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Holidaymakers searching for holiday rentals in Chianti also enquired about villas in Cortona, villas in Macerata and apartments in San Gimignano

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

An area of rolling hills and vineyard laden valleys, Chianti is a world famous section of the beautiful Province of Tuscany, Italy, famous for its wines. Situated between Florence and Siena, taking a Chianti villa rental not only puts you amongst the stunning rural scenery, surrounded by a selection of the best wines produced anywhere in the world, but also gives you access to some of the richest artistic heritage too. Self catering villas in Chianti, Tuscany, are a dream for wine connoisseurs everywhere.

Things to do in Chianti, Tuscany

The Tuscan countryside is ideal for exploration, by foot, on bicycle or, for those with a little less time or less energy, by car. Walking and cycling holidays using a Chianti rental villa are ideal, not only due to the idyllic setting and freedom provided, but also for the fact that there is very little that compares to the experience of sitting outside a self catering villa in Chianti, watching the sun set over the hills with a glass of local Chianti wine.

One of the nicest places to walk, relax and absorb the natural environment from a Chianti apartment rental or self catering villa is the Monte San Michele National Park, which lets you walk the hills to spectacular view points over hilltop towns and small vineyards bordered by woodland, well off the usual tourist trails.

Places to go on holiday in Chianti, Tuscany

Wine connoisseurs taking a villa in Chianti, Tuscany, will love Greve in September. Greve is the setting for the largest wine festival in Chianti, providing you the chance to sample, purchase and enjoy the huge variety of Chianti wines produced in the region.

San Casciano in the Val di Pesa is just 15km from Florence. San Casciano was a Roman outpost, and many of the old Roman villas, medieval fortresses and monasteries have now been turned into dramatic, luxury Chianti villas, overlooking the beautiful Val di Greve on one side and Val di Pesa to the other.

Impruneta is a rich, stately town bounded by the Florentine Hills and the rivers of both the Greve and Ema, with beautiful views and some magnificent restaurants and craft shops.

Weather in Chianti, Tuscany

Summers in Chianti are gloriously warm, with average daily temperatures from June until August of over 30°C, an average of 10°C higher than temperatures in the UK. Even during the winter, temperatures are over 10°C.

Travel to Chianti, Tuscany

Being ideally situated between Siena (SAY) and Florence (FLR) Airports, finding cheap flights to Chianti is easy, and reaching your self catering Chianti holiday villa is painless.

