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Make a holiday rental house or villa in Chianti Senese, Tuscany, Italy your home away from home

The famous Italian region of Chianti, Tuscany, is a rural region lying between Firenze and Siena. Chianti, world renowned for its wine, is divided into two sections, Chianti Fiorentino and Chianti Senese, the heart of Tuscany. Chianti Senese is a beautiful region around Siena, with landscapes ranging from lush rolling hills and wide plains to the soaring hills of Radda and Gaiole, making Chianti Senese ideal for cycling holidays.

Things to do on holiday to Chianti Senese, Italy

Walking, horse riding and cycling holidays keep the holiday houses and rental villas of Chianti Senese busy all year round. The stunning, varied and unspoilt landscape of Chianti Senese lends itself perfectly for relaxing strolls and slightly more strenuous rides. However, when you return from a hard day touring the region, there is nothing better than relaxing in a luxury villa in Chianti Senese with a glass or two of Chianti wine, straight from the surrounding vineyards. This is predominantly a rural region, and agrotourism has taken off in a large way. Farm holidays to Chianti Senese are very popular, and there is some magnificent local produce to cook with in a self catering holiday house. As a result, there are now a range of expert cooking courses available when you stay in holiday accommodation in Chianti Senese.

The rivers of Ombrone, Ambra, Bozzone, Gena and Pese cross Chianti Senese giving walkers and hikers a ready made set of routes, and fabulous places to use a fishing rod. A holiday rental in Chianti Senese allows not only the exploration of some of Tuscany’s best loved cities like Siena and Florence, but they are also within an hour of the famous Tuscan beaches to the west.

Wine testing and vineyard tours are of course hugely popular and hugely interesting options from a holiday rental in Chianti, and there are plenty on offer, often offering tasting lessons.

Chianti Senese has a history lasting back to before 2,000BC, which is evident in the numerous Etruscan and medieval sites, castles, villages, churches and rural villas. The Castle of Brolio is possible the most picturesque example in the area, set in a sublime rural setting, well worth visiting from any of the self catering villas in Chianti Senese.

Weather in Chianti Senese, Italy

Summers in Chianti Senese are blissfully hot, with daily averages in July and August soaring above 30°C on most days. Winters are cold though, but this does not stop a holiday villa in Chianti Senese being a great rural base for family holidays exploring the cities of Siena and Florence.

Travel to Chianti Senese, Italy

Florence Airport is the closest to the holiday rental villas of Chianti Senese, being within 45 minutes. There are many excellent options for cheap flights to Chianti Senese from across the UK.

