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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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    Wonderful! 4.9/5
    (21 reviews)
    avg/night
    • 3 BR
    • 3 BA
    • Sleeps 6
    Villa #421433
    21
    Viewed 51 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 20 times in the last 48 hours
        Wonderful! 4.9/5
        (30 reviews)
        avg/night
        • 3 BR
        • 3 BA
        • Separate Toilet
        • Sleeps 7
        Villa #709879vb
        30
        Viewed 46 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
            Wonderful! 4.9/5
            (30 reviews)
            avg/night
            • 5 BR
            • 5 BA
            • Sleeps 10
            Villa #275267
            30
            Viewed 62 times in the last 48 hours
              Excellent! 4.6/5
              (9 reviews)
              avg/night
              • 3 BR
              • 3 BA
              • Sleeps 6
              Farmhouse #8461
              9
              Viewed 24 times in the last 48 hours
                Exceptional! 5/5
                (44 reviews)
                avg/night
                • 2 BR
                • 2 BA
                • Sleeps 4
                Apartment #433025
                44
                Viewed 17 times in the last 48 hours
                  Wonderful! 4.8/5
                  (4 reviews)
                  avg/night
                  • 9 BR
                  • 8 BA
                  • Sleeps 18
                  Villa #1934124
                  4
                  Viewed 51 times in the last 48 hours
                    Exceptional! 5/5
                    (85 reviews)
                    avg/night
                    • 3 BR
                    • 3 BA
                    • Sleeps 6
                    Villa #95620
                    85
                    Viewed 22 times in the last 48 hours
                      Exceptional! 5/5
                      (50 reviews)
                      avg/night
                      • 3 BR
                      • 3 BA
                      • Sleeps 6
                      Multiple rentals Villa #64960
                      50
                      Viewed 43 times in the last 48 hours
                        Wonderful! 4.8/5
                        (25 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 7
                        Multiple rentals Villa #401530
                        25
                        Viewed 39 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 84 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 19 times in the last 48 hours
                              • 9 BR
                              • 5 BA
                              • Sleeps 18
                              Multiple rentals Villa #1140076
                              16
                              Viewed 11 times in the last 48 hours
                                • 1 BR
                                • 1 BA
                                • Sleeps 4
                                Multiple rentals Apartment #401530
                                8
                                Viewed 26 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 28 times in the last 48 hours
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 3
                                    Multiple rentals Apartment #401530
                                    15
                                      Exceptional! 5/5
                                      (12 reviews)
                                      avg/night
                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 8
                                      Multiple rentals Farmhouse #1140076
                                      12
                                      Viewed 13 times in the last 48 hours
                                        • 5 BR
                                        • 4 BA
                                        • Sleeps 14
                                        Multiple rentals Villa #401530
                                        6
                                        Viewed 26 times in the last 48 hours
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 3
                                          Multiple rentals Villa #6721451
                                            • 1 BR
                                            • 1 BA
                                            • Sleeps 4
                                            Multiple rentals Apartment #38930
                                            3
                                            Viewed 6 times in the last 48 hours
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 2
                                              Multiple rentals Apartment #1728813
                                              3
                                              Viewed 15 times in the last 48 hours
                                                • 2 BR
                                                • 1 BA
                                                • Separate Toilet
                                                • Sleeps 4
                                                Multiple rentals Apartment #1728813
                                                1
                                                Viewed 14 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 48 times in the last 48 hours
                                                    Exceptional! 5/5
                                                    (8 reviews)
                                                    avg/night
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    Multiple rentals Farmhouse #1140076
                                                    8
                                                    Viewed 16 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 8 times in the last 48 hours
                                                        • 8 BR
                                                        • 4 BA
                                                        • Separate Toilet
                                                        • Sleeps 15
                                                        Multiple rentals Chateau / Country House #1728813
                                                        1
                                                        Viewed 45 times in the last 48 hours
                                                          Exceptional! 5/5
                                                          (12 reviews)
                                                          avg/night
                                                          • 7 BR
                                                          • 4 BA
                                                          • Sleeps 14
                                                          Multiple rentals Farmhouse #1140076
                                                          12
                                                          Viewed 7 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 23 times in the last 48 hours
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 2
                                                              Multiple rentals Villa #6721451
                                                                avg/night
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 4
                                                                Multiple rentals Villa #6721451
                                                                Viewed 10 times in the last 48 hours
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 2
                                                                  Multiple rentals Villa #6721451
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 3
                                                                    Multiple rentals Villa #6721451
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 5
                                                                      Multiple rentals Farmhouse #1728813
                                                                      Viewed 21 times in the last 48 hours
                                                                        • 6 BR
                                                                        • 6 BA
                                                                        • Sleeps 12
