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 Default Owner Icon heart-filled

Holidaymakers searching for holiday rentals in Montespertoli also enquired about villas in Cortona, apartments in Lucca and apartments in Florence Historic Centre

Make a holiday rental home or villa in Montespertoli, Florence, Italy your home away from home

Montespertoli is an old municipality of the world famous wine region of Chianti, which has been an important trading area since the Etruscan era, resulting in Montespertoli having a magnificent wine heritage and a countryside adorned with beautiful castles and chateaux of varying origins.

Things to do on holiday in Montespertoli, Italy

A tour of the Chianti countryside which surrounds any of the holiday accommodation in Montespertoli will take you to many strategic castle locations, including the beautiful castles of Botinaccio, Sonnino, Montefugoni, Lucardo and Poppiano. Throughout the region, walking holidays thrive, especially because of all the historical places of interest which adorn the landscape, meaning that there are plenty of places to pause and open your sandwiches, whilst taking in the views of the famous Tuscan countryside. Throughout the region visitors can find beautiful buildings, from chapels to fortifications, many of which contain beautiful artwork or important examples of sacred art.

Throughout the year, residents of Montespertoli villas and houses celebrate a range of festivals and carnivals, which are, without exception, colourful and joyful times to come and visit the town. The Chianti Festival in the first week of June, the ecological festival (Ecofesta) in October and the new wine festival (Festa del Vine Novello) and White Truffle Festival, both in November, fill the streets with stalls, exhibits and entertainment, and the abundance of local delicacies on offer mean that you will hardly need to cook from your self catering Montespertoli accommodation at all.

As you would expect from a region with such a long and respected tradition in wine, Montespertoli is a magnificent place in which to take a wine tasting holiday. The ‘roads of wine’ are ancient wine routes from Montespertoli to major settlements, which still provide the route for many walking and wine tasting holidays to this day.

Places to holiday in Montespertoli, Italy

When you take a Montespertoli apartment or villa, the town of Montaione will become familiar. It is a small but useful town, where you will find an array of fine shops, cheerful services and excellent little family owned restaurants, all surrounded by the beautiful grove covered countryside of Tuscany.

Weather in Montespertoli, Italy

Montespertoli is a wonderful holiday destination for those who enjoy the warmth but do not like it too hot. Average temperatures from late spring until early autumn remain around 22˚C, with daily peaks reaching around 30˚C, perfect for exploring the countryside or enjoying a glass of wine in a pavement café looking over the view.

Flights to Montespertoli, Italy

Montespertoli accommodation can be reached in under an hour from both Florence (FLR) and Pisa Airports (PSA), although Florence is slightly closer. Both airports receive direct flights from the UK throughout the year, with an increase in the number of scheduled flights throughout the peak months of July and August.