  • Showing 1-50 of 300+
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    Excellent! 4.6/5
    (9 reviews)
    avg/night
    • 3 BR
    • 3 BA
    • Sleeps 6
    Farmhouse #8461
    9
    Viewed 48 times in the last 48 hours
      Exceptional! 5/5
      (60 reviews)
      avg/night
      • 2 BR
      • 1 BA
      • Sleeps 4
      Multiple rentals Apartment #6029171
      60
      Viewed 38 times in the last 48 hours
        Wonderful! 4.9/5
        (73 reviews)
        avg/night
        • 2 BR
        • 3 BA
        • Separate Toilet
        • Sleeps 5
        Multiple rentals Cottage #6029171
        73
        Viewed 78 times in the last 48 hours
          Wonderful! 4.8/5
          (9 reviews)
          avg/night
          • 4 BR
          • 3 BA
          • Separate Toilet
          • Sleeps 6
          Villa #64607vb
          9
          Viewed 14 times in the last 48 hours
            • 1 BR
            • 1 BA
            • Sleeps 4
            Multiple rentals Apartment #38930
            3
            Viewed 23 times in the last 48 hours
              Exceptional! 5/5
              (4 reviews)
              avg/night
              • 2 BR
              • 1 BA
              • Separate Toilet
              • Sleeps 6
              Multiple rentals House #38930
              4
              Viewed 14 times in the last 48 hours
                Wonderful! 4.8/5
                (19 reviews)
                avg/night
                • 2 BR
                • 1 BA
                • Sleeps 4
                Multiple rentals Villa #64960
                19
                Viewed 20 times in the last 48 hours
                  Exceptional! 5/5
                  (51 reviews)
                  avg/night
                  • 3 BR
                  • 3 BA
                  • Sleeps 6
                  Multiple rentals Villa #64960
                  51
                  Viewed 10 times in the last 48 hours
                    • 2 BR
                    • 1 BA
                    • Sleeps 4
                    Multiple rentals Villa #79371
                    2
                    Viewed 12 times in the last 48 hours
                      • 2 BR
                      • 2 BA
                      • Sleeps 5
                      Multiple rentals Villa #79371
                      Viewed 6 times in the last 48 hours
                        • 2 BR
                        • 1 BA
                        • Sleeps 4
                        Multiple rentals Villa #79371
                        Viewed 7 times in the last 48 hours
                          • 1 BR
                          • 1 BA
                          • Sleeps 3
                          Multiple rentals Apartment #79371
                          1
                            • 1 BR
                            • 1 BA
                            • Sleeps 3
                            Multiple rentals Villa #79371
                              Exceptional! 5/5
                              (86 reviews)
                              avg/night
                              • 3 BR
                              • 3 BA
                              • Sleeps 6
                              Villa #95620
                              86
                              Viewed 25 times in the last 48 hours
                                • 1 BR
                                • 1 BA
                                • Sleeps 3
                                Multiple rentals Apartment #401530
                                15
                                  Wonderful! 4.8/5
                                  (25 reviews)
                                  avg/night
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 7
                                  Multiple rentals Villa #401530
                                  25
                                  Viewed 19 times in the last 48 hours
                                    • 5 BR
                                    • 4 BA
                                    • Sleeps 14
                                    Multiple rentals Villa #401530
                                    6
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 4
                                      Multiple rentals Apartment #401530
                                      8
                                      Viewed 7 times in the last 48 hours
                                        Wonderful! 4.9/5
                                        (22 reviews)
                                        avg/night
                                        • 3 BR
                                        • 3 BA
                                        • Sleeps 6
                                        Villa #421433
                                        22
                                        Viewed 30 times in the last 48 hours
                                          Exceptional! 5/5
                                          (44 reviews)
                                          avg/night
                                          • 2 BR
                                          • 2 BA
                                          • Sleeps 4
                                          Apartment #433025
                                          44
                                          Viewed 10 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (30 reviews)
                                            avg/night
                                            • 5 BR
                                            • 5 BA
                                            • Sleeps 10
                                            Villa #275267
                                            30
                                            Viewed 34 times in the last 48 hours
                                              Excellent! 4.7/5
                                              (12 reviews)
                                              avg/night
                                              • 7 BR
                                              • 7 BA
                                              • Separate Toilets
                                              • Sleeps 15
                                              Farmhouse #443694vb
                                              12
                                              Viewed 13 times in the last 48 hours
                                                Exceptional! 5/5
                                                (13 reviews)
                                                avg/night
                                                • 7 BR
                                                • 4 BA
                                                • Sleeps 14
                                                Multiple rentals Farmhouse #1140076
                                                13
                                                Viewed 5 times in the last 48 hours
                                                  Exceptional! 5/5
                                                  (12 reviews)
                                                  avg/night
                                                  • 4 BR
                                                  • 2 BA
                                                  • Sleeps 8
                                                  Multiple rentals Farmhouse #1140076
                                                  12
                                                  Viewed 12 times in the last 48 hours
                                                    • 9 BR
                                                    • 5 BA
                                                    • Sleeps 18
                                                    Multiple rentals Villa #1140076
                                                    17
                                                    Viewed 11 times in the last 48 hours
                                                      Wonderful! 4.9/5
                                                      (8 reviews)
                                                      avg/night
                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 5
                                                      Multiple rentals Farmhouse #1140076
                                                      8
                                                      Viewed 16 times in the last 48 hours
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        Multiple rentals Farmhouse #1140076
                                                        8
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          Villa #1150760
                                                            • 7 BR
                                                            • 6 BA
                                                            • Separate Toilet
                                                            • Sleeps 13
                                                            Villa #1150681
                                                              Wonderful! 4.9/5
                                                              (32 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 3 BA
                                                              • Separate Toilet
                                                              • Sleeps 7
                                                              Villa #709879vb
                                                              32
                                                              Viewed 50 times in the last 48 hours
                                                                • 9 BR
                                                                • 8 BA
                                                                • Sleeps 18
                                                                Villa #1934124
                                                                3
                                                                Viewed 64 times in the last 48 hours
                                                                  Very Good! 4/5
                                                                  (5 reviews)
                                                                  avg/night
                                                                  • 8 BR
                                                                  • 4 BA
                                                                  • Sleeps 16
                                                                  Villa #1934854
                                                                  5
                                                                  Viewed 31 times in the last 48 hours
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 3
                                                                    Multiple rentals Villa #6721451
                                                                      avg/night
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • Sleeps 4
                                                                      Multiple rentals Villa #6721451
                                                                      Viewed 18 times in the last 48 hours
                                                                        avg/night
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 3
                                                                        Multiple rentals Villa #6721451
                                                                        Viewed 8 times in the last 48 hours
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 2
                                                                          Multiple rentals Villa #6721451
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 2
                                                                            Multiple rentals Villa #6721451
                                                                              Wonderful! 4.9/5
                                                                              (9 reviews)
                                                                              avg/night
                                                                              • 4 BR
                                                                              • 4 BA
                                                                              • Separate Toilet
                                                                              • Sleeps 8
                                                                              Farmhouse #13754
                                                                              9
                                                                              Viewed 34 times in the last 48 hours
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                Multiple rentals Apartment #30993
                                                                                  • 5 BR
                                                                                  • 4 BA
                                                                                  • Sleeps 10
                                                                                  Villa #8155527
                                                                                  4
                                                                                    Exceptional! 5/5
                                                                                    (15 reviews)
                                                                                    avg/night
                                                                                    • 4 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 11
                                                                                    Villa #607748vb
                                                                                    15
                                                                                    Viewed 45 times in the last 48 hours
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 4
                                                                                      Apartment #6778439
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 6
                                                                                        Chateau / Country House #6738102
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 5
                                                                                          House #6799331
                                                                                            avg/night
                                                                                            • 5 BR
                                                                                            • 5 BA
                                                                                            • Sleeps 11
                                                                                            Villa #6556510
                                                                                            Viewed 5 times in the last 48 hours
                                                                                              Excellent! 4.7/5
                                                                                              (7 reviews)
                                                                                              avg/night
                                                                                              • 3 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 8
                                                                                              Villa #829953
                                                                                              7
                                                                                              Viewed 5 times in the last 48 hours
                                                                                                • 4 BR
                                                                                                • 4 BA
                                                                                                • Sleeps 8
                                                                                                Villa #1772008
                                                                                                  • 2 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 6
                                                                                                  Villa #1755396
                                                                                                  Viewed 29 times in the last 48 hours
                                                                                                    • 2 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 4
                                                                                                    Farmhouse #6734923
                                                                                                    • 1 - 50 of 300+
                                                                                                     

