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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.

    Wonderful! 4.9/5
    (57 reviews)
    avg/night
    • 1 BR
    • 1 BA
    • Sleeps 4
    Multiple rentals Cottage #6049089
    57
    Viewed 79 times in the last 48 hours
      Exceptional! 5/5
      (29 reviews)
      avg/night
      • 5 BR
      • 5 BA
      • Sleeps 10
      Villa #21478vb
      29
      Viewed 59 times in the last 48 hours
        Exceptional! 5/5
        (15 reviews)
        avg/night
        • 4 BR
        • 4 BA
        • Sleeps 9
        Villa #602659vb
        15
        Viewed 33 times in the last 48 hours
          Wonderful! 4.9/5
          (21 reviews)
          avg/night
          • 3 BR
          • 2 BA
          • Separate Toilet
          • Sleeps 7
          House #403492
          21
          Viewed 23 times in the last 48 hours
            Exceptional! 5/5
            (48 reviews)
            avg/night
            • 2 BR
            • 1 BA
            • Sleeps 4
            Multiple rentals Apartment #6055204
            48
            Viewed 55 times in the last 48 hours
              Excellent! 4.5/5
              (12 reviews)
              avg/night
              • 6 BR
              • 5 BA
              • Sleeps 12
              Villa #721562vb
              12
              Viewed 19 times in the last 48 hours
                Wonderful! 4.9/5
                (41 reviews)
                avg/night
                • 2 BR
                • 2 BA
                • Sleeps 6
                Multiple rentals Apartment #632967a
                41
                Viewed 13 times in the last 48 hours
                  Wonderful! 4.8/5
                  (11 reviews)
                  avg/night
                  • 5 BR
                  • 4 BA
                  • Separate Toilet
                  • Sleeps 9
                  Villa #761658vb
                  11
                  Viewed 22 times in the last 48 hours
                    Exceptional! 5/5
                    (40 reviews)
                    avg/night
                    • 2 BR
                    • 1 BA
                    • Sleeps 4
                    Multiple rentals Apartment #6055204
                    40
                    Viewed 14 times in the last 48 hours
                      Wonderful! 4.9/5
                      (32 reviews)
                      avg/night
                      • 2 BR
                      • 2 BA
                      • Sleeps 5
                      Multiple rentals Chateau / Country House #6153067
                      32
                      Viewed 12 times in the last 48 hours
                        Wonderful! 4.8/5
                        (29 reviews)
                        avg/night
                        • 2 BR
                        • 2 BA
                        • Sleeps 5
                        Apartment #6574247
                        29
                        Viewed 13 times in the last 48 hours
                          Exceptional! 5/5
                          (14 reviews)
                          avg/night
                          • 8 BR
                          • 8 BA
                          • Sleeps 16
                          Villa #748934vb
                          14
                          Viewed 25 times in the last 48 hours
                            Wonderful! 4.9/5
                            (23 reviews)
                            avg/night
                            • 3 BR
                            • 2 BA
                            • Sleeps 6
                            Multiple rentals Apartment #809657
                            23
                            Viewed 7 times in the last 48 hours
                              Exceptional! 5/5
                              (22 reviews)
                              avg/night
                              • 2 BR
                              • 1 BA
                              • Sleeps 3
                              Multiple rentals Chateau / Country House #27152
                              22
                              Viewed 35 times in the last 48 hours
                                Exceptional! 5/5
                                (39 reviews)
                                avg/night
                                • 2 BR
                                • 2 BA
                                • Sleeps 6
                                Multiple rentals Chateau / Country House #6153067
                                39
                                Viewed 5 times in the last 48 hours
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 3
                                  Multiple rentals Chateau / Country House #27152
                                  3
                                  Viewed 24 times in the last 48 hours
                                    Exceptional! 5/5
                                    (28 reviews)
                                    avg/night
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 5
                                    Apartment #3880312
                                    28
                                    Viewed 24 times in the last 48 hours
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 3
                                      Multiple rentals Apartment #6622282
                                      5
                                        Wonderful! 4.9/5
                                        (20 reviews)
                                        avg/night
                                        • 5 BR
                                        • 4 BA
                                        • Sleeps 12
                                        Villa #90810
                                        20
                                        Viewed 14 times in the last 48 hours
                                          Wonderful! 4.8/5
                                          (13 reviews)
                                          avg/night
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 2
                                          Multiple rentals Apartment #809657
                                          13
                                          Viewed 5 times in the last 48 hours
                                            Excellent! 4.7/5
                                            (15 reviews)
                                            avg/night
                                            • 4 BR
                                            • 2 BA
                                            • Sleeps 8
                                            House #6041447
                                            15
                                            Viewed 17 times in the last 48 hours
                                              • 2 BR
                                              • 1 BA
                                              • Sleeps 4
                                              Cottage #1949272
                                              3
                                              Viewed 11 times in the last 48 hours
                                                Exceptional! 5/5
                                                (38 reviews)
                                                avg/night
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 10
                                                Villa #1137514
                                                38
                                                Viewed 23 times in the last 48 hours
                                                  Excellent! 4.7/5
                                                  (7 reviews)
                                                  avg/night
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 5
                                                  Barn #1697270
                                                  7
                                                  Viewed 10 times in the last 48 hours
                                                    Wonderful! 4.9/5
                                                    (17 reviews)
                                                    avg/night
                                                    • 4 BR
                                                    • 3 BA
                                                    • Sleeps 8
                                                    Chateau / Country House #1662564
                                                    17
                                                    Viewed 12 times in the last 48 hours
                                                      Wonderful! 4.9/5
                                                      (14 reviews)
                                                      avg/night
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      Multiple rentals Chateau / Country House #6368329
                                                      14
                                                      Viewed 9 times in the last 48 hours
                                                        Exceptional! 5/5
                                                        (19 reviews)
                                                        avg/night
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 8
                                                        Villa #467172vb
                                                        19
                                                        Viewed 19 times in the last 48 hours
                                                          • 3 BR
                                                          • 2 BA
                                                          • Separate Toilet
                                                          • Sleeps 7
                                                          Villa #6288732
                                                          7
                                                            Exceptional! 5/5
                                                            (13 reviews)
                                                            avg/night
                                                            • 9 BR
                                                            • 7 BA
                                                            • Separate Toilet
                                                            • Sleeps 18
                                                            Villa #620449vb
                                                            13
                                                            Viewed 39 times in the last 48 hours
                                                              Wonderful! 4.9/5
                                                              (29 reviews)
                                                              avg/night
                                                              • 4 BR
                                                              • 4 BA
                                                              • Separate Toilet
                                                              • Sleeps 11
                                                              Chateau / Country House #1687872
                                                              29
                                                              Viewed 8 times in the last 48 hours
                                                                Wonderful! 4.8/5
                                                                (31 reviews)
