HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar

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.

Cancel Clear Filters Apply Filters

Property Type

Popular Searches

Payment Options

Facilities

Managed By

Local Area

Property Details

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!
  • 1 - 50 of 764
Additional service fee may apply.
    • 3 BR
    • 2 BA
    • Sleeps 6
    33
      • 2 BR
      • 1 BA
      • Sleeps 4
      59
        • 2 BR
        • 3 BA
        • Separate Toilet
        • Sleeps 5
        71
          • 2 BR
          • 2 BA
          • Sleeps 4
          143
            • 3 BR
            • 3 BA
            • Sleeps 6
            64
              • 3 BR
              • 3 BA
              • Sleeps 6
              19
                • 2 BR
                • 2 BA
                • Sleeps 4
                39
                  • 3 BR
                  • 2 BA
                  • Separate Toilet
                  • Sleeps 6
                  8
                    • 3 BR
                    • 3 BA
                    • Sleeps 6
                    8
                      • 3 BR
                      • 3 BA
                      • Sleeps 10
                      29
                        • 4 BR
                        • 3 BA
                        • Separate Toilet
                        • Sleeps 6
                        9
                          • 3 BR
                          • 3 BA
                          • Separate Toilet
                          • Sleeps 7
                          26
                            • 9 BR
                            • 8 BA
                            • Sleeps 18
                            2 Reviews
                              • 3 BR
                              • 2 BA
                              • Sleeps 7
                              23
                                • 8 BR
                                • 4 BA
                                • Sleeps 16
                                3
                                  • 3 BR
                                  • 3 BA
                                  • Sleeps 6
                                  46
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 4
                                    18
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 4
                                      6
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 2
                                        14
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 6
                                          6
                                            • 3 BR
                                            • 3 BA
                                            • Sleeps 6
                                            6
                                              • 4 BR
                                              • 4 BA
                                              • Sleeps 8
                                                • 7 BR
                                                • 6 BA
                                                • Sleeps 14
                                                2 Reviews
                                                  • 2 BR
                                                  • 1 BA
                                                  • Sleeps 6
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 7
                                                      • 2 BR
                                                      • 2 BA
                                                      • Separate Toilet
                                                      • Sleeps 6
                                                        • 8 BR
                                                        • 4 BA
                                                        • Separate Toilet
                                                        • Sleeps 15
                                                        1 Review
                                                          • 2 BR
                                                          • 1 BA
                                                          • Separate Toilet
                                                          • Sleeps 6
                                                          4
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            3
                                                              • 7 BR
                                                              • 7 BA
                                                              • Separate Toilets
                                                              • Sleeps 15
                                                              11
                                                                • 7 BR
                                                                • 4 BA
                                                                • Sleeps 14
                                                                11
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 6
                                                                  7
                                                                    • 4 BR
                                                                    • 2 BA
                                                                    • Sleeps 8
                                                                    12
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 5
                                                                      8
                                                                        • 12 BR
                                                                        • 11 BA
                                                                        • Sleeps 24
                                                                        6
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 2
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 2
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 4
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 3
                                                                                  • 2 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 5
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 3
                                                                                      1 Review
                                                                                      • 1 - 50 of 764
                                                                                       

                                                                                      Recent Reviews

                                                                                      Luxurious Tuscan home

                                                                                      5 of 5
                                                                                      Another very relaxing stay in this wonderful Tuscan property. Everything you could need has been thought of and provided. One week was too short!
                                                                                      • Review Submitted: 15-Sep-2016
                                                                                      • Date of Stay: Aug 2016

                                                                                      We absolutely loved the villa -

                                                                                      5 of 5
                                                                                      The grounds were beautiful & the villa was clean & had all of your amenities needed - you had everything you wanted to cook a meal & enjoy the surroundings. The owners made recommendations for whatever you needed & we're all great. We will definitely go back again - maria
                                                                                      • Review Submitted: 08-Sep-2016
                                                                                      • Date of Stay: Aug 2016

                                                                                      absolutely beautiful venue - truly lovely landlord

                                                                                      5 of 5
                                                                                      The house is absolutely beautiful. The hosts are warm and welcoming. Perfect condition - high class. The view from the terrace is stunning, the atmosphere historical and very calm. The perfect place for people who love to enjoy a quality stay in tuscany. We will be back...!
                                                                                      • Review Submitted: 06-Sep-2016
                                                                                      • Date of Stay: Aug 2016