  • Showing 1-50 of 300+
Additional service fee may apply.
    Excellent! 4.5/5
    (8 reviews)
    avg/night
    • 6 BR
    • 5 BA
    • Sleeps 12
    Villa #721562vb
    8
    Viewed 68 times in the last 48 hours
      Exceptional! 5.0/5
      (54 reviews)
      avg/night
      • 1 BR
      • 1 BA
      • Sleeps 4
      Cottage #6049089
      54
      Viewed 104 times in the last 48 hours
        Exceptional! 5.0/5
        (12 reviews)
        avg/night
        • 4 BR
        • 4 BA
        • Sleeps 9
        Villa #602659vb
        12
        Viewed 128 times in the last 48 hours
          Wonderful! 4.9/5
          (38 reviews)
          avg/night
          • 2 BR
          • 2 BA
          • Sleeps 6
          Multiple rentals Apartment #632967a
          38
          Viewed 62 times in the last 48 hours
            Exceptional! 5.0/5
            (26 reviews)
            avg/night
            • 5 BR
            • 5 BA
            • Sleeps 10
            Villa #21478vb
            26
            Viewed 97 times in the last 48 hours
              Wonderful! 4.9/5
              (22 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • Sleeps 6
              Multiple rentals Apartment #809657
              22
              Viewed 23 times in the last 48 hours
                Wonderful! 4.8/5
                (9 reviews)
                avg/night
                • 5 BR
                • 4 BA
                • Separate Toilet
                • Sleeps 9
                Villa #761658vb
                9
                Viewed 48 times in the last 48 hours
                  Exceptional! 5.0/5
                  (37 reviews)
                  avg/night
                  • 3 BR
                  • 2 BA
                  • Sleeps 10
                  Villa #1137514
                  37
                  Viewed 86 times in the last 48 hours
                    • 1 BR
                    • 1 BA
                    • Sleeps 3
                    Multiple rentals Apartment #6622282
                    4
                    Viewed 29 times in the last 48 hours
                      Wonderful! 4.8/5
                      (18 reviews)
                      avg/night
                      • 3 BR
                      • 3 BA
                      • Sleeps 8
                      Villa #1729396
                      18
                      Viewed 68 times in the last 48 hours
                        Excellent! 4.5/5
                        (6 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 9
                        Villa #1920987
                        6
                        Viewed 46 times in the last 48 hours
                          Wonderful! 4.8/5
                          (11 reviews)
                          avg/night
                          • 1 BR
                          • 1 BA
                          • Sleeps 2
                          Multiple rentals Apartment #809657
                          11
                          Viewed 43 times in the last 48 hours
                            Wonderful! 4.9/5
                            (14 reviews)
                            avg/night
                            • 4 BR
                            • 3 BA
                            • Sleeps 10
                            House #6042176
                            14
                            Viewed 106 times in the last 48 hours
                              Exceptional! 5.0/5
                              (27 reviews)
                              avg/night
                              • 2 BR
                              • 1 BA
                              • Sleeps 5
                              Apartment #3880312
                              27
                              Viewed 16 times in the last 48 hours
                                Exceptional! 5.0/5
                                (12 reviews)
                                avg/night
                                • 2 BR
                                • 2 BA
                                • Sleeps 6
                                Multiple rentals Chateau / Country House #6368329
                                12
                                Viewed 22 times in the last 48 hours
                                  Exceptional! 5.0/5
                                  (28 reviews)
                                  avg/night
                                  • 5 BR
                                  • 4 BA
                                  • Sleeps 9
                                  Villa #999599
                                  28
                                  Viewed 45 times in the last 48 hours
                                    Exceptional! 5.0/5
                                    (39 reviews)
                                    avg/night
                                    • 2 BR
                                    • 2 BA
                                    • Sleeps 6
                                    Multiple rentals Chateau / Country House #6153067
                                    39
                                    Viewed 46 times in the last 48 hours
                                      Wonderful! 4.9/5
                                      (23 reviews)
                                      avg/night
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 6
                                      House #1499766
                                      23
                                      Viewed 22 times in the last 48 hours
                                        Exceptional! 5.0/5
                                        (13 reviews)
                                        avg/night
                                        • 8 BR
                                        • 8 BA
                                        • Sleeps 16
                                        Villa #748934vb
                                        13
                                        Viewed 113 times in the last 48 hours
                                          Exceptional! 5.0/5
                                          (19 reviews)
                                          avg/night
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 8
                                          Villa #467172vb
                                          19
                                          Viewed 74 times in the last 48 hours
                                            Excellent! 4.7/5
                                            (9 reviews)
                                            avg/night
                                            • 5 BR
                                            • 4 BA
                                            • Separate Toilet
                                            • Sleeps 10
                                            Multiple rentals Chateau / Country House #6679140
                                            9
                                            Viewed 181 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (30 reviews)
                                              avg/night
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 5
                                              Multiple rentals Chateau / Country House #6153067
                                              30
                                              Viewed 28 times in the last 48 hours
                                                Exceptional! 5.0/5
                                                (43 reviews)
                                                avg/night
                                                • 2 BR
                                                • 1 BA
                                                • Sleeps 4
                                                Multiple rentals Apartment #6055204
                                                43
                                                Viewed 65 times in the last 48 hours
                                                  Excellent! 4.7/5
                                                  (10 reviews)
                                                  avg/night
                                                  • 3 BR
                                                  • 3 BA
                                                  • Sleeps 8
                                                  Villa #342134vb
                                                  10
                                                  Viewed 39 times in the last 48 hours
                                                    Wonderful! 4.8/5
                                                    (20 reviews)
                                                    avg/night
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 2
                                                    Castle #825856
                                                    20
                                                    Viewed 46 times in the last 48 hours
                                                      Wonderful! 4.8/5
                                                      (27 reviews)
                                                      avg/night
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 5
                                                      Apartment #6574247
                                                      27
                                                      Viewed 22 times in the last 48 hours
                                                        Exceptional! 5.0/5
                                                        (46 reviews)
                                                        avg/night
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 5
                                                        Apartment #6196463
                                                        46
                                                        Viewed 15 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (16 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 3 BA
                                                          • Sleeps 8
                                                          Multiple rentals Chateau / Country House #6368329
                                                          16
                                                          Viewed 41 times in the last 48 hours
                                                            Excellent! 4.7/5
                                                            (9 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 5
                                                            Villa #1722262
                                                            9
                                                            Viewed 37 times in the last 48 hours
                                                              Exceptional! 5.0/5
                                                              (22 reviews)
                                                              avg/night
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 4
                                                              Multiple rentals Chateau / Country House #6368329
                                                              22
                                                              Viewed 41 times in the last 48 hours
                                                                Excellent! 4.6/5
                                                                (9 reviews)
