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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.

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  • Showing 1-50 of 300+
Additional service fee may apply.
    Exceptional! 5.0/5
    (60 reviews)
    avg/night
    • 2 BR
    • 1 BA
    • Sleeps 4
    Multiple rentals Apartment #6029171
    60
    Viewed 43 times in the last 48 hours
      Exceptional! 5.0/5
      (72 reviews)
      avg/night
      • 2 BR
      • 3 BA
      • Separate Toilet
      • Sleeps 5
      Multiple rentals Cottage #6029171
      72
      Viewed 38 times in the last 48 hours
        • 2 BR
        • 2 BA
        • Sleeps 4
        Apartment #433025
        42
          • 3 BR
          • 3 BA
          • Sleeps 6
          Villa #95620
          84
            Wonderful! 4.9/5
            (30 reviews)
            avg/night
            • 3 BR
            • 3 BA
            • Separate Toilet
            • Sleeps 7
            Villa #709879vb
            30
            Viewed 13 times in the last 48 hours
              • 3 BR
              • 3 BA
              • Sleeps 6
              Villa #421433
              20
                Excellent! 4.6/5
                (9 reviews)
                avg/night
                • 3 BR
                • 3 BA
                • Sleeps 6
                Farmhouse #8461
                9
                Viewed 10 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 5 times in the last 48 hours
                    Wonderful! 4.9/5
                    (30 reviews)
                    avg/night
                    • 5 BR
                    • 5 BA
                    • Sleeps 10
                    Villa #275267
                    30
                    Viewed 13 times in the last 48 hours
                      • 9 BR
                      • 8 BA
                      • Sleeps 18
                      Villa #1934124
                      2
                      Viewed 25 times in the last 48 hours
                        Exceptional! 5.0/5
                        (48 reviews)
                        avg/night
                        • 3 BR
                        • 3 BA
                        • Sleeps 6
                        Multiple rentals Villa #64960
                        48
                        Viewed 13 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 5 times in the last 48 hours
                            Exceptional! 5.0/5
                            (12 reviews)
                            avg/night
                            • 7 BR
                            • 4 BA
                            • Sleeps 14
                            Multiple rentals Farmhouse #1140076
                            12
                            Viewed 5 times in the last 48 hours
                              Exceptional! 5.0/5
                              (8 reviews)
                              avg/night
                              • 3 BR
                              • 2 BA
                              • Sleeps 6
                              Multiple rentals Farmhouse #1140076
                              8
                              Viewed 11 times in the last 48 hours
                                • 9 BR
                                • 5 BA
                                • Sleeps 18
                                Multiple rentals Villa #1140076
                                16
                                Viewed 5 times in the last 48 hours
                                  • 4 BR
                                  • 2 BA
                                  • Sleeps 8
                                  Multiple rentals Farmhouse #1140076
                                  12
                                    Wonderful! 4.9/5
                                    (8 reviews)
                                    avg/night
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 5
                                    Multiple rentals Farmhouse #1140076
                                    8
                                    Viewed 7 times in the last 48 hours
                                      • 8 BR
                                      • 4 BA
                                      • Sleeps 16
                                      Villa #1934854
                                      5
                                        • 5 BR
                                        • 4 BA
                                        • Sleeps 14
                                        Multiple rentals Villa #401530
                                        5
                                        Viewed 19 times in the last 48 hours
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 4
                                          Multiple rentals Apartment #401530
                                          8
                                            Wonderful! 4.8/5
                                            (25 reviews)
                                            avg/night
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 7
                                            Multiple rentals Villa #401530
                                            25
                                            Viewed 15 times in the last 48 hours
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 3
                                              Multiple rentals Apartment #401530
                                              15
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 4
                                                Multiple rentals House #870971
                                                6
                                                  Wonderful! 4.9/5
                                                  (14 reviews)
                                                  avg/night
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 2
                                                  Multiple rentals Farmhouse #870971
                                                  14
                                                  Viewed 6 times in the last 48 hours
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    Multiple rentals House #870971
                                                    7
                                                      • 3 BR
                                                      • 3 BA
                                                      • Sleeps 6
                                                      Multiple rentals Castle #870971
                                                      6
                                                        avg/night
                                                        • 4 BR
                                                        • 4 BA
                                                        • Sleeps 8
                                                        Multiple rentals Farmhouse #870971
                                                        Viewed 6 times in the last 48 hours
                                                          • 7 BR
                                                          • 6 BA
                                                          • Sleeps 14
                                                          Villa #1004445
                                                          2
                                                            • 2 BR
                                                            • 1 BA
                                                            • Sleeps 6
                                                            Multiple rentals Farmhouse #6638853
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 7
                                                              Multiple rentals Farmhouse #6638853
                                                                • 2 BR
                                                                • 2 BA
                                                                • Separate Toilet
                                                                • Sleeps 6
                                                                Multiple rentals Farmhouse #6638853
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 2
                                                                  Multiple rentals Villa #6721451
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 2
                                                                    Multiple rentals Villa #6721451
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • Sleeps 4
                                                                      Multiple rentals Villa #6721451
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 3
                                                                        Multiple rentals Villa #6721451
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 3
                                                                          Multiple rentals Villa #6721451
                                                                            Excellent! 4.7/5
                                                                            (12 reviews)
                                                                            avg/night
                                                                            • 7 BR
                                                                            • 7 BA
                                                                            • Separate Toilets
                                                                            • Sleeps 15
                                                                            Farmhouse #443694vb
                                                                            12
                                                                            Viewed 10 times in the last 48 hours
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 5
                                                                              Multiple rentals Farmhouse #1728813
                                                                                • 8 BR
                                                                                • 4 BA
                                                                                • Separate Toilet
                                                                                • Sleeps 15
                                                                                Multiple rentals Chateau / Country House #1728813
                                                                                1
                                                                                Viewed 9 times in the last 48 hours
                                                                                  • 2 BR
                                                                                  • 1 BA
                                                                                  • Separate Toilet
                                                                                  • Sleeps 6
                                                                                  Multiple rentals House #38930
                                                                                  4
                                                                                    • 1 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    Multiple rentals Apartment #38930
                                                                                    3
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      Villa #1150760
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 5
                                                                                        Multiple rentals Villa #79371
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          Multiple rentals Villa #79371
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 3
                                                                                            Multiple rentals Apartment #79371
                                                                                            1
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              Multiple rentals Villa #79371
                                                                                              2
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 3
                                                                                                Multiple rentals Villa #79371
                                                                                                • 1 - 50 of 300+
                                                                                                 

