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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.

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  • Showing 1-50 of 300+
Additional service fee may apply.
    Excellent! 4.4/5
    (7 reviews)
    avg/night
    • 6 BR
    • 5 BA
    • Sleeps 12
    Villa #721562vb
    7
    Viewed 36 times in the last 48 hours
      Exceptional! 5.0/5
      (36 reviews)
      avg/night
      • 3 BR
      • 2 BA
      • Sleeps 10
      Villa #1137514
      36
      Viewed 41 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 5 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 30 times in the last 48 hours
            Exceptional! 5.0/5
            (12 reviews)
            avg/night
            • 4 BR
            • 4 BA
            • Sleeps 9
            Villa #602659vb
            12
            Viewed 24 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 7 times in the last 48 hours
                Exceptional! 5.0/5
                (25 reviews)
                avg/night
                • 5 BR
                • 5 BA
                • Sleeps 10
                Villa #21478vb
                25
                Viewed 21 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 20 times in the last 48 hours
                    Exceptional! 5.0/5
                    (54 reviews)
                    avg/night
                    • 1 BR
                    • 1 BA
                    • Sleeps 4
                    Cottage #6049089
                    54
                    Viewed 27 times in the last 48 hours
                      • 2 BR
                      • 2 BA
                      • Sleeps 6
                      Multiple rentals Chateau / Country House #6368329
                      12
                        Wonderful! 4.8/5
                        (18 reviews)
                        avg/night
                        • 3 BR
                        • 3 BA
                        • Sleeps 8
                        Villa #1729396
                        18
                        Viewed 11 times in the last 48 hours
                          • 1 BR
                          • 1 BA
                          • Sleeps 2
                          Multiple rentals Studio #632967a
                          11
                            Excellent! 4.5/5
                            (11 reviews)
                            avg/night
                            • 2 BR
                            • 1 BA
                            • Sleeps 4
                            Apartment #70444
                            11
                            Viewed 17 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 23 times in the last 48 hours
                                Exceptional! 5.0/5
                                (28 reviews)
                                avg/night
                                • 5 BR
                                • 4 BA
                                • Sleeps 9
                                Villa #999599
                                28
                                Viewed 6 times in the last 48 hours
                                  Exceptional! 5.0/5
                                  (25 reviews)
                                  avg/night
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 5
                                  Apartment #3880312
                                  25
                                  Viewed 5 times in the last 48 hours
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 4
                                    Multiple rentals Farmhouse #450158
                                    29
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 9
                                      Villa #1920987
                                      6
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 3
                                        Multiple rentals Apartment #6622282
                                        4
                                          Exceptional! 5.0/5
                                          (13 reviews)
                                          avg/night
                                          • 8 BR
                                          • 8 BA
                                          • Sleeps 16
                                          Villa #748934vb
                                          13
                                          Viewed 41 times in the last 48 hours
                                            Exceptional! 5.0/5
                                            (46 reviews)
                                            avg/night
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 5
                                            Apartment #6196463
                                            46
                                            Viewed 6 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 16 times in the last 48 hours
                                                Exceptional! 5.0/5
                                                (15 reviews)
                                                avg/night
                                                • 3 BR
                                                • 3 BA
                                                • Sleeps 8
                                                Multiple rentals Chateau / Country House #6368329
                                                15
                                                Viewed 19 times in the last 48 hours
                                                  Excellent! 4.7/5
                                                  (10 reviews)
                                                  avg/night
                                                  • 3 BR
                                                  • 3 BA
                                                  • Sleeps 8
                                                  Villa #342134vb
                                                  10
                                                  Viewed 35 times in the last 48 hours
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    House #1499766
                                                    23
                                                      • 8 BR
                                                      • 8 BA
                                                      • Separate Toilets
                                                      • Sleeps 16
                                                      Villa #804869vb
                                                      4
                                                      Viewed 7 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 10 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 5 times in the last 48 hours
                                                            Wonderful! 4.8/5
                                                            (26 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 5
                                                            Apartment #6574247
                                                            26
                                                              Wonderful! 4.9/5
                                                              (31 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 1 BA
                                                              • Sleeps 6
                                                              Cottage #602572a
                                                              31
                                                              Viewed 17 times in the last 48 hours
                                                                Wonderful! 4.8/5
                                                                (19 reviews)
                                                                avg/night
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 2
                                                                Castle #825856
                                                                19
                                                                Viewed 10 times in the last 48 hours
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 6
                                                                  Multiple rentals Apartment #6622282
                                                                  4
                                                                    • 3 BR
                                                                    • 3 BA
                                                                    • Sleeps 6
                                                                    Villa #6790450
                                                                      Excellent! 4.7/5
                                                                      (11 reviews)
                                                                      avg/night
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      Apartment #1319726a
                                                                      11
                                                                        Exceptional! 5.0/5
                                                                        (8 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 3 BA
                                                                        • Sleeps 6
                                                                        Villa #1725169
                                                                        8
                                                                        Viewed 30 times in the last 48 hours
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 8
                                                                          Villa #467172vb
                                                                          19
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 11
                                                                            Multiple rentals Chateau / Country House #6255150
                                                                            30
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Separate Toilet
                                                                              • Sleeps 4
                                                                              Cottage #1949277
                                                                              1
                                                                                Wonderful! 4.9/5
                                                                                (7 reviews)
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 5
                                                                                Farmhouse #6576351
                                                                                7
                                                                                  Excellent! 4.7/5
                                                                                  (9 reviews)
                                                                                  avg/night
                                                                                  • 2 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 5
                                                                                  Villa #1722262
                                                                                  9
                                                                                  Viewed 7 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 25 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 9 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 15 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 15 times in the last 48 hours
                                                                                            • Studio
                                                                                            • 1 BA
                                                                                            • Sleeps 5
                                                                                            Apartment #1473794a
                                                                                            1
                                                                                              • 2 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 6
                                                                                              Apartment #6181119
                                                                                              10
                                                                                                avg/night
                                                                                                • 5 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                House #399314vb
                                                                                                2
                                                                                                Viewed 9 times in the last 48 hours
                                                                                                  Wonderful! 4.9/5
                                                                                                  (7 reviews)
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  Cottage #469652vb
                                                                                                  7
                                                                                                  Viewed 11 times in the last 48 hours
                                                                                                    Wonderful! 4.8/5
                                                                                                    (18 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 6
                                                                                                    Apartment #6350241
                                                                                                    18
                                                                                                    Viewed 6 times in the last 48 hours
                                                                                                      Excellent! 4.7/5
                                                                                                      (7 reviews)
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 5
                                                                                                      Barn #1697270
                                                                                                      7
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      Great location and even better view

                                                                                                      5 of 5
                                                                                                      How can you put into words our first holiday in Florence. The villa was simply incredible! The orthopaedic mattresses were simply exceptional it was like sleeping on a cloud. We loved barbecuing in the evenings while sipping a glas of chianti. Florence was only 20 minutes drive from the villa. The roads a really easy and not as difficult as in other parts of Tuscany. Even my wife that had only been driving for a few months had no issues driving. Will definitely go back!!!
                                                                                                      • Review Submitted: 18-Oct-2016
                                                                                                      • Date of Stay: Sep 2016

                                                                                                      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