                                                                avg/night
                                                                • 5 BR
                                                                • 4 BA
                                                                • Sleeps 10
                                                                Villa #663793vb
                                                                9
                                                                Viewed 31 times in the last 48 hours
                                                                  Wonderful! 4.9/5
                                                                  (13 reviews)
                                                                  avg/night
                                                                  • 4 BR
                                                                  • 3 BA
                                                                  • Sleeps 8
                                                                  Chateau / Country House #1662564
                                                                  13
                                                                  Viewed 35 times in the last 48 hours
                                                                    Excellent! 4.6/5
                                                                    (9 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 3 BA
                                                                    • Sleeps 6
                                                                    Villa #1725169
                                                                    9
                                                                    Viewed 41 times in the last 48 hours
                                                                      Exceptional! 5.0/5
                                                                      (20 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Separate Toilet
                                                                      • Sleeps 7
                                                                      House #403492
                                                                      20
                                                                      Viewed 32 times in the last 48 hours
                                                                        • 3 BR
                                                                        • 3 BA
                                                                        • Sleeps 6
                                                                        Villa #6790450
                                                                        Viewed 30 times in the last 48 hours
                                                                          Excellent! 4.7/5
                                                                          (7 reviews)
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 5
                                                                          Barn #1697270
                                                                          7
                                                                          Viewed 24 times in the last 48 hours
                                                                            Wonderful! 4.9/5
                                                                            (29 reviews)
                                                                            avg/night
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 4
                                                                            Multiple rentals Farmhouse #450158
                                                                            29
                                                                            Viewed 38 times in the last 48 hours
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Separate Toilet
                                                                              • Sleeps 4
                                                                              Cottage #1949277
                                                                              1
                                                                              Viewed 16 times in the last 48 hours
                                                                                Exceptional! 5.0/5
                                                                                (38 reviews)
                                                                                avg/night
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                Multiple rentals Apartment #6055204
                                                                                38
                                                                                Viewed 41 times in the last 48 hours
                                                                                  • 2 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 6
                                                                                  Multiple rentals Apartment #6622282
                                                                                  4
                                                                                  Viewed 101 times in the last 48 hours
                                                                                    Wonderful! 4.8/5
                                                                                    (19 reviews)
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 6
                                                                                    Apartment #6350241
                                                                                    19
                                                                                    Viewed 95 times in the last 48 hours
                                                                                      Exceptional! 5.0/5
                                                                                      (9 reviews)
                                                                                      avg/night
                                                                                      • 9 BR
                                                                                      • 7 BA
                                                                                      • Separate Toilet
                                                                                      • Sleeps 18
                                                                                      Villa #620449vb
                                                                                      9
                                                                                      Viewed 52 times in the last 48 hours
                                                                                        Good! 3.9/5
                                                                                        (8 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        Multiple rentals Apartment #809657
                                                                                        8
                                                                                        Viewed 30 times in the last 48 hours
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 8
                                                                                          Villa #1834327
                                                                                          22
                                                                                          Viewed 45 times in the last 48 hours
                                                                                            Wonderful! 4.9/5
                                                                                            (7 reviews)
                                                                                            avg/night
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 5
                                                                                            Farmhouse #6576351
                                                                                            7
                                                                                            Viewed 44 times in the last 48 hours
                                                                                              Wonderful! 4.9/5
                                                                                              (32 reviews)
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 6
                                                                                              Cottage #602572a
                                                                                              32
                                                                                              Viewed 30 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (28 reviews)
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 4 BA
                                                                                                • Separate Toilet
                                                                                                • Sleeps 11
                                                                                                Chateau / Country House #1687872
                                                                                                28
                                                                                                Viewed 17 times in the last 48 hours
                                                                                                  Wonderful! 4.8/5
                                                                                                  (14 reviews)
                                                                                                  avg/night
                                                                                                  • 4 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 8
                                                                                                  House #6041447
                                                                                                  14
                                                                                                  Viewed 15 times in the last 48 hours
                                                                                                    • Studio
                                                                                                    • 1 BA
                                                                                                    • Sleeps 5
                                                                                                    Apartment #1473794a
                                                                                                    1
                                                                                                    • 1 - 50 of 300+
                                                                                                     

