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

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

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

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

Things to do in Chianti, Tuscany

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

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

Places to go on holiday in Chianti, Tuscany

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

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

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

Weather in Chianti, Tuscany

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

Travel to Chianti, Tuscany

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

  • Showing 1-50 of 300+
Additional service fee may apply.
  View Map Map
    Exceptional! 5/5
    (54 reviews)
    avg/night
    • 1 BR
    • 1 BA
    • Sleeps 4
    Multiple rentals Cottage #6049089
    54
    Viewed 89 times in the last 48 hours
      Exceptional! 5/5
      (12 reviews)
      avg/night
      • 4 BR
      • 4 BA
      • Sleeps 9
      Villa #602659vb
      12
      Viewed 59 times in the last 48 hours
        Excellent! 4.5/5
        (11 reviews)
        avg/night
        • 6 BR
        • 5 BA
        • Sleeps 12
        Villa #721562vb
        11
        Viewed 86 times in the last 48 hours
          Exceptional! 5/5
          (26 reviews)
          avg/night
          • 5 BR
          • 5 BA
          • Sleeps 10
          Villa #21478vb
          26
          Viewed 59 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 32 times in the last 48 hours
              Wonderful! 4.8/5
              (4 reviews)
              avg/night
              • 1 BR
              • 1 BA
              • Sleeps 3
              Multiple rentals Apartment #6622282
              4
              Viewed 10 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 14 times in the last 48 hours
                  Exceptional! 5/5
                  (37 reviews)
                  avg/night
                  • 3 BR
                  • 2 BA
                  • Sleeps 10
                  Villa #1137514
                  37
                  Viewed 54 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 38 times in the last 48 hours
                      Exceptional! 5/5
                      (43 reviews)
                      avg/night
                      • 2 BR
                      • 1 BA
                      • Sleeps 4
                      Multiple rentals Apartment #6055204
                      43
                      Viewed 24 times in the last 48 hours
                        Wonderful! 4.8/5
                        (27 reviews)
                        avg/night
                        • 2 BR
                        • 2 BA
                        • Sleeps 5
                        Apartment #6574247
                        27
                        Viewed 21 times in the last 48 hours
                          Exceptional! 5/5
                          (27 reviews)
                          avg/night
                          • 2 BR
                          • 1 BA
                          • Sleeps 5
                          Apartment #3880312
                          27
                          Viewed 19 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 48 times in the last 48 hours
                              Wonderful! 4.8/5
                              (18 reviews)
                              avg/night
                              • 3 BR
                              • 3 BA
                              • Sleeps 8
                              Villa #1729396
                              18
                              Viewed 30 times in the last 48 hours
                                Excellent! 4.5/5
                                (6 reviews)
                                avg/night
                                • 3 BR
                                • 2 BA
                                • Sleeps 9
                                Villa #1920987
                                6
                                Viewed 24 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 8 times in the last 48 hours
                                    Exceptional! 5/5
                                    (20 reviews)
                                    avg/night
                                    • 3 BR
                                    • 2 BA
                                    • Separate Toilet
                                    • Sleeps 7
                                    House #403492
                                    20
                                    Viewed 26 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 15 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 19 times in the last 48 hours
                                          Exceptional! 5/5
                                          (19 reviews)
                                          avg/night
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 8
                                          Villa #467172vb
                                          19
                                          Viewed 18 times in the last 48 hours
                                            Exceptional! 5/5
                                            (38 reviews)
                                            avg/night
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 4
                                            Multiple rentals Apartment #6055204
                                            38
                                            Viewed 22 times in the last 48 hours
                                              Exceptional! 5/5
                                              (12 reviews)
                                              avg/night
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 6
                                              Multiple rentals Chateau / Country House #6368329
                                              12
                                              Viewed 14 times in the last 48 hours
                                                Exceptional! 5/5
                                                (13 reviews)
                                                avg/night
                                                • 8 BR
                                                • 8 BA
                                                • Sleeps 16
                                                Villa #748934vb
                                                13
                                                Viewed 38 times in the last 48 hours
                                                  Exceptional! 5/5
                                                  (28 reviews)
                                                  avg/night
                                                  • 6 BR
                                                  • 5 BA
                                                  • Sleeps 11
                                                  Villa #999599
                                                  28
                                                  Viewed 45 times in the last 48 hours
                                                    Excellent! 4.7/5
                                                    (7 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 5
                                                    Barn #1697270
                                                    7
                                                    Viewed 49 times in the last 48 hours
                                                      Excellent! 4.7/5
                                                      (11 reviews)
                                                      View details for price
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 2
                                                      Multiple rentals Studio #632967a
                                                      11
                                                        Exceptional! 5/5
                                                        (46 reviews)
                                                        avg/night
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 5
                                                        Apartment #6196463
                                                        46
                                                        Viewed 20 times in the last 48 hours
                                                          • 4 BR
                                                          • 3 BA
                                                          • Sleeps 10
                                                          House #6042176
                                                          14
                                                          Viewed 29 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 25 times in the last 48 hours
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 2
                                                              Multiple rentals Apartment #1672740
                                                              2
                                                                Wonderful! 4.8/5
                                                                (20 reviews)
                                                                avg/night
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 2
                                                                Castle #825856
                                                                20
                                                                Viewed 33 times in the last 48 hours
                                                                  Excellent! 4.5/5
                                                                  (11 reviews)
                                                                  avg/night
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 4
                                                                  Apartment #70444
                                                                  11
                                                                  Viewed 19 times in the last 48 hours
                                                                    Wonderful! 4.9/5
                                                                    (8 reviews)
                                                                    avg/night
                                                                    • 4 BR
