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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 99 times in the last 48 hours
      Exceptional! 5/5
      (29 reviews)
      avg/night
      • 5 BR
      • 5 BA
      • Sleeps 10
      Villa #21478vb
      29
      Viewed 58 times in the last 48 hours
        Exceptional! 5/5
        (15 reviews)
        avg/night
        • 4 BR
        • 4 BA
        • Sleeps 9
        Villa #602659vb
        15
        Viewed 25 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 14 times in the last 48 hours
            Excellent! 4.5/5
            (12 reviews)
            avg/night
            • 6 BR
            • 5 BA
            • Sleeps 12
            Villa #721562vb
            12
            Viewed 70 times in the last 48 hours
              Wonderful! 4.9/5
              (39 reviews)
              avg/night
              • 2 BR
              • 2 BA
              • Sleeps 6
              Multiple rentals Apartment #632967a
              39
              Viewed 24 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 45 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 34 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 27 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 19 times in the last 48 hours
                        Wonderful! 4.8/5
                        (29 reviews)
                        avg/night
                        • 2 BR
                        • 2 BA
                        • Sleeps 5
                        Apartment #6574247
                        29
                        Viewed 16 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 9 times in the last 48 hours
                            Excellent! 4.7/5
                            (10 reviews)
                            avg/night
                            • 5 BR
                            • 4 BA
                            • Separate Toilet
                            • Sleeps 10
                            Multiple rentals Chateau / Country House #6679140
                            10
                            Viewed 48 times in the last 48 hours
                              Exceptional! 5/5
                              (14 reviews)
                              avg/night
                              • 8 BR
                              • 8 BA
                              • Sleeps 16
                              Villa #748934vb
                              14
                              Viewed 48 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 27 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 6 times in the last 48 hours
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 3
                                    Multiple rentals Chateau / Country House #27152
                                    3
                                    Viewed 21 times in the last 48 hours
                                      Exceptional! 5/5
                                      (28 reviews)
                                      avg/night
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 5
                                      Apartment #3880312
                                      28
                                      Viewed 19 times in the last 48 hours
                                        Excellent! 4.6/5
                                        (5 reviews)
                                        avg/night
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 3
                                        Multiple rentals Apartment #6622282
                                        5
                                        Viewed 8 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (20 reviews)
                                          avg/night
                                          • 5 BR
                                          • 4 BA
                                          • Sleeps 12
                                          Villa #90810
                                          20
                                          Viewed 34 times in the last 48 hours
                                            Wonderful! 4.8/5
                                            (12 reviews)
                                            avg/night
                                            • 1 BR
                                            • 1 BA
                                            • Sleeps 2
                                            Multiple rentals Apartment #809657
                                            12
                                            Viewed 16 times in the last 48 hours
                                              Excellent! 4.7/5
                                              (15 reviews)
                                              avg/night
                                              • 4 BR
                                              • 2 BA
                                              • Sleeps 8
                                              House #6041447
                                              15
                                              Viewed 11 times in the last 48 hours
                                                • 2 BR
                                                • 1 BA
                                                • Sleeps 4
                                                Cottage #1949272
                                                3
                                                Viewed 15 times in the last 48 hours
                                                  Exceptional! 5/5
                                                  (38 reviews)
                                                  avg/night
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 10
                                                  Villa #1137514
                                                  38
                                                  Viewed 29 times in the last 48 hours
                                                    Excellent! 4.7/5
                                                    (7 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 5
                                                    Barn #1697270
                                                    7
                                                    Viewed 21 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 28 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 15 times in the last 48 hours
                                                          Exceptional! 5/5
                                                          (19 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 8
                                                          Villa #467172vb
                                                          19
                                                          Viewed 20 times in the last 48 hours
                                                            Excellent! 4.7/5
                                                            (7 reviews)
                                                            avg/night
                                                            • 3 BR
                                                            • 2 BA
                                                            • Separate Toilet
                                                            • Sleeps 7
                                                            Villa #6288732
                                                            7
                                                            Viewed 14 times in the last 48 hours
                                                              Exceptional! 5/5
                                                              (13 reviews)
                                                              avg/night
                                                              • 9 BR
                                                              • 7 BA
                                                              • Separate Toilet
                                                              • Sleeps 18
                                                              Villa #620449vb
                                                              13
                                                              Viewed 50 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 30 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 9 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
                                                                      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 25 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 10 times in the last 48 hours
                                                                              Excellent! 4.6/5
                                                                              (7 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 4
                                                                              Apartment #1888191
                                                                              7
                                                                                Exceptional! 5/5
                                                                                (1 reviews)
                                                                                avg/night
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 3
                                                                                Apartment #1358278
                                                                                1
                                                                                Viewed 6 times in the last 48 hours
                                                                                  avg/night
                                                                                  • 4 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 8
                                                                                  Villa #6993828
                                                                                  1
                                                                                  Viewed 61 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 24 times in the last 48 hours
                                                                                      Exceptional! 5/5
                                                                                      (46 reviews)
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 5
                                                                                      Apartment #6196463
                                                                                      46
                                                                                      Viewed 5 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 51 times in the last 48 hours
                                                                                          Excellent! 4.5/5
                                                                                          (6 reviews)
                                                                                          avg/night
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 9
                                                                                          Villa #1920987
                                                                                          6
                                                                                          Viewed 18 times in the last 48 hours
                                                                                            Exceptional! 5/5
                                                                                            (5 reviews)
                                                                                            avg/night
                                                                                            • 4 BR
                                                                                            • 3 BA
                                                                                            • Separate Toilet
                                                                                            • Sleeps 10
                                                                                            Villa #6862086
                                                                                            5
                                                                                            Viewed 13 times in the last 48 hours
                                                                                              • 3 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 6
                                                                                              Villa #6790450
                                                                                              Viewed 17 times in the last 48 hours
                                                                                                Wonderful! 4.8/5
                                                                                                (22 reviews)
                                                                                                avg/night
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 2
                                                                                                Castle #825856
                                                                                                22
                                                                                                Viewed 38 times in the last 48 hours
                                                                                                  Wonderful! 4.8/5
                                                                                                  (10 reviews)
                                                                                                  avg/night
                                                                                                  • 3 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 8
                                                                                                  Villa #1658572
                                                                                                  10
                                                                                                  Viewed 13 times in the last 48 hours
                                                                                                    Exceptional! 5/5
                                                                                                    (4 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 6
                                                                                                    Apartment #1350992a
                                                                                                    4
                                                                                                    Viewed 7 times in the last 48 hours
                                                                                                      Excellent! 4.7/5
                                                                                                      (18 reviews)
                                                                                                      avg/night
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 5
                                                                                                      Cottage #6163
                                                                                                      18
                                                                                                      Viewed 21 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