                                                                                                Recent Reviews

                                                                                                Paradise in Tuscany!

                                                                                                5 of 5
                                                                                                We stayed at this stunning villa for 6 nights and were blown away. The pictures are nice but the villa itself has to be seen to be believed. We were 2 couples and we stayed in the 3 bedroom upstairs apartment and absolutely loved it. Less than a half hour from Sienna and about 1 hour from many popular destinations (San Gimignano, Montalcino, Montepulciano), we really had the time of our lives. We decided to take the italian cooking class with Enzo (the owner of the villa) and his 2 sons (Duccio and Max) and it was a night to remember. The sweetest people you can imagine and just mouth watering food and wine. They come to the villa, prepare their class, and then treat you to a 4 course meal of typical Tuscan cuisine. Definitely a highlight of our trip. Needless to say, we 100% recommend the villa. Romantic getaway, family vacation, travelling with friends, it's the perfect place to go. We were given a tour of the 2 bedroom apartment at the ground floor, equally stunning but we liked the fact that the upstairs had more than 1 bathroom. We left the villa with heavy hearts but I am certain that we will return one day. Can't wait!
                                                                                                • Review Submitted: 01-Dec-2016
                                                                                                • Date of Stay: Nov 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

                                                                                                Heavenly, beautiful, peacefull

                                                                                                5 of 5
                                                                                                The villa is more than I dreamed it would be. Comfortable, fully applianced kitchen, beautiful scenery and so close to Siena - 10 minutes Italian driver; 20 min. American driver! We were there for 3 Septembers - 2014/15/16 that's how much we liked it. the host family were exceptionally kind and generous. Anyone who spends time there will be the better for it. We loved every minute.
                                                                                                • Review Submitted: 10-Oct-2016
                                                                                                • Date of Stay: Sep 2016