                                                                                                    Recent Reviews

                                                                                                    Perfect! ❤️🇮🇪

                                                                                                    5 of 5
                                                                                                    Perfect place ❤️ amazing view and nice swimmingpool.
                                                                                                    • Review Submitted: 01-Oct-2016
                                                                                                    • Date of Stay: Sep 2016

                                                                                                    Perfect rural retreat

                                                                                                    5 of 5
                                                                                                    Our stay here couldn't have been better . If you want to get away from the husle and busle this is the place . Picturesque peaceful charming and the owners Adela and Mario were lovely hard working people . We wish them all the best for the future and the dogs Nelson and bounty very cheeky but well behaved . Regards David and Elaine
                                                                                                    • Review Submitted: 22-Sep-2016
                                                                                                    • Date of Stay: Sep 2016

                                                                                                    Great country retreat

                                                                                                    4 of 5
                                                                                                    We stayed here for seven weeks and enjoyed seeing the seasons change in Tuscany and the weather go from rain and more rain to lovely bright sunny days in the last couple of weeks. The house is part of an old mill and is very rustic - Watching the waterfall under the house during the flooding rains was very interesting. It's in a great position to drive around Tuscany and further afield if you have the time. A fifteen minute drive down to the station at Figline Valdarno allows you to catch the train into Florence (thirty minutes) or other destinations in Tuscany and throughout Italy. Ponte Agli Stolli is a friendly little village and we enjoyed meeting the locals and practising our Italian. A couple of things to be aware of if you're booking this property - the wifi connection is very poor and we found we needed to drive to Figline to use emails and Internet. Another shock was the cost of the gas when calculated at the end of our stay. This wouldn't be a problem in summer, but it's a significant expense in cold weather. Also, there is a small shop in the village for daily essentials at reasonable prices but at Figline there's an excellent supermarket. On Saturdays and Sundays there's a pizza restaurant in the village which is fun to go to. We enjoyed our seven weeks in Tuscany and Ponte agli Stolli was a good base for us
                                                                                                    • Review Submitted: 19-Mar-2016
                                                                                                    • Date of Stay: Jan 2016