul 21, 2017
                                                                                                      • Date of Stay: Jul 2017

                                                                                                      GORGEOUS HOUSE, PERFECT FOR FAMILY HOLIDAY

                                                                                                      4 of 5
                                                                                                      We all loved this house, loads of room for our extended family, well equipped kitchen for the cooks, gorgeous swimming pool and large terrace for relaxing, perfect covered area for our family meals. The location with magnificent views of Siena and the surrounding countryside was amazing. Only negative was that the internet didn't function at all for most of our stay which was a problem for members of the family who needed to do some urgent work
                                                                                                      • Review Submitted: Jun 25, 2017
                                                                                                      • Date of Stay: Jun 2017