                                                                avg/night
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                Multiple rentals Farmhouse #450158
                                                                31
                                                                Viewed 10 times in the last 48 hours
                                                                  Wonderful! 4.9/5
                                                                  (35 reviews)
                                                                  avg/night
                                                                  • 3 BR
                                                                  • 3 BA
                                                                  • Sleeps 9
                                                                  Multiple rentals House #420494
                                                                  35
                                                                  Viewed 6 times in the last 48 hours
                                                                    Wonderful! 4.9/5
                                                                    (17 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 3 BA
                                                                    • Sleeps 8
                                                                    Multiple rentals Chateau / Country House #6368329
                                                                    17
                                                                    Viewed 9 times in the last 48 hours
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 8
                                                                      Farmhouse #3592356
                                                                        Excellent! 4.6/5
                                                                        (9 reviews)
                                                                        avg/night
                                                                        • 5 BR
                                                                        • 4 BA
                                                                        • Sleeps 10
                                                                        Villa #663793vb
                                                                        9
                                                                        Viewed 7 times in the last 48 hours
                                                                          Exceptional! 5/5
                                                                          (5 reviews)
                                                                          avg/night
                                                                          • 8 BR
                                                                          • 8 BA
                                                                          • Separate Toilets
                                                                          • Sleeps 16
                                                                          Villa #804869vb
                                                                          5
                                                                          Viewed 42 times in the last 48 hours
                                                                            Wonderful! 4.8/5
                                                                            (57 reviews)
                                                                            avg/night
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 4
                                                                            Multiple rentals House #420494
                                                                            57
                                                                            Viewed 11 times in the last 48 hours
                                                                              Excellent! 4.6/5
                                                                              (7 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 4
                                                                              Apartment #1888191
                                                                              7
                                                                              Viewed 6 times in the last 48 hours
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 3
                                                                                Apartment #1358278
                                                                                1
                                                                                  avg/night
                                                                                  • 4 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 8
                                                                                  Villa #6993828
                                                                                  1
                                                                                  Viewed 54 times in the last 48 hours
                                                                                    Exceptional! 5/5
                                                                                    (4 reviews)
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Separate Toilet
                                                                                    • Sleeps 8
                                                                                    Farmhouse #1842956
                                                                                    4
                                                                                    Viewed 19 times in the last 48 hours
                                                                                      Exceptional! 5/5
                                                                                      (46 reviews)
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 5
                                                                                      Apartment #6196463
                                                                                      46
                                                                                      Viewed 6 times in the last 48 hours
                                                                                        Excellent! 4.5/5
                                                                                        (6 reviews)
                                                                                        avg/night
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 9
                                                                                        Villa #1920987
                                                                                        6
                                                                                        Viewed 14 times in the last 48 hours
                                                                                          Exceptional! 5/5
                                                                                          (6 reviews)
                                                                                          avg/night
                                                                                          • 4 BR
                                                                                          • 3 BA
                                                                                          • Separate Toilet
                                                                                          • Sleeps 10
                                                                                          Villa #6862086
                                                                                          6
                                                                                          Viewed 5 times in the last 48 hours
                                                                                            • 3 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 6
                                                                                            Villa #6790450
                                                                                            Viewed 18 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (22 reviews)
                                                                                              avg/night
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 2
                                                                                              Castle #825856
                                                                                              22
                                                                                              Viewed 26 times in the last 48 hours
                                                                                                • 3 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 8
                                                                                                Villa #1658572
                                                                                                10
                                                                                                  Exceptional! 5/5
                                                                                                  (4 reviews)
                                                                                                  avg/night
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  Apartment #1350992a
                                                                                                  4
                                                                                                  Viewed 13 times in the last 48 hours
                                                                                                    Excellent! 4.7/5
                                                                                                    (18 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 5
                                                                                                    Cottage #6163
                                                                                                    18
                                                                                                    Viewed 7 times in the last 48 hours
                                                                                                      Exceptional! 5/5
                                                                                                      (8 reviews)
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 5
                                                                                                      Chateau / Country House #864792
                                                                                                      8
                                                                                                      Viewed 9 times in the last 48 hours
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                                                                                                      Recent Reviews