                                                                        Villa #1228700
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                          Villa #1150760
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 4
                                                                            Multiple rentals Villa #79371
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 5
                                                                              Multiple rentals Villa #79371
                                                                              Viewed 7 times in the last 48 hours
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 3
                                                                                Multiple rentals Apartment #79371
                                                                                1
                                                                                  • 2 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  Multiple rentals Villa #79371
                                                                                  2
                                                                                  Viewed 14 times in the last 48 hours
                                                                                    • 1 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 3
                                                                                    Multiple rentals Villa #79371
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 6
                                                                                      Multiple rentals Farmhouse #6638853
                                                                                      Viewed 7 times in the last 48 hours
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 7
                                                                                        Multiple rentals Farmhouse #6638853
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 2 BA
                                                                                          • Separate Toilet
                                                                                          • Sleeps 6
                                                                                          Multiple rentals Farmhouse #6638853
                                                                                          Viewed 6 times in the last 48 hours
                                                                                            • 7 BR
                                                                                            • 6 BA
                                                                                            • Separate Toilet
                                                                                            • Sleeps 13
                                                                                            Villa #1150681
                                                                                              Wonderful! 4.9/5
                                                                                              (9 reviews)
                                                                                              avg/night
                                                                                              • 4 BR
                                                                                              • 4 BA
                                                                                              • Separate Toilet
                                                                                              • Sleeps 8
                                                                                              Farmhouse #13754
                                                                                              9
                                                                                              Viewed 28 times in the last 48 hours
                                                                                                Exceptional! 5/5
                                                                                                (13 reviews)
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 11
                                                                                                Villa #607748vb
                                                                                                13
                                                                                                Viewed 24 times in the last 48 hours
                                                                                                  • 6 BR
                                                                                                  • 5 BA
                                                                                                  • Sleeps 12
                                                                                                  Multiple rentals Villa #76109
                                                                                                  8
                                                                                                  Viewed 16 times in the last 48 hours
                                                                                                    Exceptional! 5/5
                                                                                                    (4 reviews)
                                                                                                    avg/night
                                                                                                    • 5 BR
                                                                                                    • 4 BA
                                                                                                    • Sleeps 10
                                                                                                    Villa #8155527
                                                                                                    4
                                                                                                    Viewed 7 times in the last 48 hours
                                                                                                      avg/night
                                                                                                      • 3 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 7
                                                                                                      Multiple rentals Farmhouse #1360933
                                                                                                      Viewed 9 times in the last 48 hours
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                                                                                                      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

                                                                                                      It's a beautiful property and does not disappoint.

                                                                                                      5 of 5
                                                                                                      We absolutely loved our stay at Club Monticello. We arrived late and had a nice welcome basket waiting on us with food and wine. The villa is very nice and fully equipped with anything you might need. The owners James and Penny were great and continued to spoil us with more wine and goodies. We used the concierge Rita and she helped set up the perfect tours, dinner reservations and cooking classes. The cooking class with Andrea was very fun for our entire family and the food was amazing. The location of the vineyard to Siena and Florence was great! We highly recommend and will definitely look to go visit again. You will not be disappointed.
                                                                                                      • Review Submitted: 04-Jan-2017
                                                                                                      • Date of Stay: Dec 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