                                                                    • 2 BA
                                                                    • Sleeps 7
                                                                    Multiple rentals House #875022
                                                                    8
                                                                    Viewed 26 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (23 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 6
                                                                      House #1499766
                                                                      23
                                                                      Viewed 11 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 10 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (13 reviews)
                                                                          avg/night
                                                                          • 4 BR
                                                                          • 3 BA
                                                                          • Sleeps 8
                                                                          Chateau / Country House #1662564
                                                                          13
                                                                          Viewed 21 times in the last 48 hours
                                                                            Excellent! 4.6/5
                                                                            (9 reviews)
                                                                            avg/night
                                                                            • 5 BR
                                                                            • 4 BA
                                                                            • Sleeps 10
                                                                            Villa #663793vb
                                                                            9
                                                                            Viewed 16 times in the last 48 hours
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 8
                                                                              Farmhouse #3592356
                                                                                Exceptional! 5/5
                                                                                (5 reviews)
                                                                                avg/night
                                                                                • 8 BR
                                                                                • 8 BA
                                                                                • Separate Toilets
                                                                                • Sleeps 16
                                                                                Villa #804869vb
                                                                                5
                                                                                Viewed 24 times in the last 48 hours
                                                                                  Wonderful! 4.9/5
                                                                                  (29 reviews)
                                                                                  avg/night
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  Multiple rentals Farmhouse #450158
                                                                                  29
                                                                                  Viewed 9 times in the last 48 hours
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 8
                                                                                    Villa #1834327
                                                                                    22
                                                                                    Viewed 24 times in the last 48 hours
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Separate Toilet
                                                                                      • Sleeps 4
                                                                                      Cottage #1949277
                                                                                      1
                                                                                      Viewed 11 times in the last 48 hours
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 6
                                                                                        Multiple rentals Apartment #6622282
                                                                                        4
                                                                                        Viewed 5 times in the last 48 hours
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          Cottage #1949272
                                                                                          1
                                                                                          Viewed 30 times in the last 48 hours
                                                                                            Exceptional! 5/5
                                                                                            (22 reviews)
                                                                                            avg/night
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 4
                                                                                            Multiple rentals Chateau / Country House #6368329
                                                                                            22
                                                                                            Viewed 15 times in the last 48 hours
                                                                                              • 3 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 6
                                                                                              Villa #6790450
                                                                                              Viewed 13 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (32 reviews)
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 6
                                                                                                Cottage #602572a
                                                                                                32
                                                                                                Viewed 8 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 33 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (16 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 8
                                                                                                    Multiple rentals Chateau / Country House #6368329
                                                                                                    16
                                                                                                    Viewed 6 times in the last 48 hours
                                                                                                      Wonderful! 4.8/5
                                                                                                      (19 reviews)
                                                                                                      avg/night
                                                                                                      • 3 BR
                                                                                                      • 3 BA
                                                                                                      • Sleeps 6
                                                                                                      Apartment #6350241
                                                                                                      19
                                                                                                      Viewed 26 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      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

                                                                                                      Amazing host, amazing property

                                                                                                      5 of 5
                                                                                                      We stayed in cottage Murlo for 10 days, me my husband my mum and Auntie. From before we arrived Adela the lady who owns the property was absolutley amazing, from her directions to her property to telling us where the nearest supermarket was was just spot on. When we arrived we were greeted by Adela who showed us to our spotless accommodation which had everyting you would want. The pool was spotless and was cleaned every morning and most days we had the pool to oursevles which was great. During our stay we visited Florence, Siena, Pisa, & San Gimignano Adela told us the best places to park in each of these places which really helped alot. A Car is definitley needed if staying here but not too far to the local village to pick up your essentials or have morning coffee and a pastry which we did most mornings when not out sightseeing. Whilst you may find that owners staying onsite with you whilst on holiday a little off putting haveing Adela and her husband on site was great and really helped us thoroughly enjoy our stay. will definitley recommend staying here and will be returning at some point in the future. Thanks for a wonderful stay Adela.
                                                                                                      • Review Submitted: 25-Jul-2016
                                                                                                      • Date of Stay: Jul 2016

                                                                                                      Great country retreat

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