                                                                                                      Beautiful setting with a small caveat

                                                                                                      4 of 5
                                                                                                      We loved the property and the setting and Elisabeth could not have been a more welcoming host. Casa Podere and it's grounds are beautiful and the views of the surrounding countryside are everything we hoped Tuscany would be. We really liked San Casciano which is a short walk away and provided for most of our needs. We rented the apartment closest to the main house and it was well equipped for lazy days in the garden and eating in. The only downside to our stay was that the other rental apartment in the annex was also occupied and the noise between the two became quite intrusive (+ we couldn't use the beautiful terrace!). I think we were unlucky in that the other guests seemed somewhat nocturnal (and noisy) but nonetheless it spoiled the feeling of being somewhere peaceful and relaxing. Coming from central London I didn't expect more noise at night in the Tuscan hills. A small blot on our stay but something of which to be aware.
                                                                                                      • Review Submitted: May 17, 2017
                                                                                                      • Date of Stay: May 2017

                                                                                                      Fantastic place, terrific hosts

                                                                                                      5 of 5
                                                                                                      We stayed in a 3-bedroom villa in Il Bacio from April 22nd to 28th 2017 and loved every minute of it. All accommodations were exactly as described - beautiful, clean and comfortable. The hospitality of Sonia and Franco exceeded all expectations. We were running very late and arrived after 10 PM. They waited for us and greeted us warmly and helped to get settled. We were after a long drive and did not have a supper, so they brought bread, cheese, salami and wine for us - all delicious. The place is conveniently located for travel to Florence, Sienna, Pisa and all places in between. Additionally, we are very grateful to our hosts for pointing us towards many small towns and medieval villages in the area that we had a great pleasure visiting. Irina Zeman and Co
                                                                                                      • Review Submitted: May 02, 2017
                                                                                                      • Date of Stay: Apr 2017