                                                                                                    Recent Reviews

                                                                                                    WE COULD NOT ASK FOR MORE

                                                                                                    5 of 5
                                                                                                    We read the reviews and thought this is for us! Two couples who enjoy spending their holidays together but also like to have their own privacy and space. This house was perfect! Well appointed, very elegantly furnished and with everything one might need for a cooking lesson. What fun we have had in learning how to make pasta. The owner Anna and her team gave us all the right tips to enjoy the house, the estate where it is located and the surrounding area. They were always there for us and they made our life so easy from our arrival until the end of our holiday (not to mention the welcome basket and drinks we found on arrival!). Our first time in Italy, we were a little daunted of not being able to find our way around in only one week. However everything went so smoothly and the hospitality offered was "luxurious" to say the least. Finally we must mention the fantastic place where the property is located, Arceno, unique in this part of the world and very exclusive. The villa is perfect for two couples but also for a family with two children. Thanks Anna for the fantastic experience. We are looking forward to another week of Tuscan "dolce vita".
                                                                                                    • Review Submitted: 17-Jan-2017
                                                                                                    • Date of Stay: Oct 2016

                                                                                                    Wonderful property, feel at home

                                                                                                    5 of 5
                                                                                                    We stayed at this wonderful property in September, four couples of friends from Philadelphia. The house is very comfortable, well looked after with lovely decor and many facilities. The garden is large with plenty of ornamental plants, and a beautiful view out front. We spent a lot of nice moments by the pool terrace, and the weather allowed us to enjoy swimming! The location of the property is excellent, in the countryside in a quiet area near Siena, reachable in 10 minutes. Florence, San Gimignano, Volterra, and other charming towns in the area are also quickly reachable, about half an hour! The owner was friendly and welcoming. She provided us with plentiful information on where to buy wine and oil, even organic. We visited the Enoteca Castellare in Chianti, where we had a great experience, tasting wine and Tuscan appetizers. We will recommend this property to our friends, and we hope to come back soon!
                                                                                                    • Review Submitted: 18-Dec-2016
                                                                                                    • Date of Stay: Sep 2016

                                                                                                    Wonderful villa in a beautiful setting

                                                                                                    4 of 5
                                                                                                    This is a beautiful villa, beautifully situated on a mountaintop with wonderful views of the Chianti region from every window of the villa. The villa works great for a multi-generational get-together, as it is divided into 3 separate apartments. The grounds of the villa are gorgeous and well-kept and the pool is well-maintained. A car is necessary for any outings, as the villa is quite remote and only accessed by dirt roads. There are no restaurants, shopping or other amenities within walking distance, so a vehicle is necessary to enjoy the wonderful Chianti area. We only have good things to say about the housekeeper/keyholder, who assisted us in many aspects. All in all the villa lived fully up to our expectations and more.
                                                                                                    • Review Submitted: 13-Oct-2016
                                                                                                    • Date of Stay: Sep 2016