Showing 1-50 of 300+
  View Map Map
Additional service fee may apply.
    Wonderful! 4.9/5
    (60 reviews)
    avg/night
    • 1 BR
    • 1 BA
    • Sleeps 4
    Multiple rentals Cottage #6049089
    60
    Viewed 70 times in the last 48 hours
      Wonderful! 4.8/5
      (9 reviews)
      avg/night
      • 2 BR
      • 1 BA
      • Sleeps 6
      House #6565474
      9
      Viewed 22 times in the last 48 hours
        Exceptional! 5/5
        (7 reviews)
        avg/night
        • 4 BR
        • 2 BA
        • Separate Toilet
        • Sleeps 9
        House #6570358
        7
        Viewed 24 times in the last 48 hours
          Wonderful! 4.8/5
          (8 reviews)
          avg/night
          • 2 BR
          • 2 BA
          • Sleeps 5
          Barn #1697270
          8
          Viewed 10 times in the last 48 hours
            Excellent! 4.7/5
            (16 reviews)
            avg/night
            • 4 BR
            • 2 BA
            • Sleeps 8
            House #6041447
            16
            Viewed 13 times in the last 48 hours
              Exceptional! 5/5
              (22 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • Sleeps 8
              Villa #467172vb
              22
              Viewed 27 times in the last 48 hours
                • 2 BR
                • 1 BA
                • Sleeps 4
                Cottage #1949272
                4
                Viewed 8 times in the last 48 hours
                  • 3 BR
                  • 2 BA
                  • Sleeps 8
                  Farmhouse #3592356
                    Exceptional! 5/5
                    (14 reviews)
                    avg/night
                    • 4 BR
                    • 2 BA
                    • Sleeps 10
                    Chateau / Country House #1939933
                    14
                    Viewed 11 times in the last 48 hours
                      Good! 3.8/5
                      (9 reviews)
                      avg/night
                      • 2 BR
                      • 2 BA
                      • Sleeps 4
                      Castle #1618971
                      9
                      Viewed 33 times in the last 48 hours
                        Excellent! 4.7/5
                        (12 reviews)
                        avg/night
                        • 3 BR
                        • 3 BA
                        • Sleeps 8
                        Villa #1658572
                        12
                        Viewed 7 times in the last 48 hours
                          Wonderful! 4.8/5
                          (16 reviews)
                          avg/night
                          • 2 BR
                          • 1 BA
                          • Sleeps 6
                          Farmhouse #6622709
                          16
                          Viewed 16 times in the last 48 hours
                            • 2 BR
                            • 1 BA
                            • Separate Toilet
                            • Sleeps 4
                            Cottage #1949277
                            1
                              Excellent! 4.7/5
                              (12 reviews)
                              avg/night
                              • 4 BR
                              • 3 BA
                              • Sleeps 8
                              Castle #1618965
                              12
                              Viewed 28 times in the last 48 hours
                                Excellent! 4.5/5
                                (13 reviews)
                                avg/night
                                • 2 BR
                                • 1 BA
                                • Sleeps 4
                                Apartment #70444
                                13
                                Viewed 12 times in the last 48 hours
                                  Exceptional! 5/5
                                  (21 reviews)
                                  avg/night
                                  • 10 BR
                                  • 10 BA
                                  • Sleeps 22
                                  Villa #260642vb
                                  21
                                  Viewed 43 times in the last 48 hours
                                    Wonderful! 4.9/5
                                    (34 reviews)
                                    avg/night
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 6
                                    Cottage #602572a
                                    34
                                    Viewed 9 times in the last 48 hours
                                      Excellent! 4.6/5
                                      (8 reviews)
                                      avg/night
                                      • 6 BR
                                      • 4 BA
                                      • Sleeps 14
                                      House #1126435a
                                      8
                                      Viewed 27 times in the last 48 hours
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 6
                                        Multiple rentals Farmhouse #6040012
                                        44
                                        Viewed 7 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (9 reviews)
                                          avg/night
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 5
                                          House #212525vb
                                          9
                                            • 1 BR
                                            • 1 BA
                                            • Sleeps 2
                                            Multiple rentals Apartment #750314
                                            1
                                              • 3 BR
                                              • 3 BA
                                              • Sleeps 7
                                              Multiple rentals Apartment #750314
                                              2
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 4
                                                Multiple rentals Apartment #750314
                                                2
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 4
                                                  Multiple rentals Villa #750314
                                                  1
                                                  Viewed 6 times in the last 48 hours
                                                    • 6 BR
                                                    • 5 BA
                                                    • Separate Toilet
                                                    • Sleeps 12
                                                    Villa #1150786
                                                    Viewed 5 times in the last 48 hours
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 4
                                                      Multiple rentals Apartment #549490
                                                      6
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 5
                                                        Multiple rentals Apartment #549490
                                                        2
                                                        Viewed 7 times in the last 48 hours
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 8
                                                          Multiple rentals Apartment #549490
                                                          1
                                                          Viewed 7 times in the last 48 hours
                                                            • 5 BR
                                                            • 4 BA
                                                            • Sleeps 10
                                                            Villa #1078404
                                                            4
                                                              Exceptional! 5/5
                                                              (10 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 7
                                                              Villa #1363507
                                                              10
                                                              Viewed 8 times in the last 48 hours
                                                                Wonderful! 4.9/5
                                                                (14 reviews)
                                                                avg/night
                                                                • 8 BR
                                                                • 7 BA
                                                                • Separate Toilet
                                                                • Sleeps 15
                                                                Villa #6175567
                                                                14
                                                                  • 4 BR
                                                                  • 2 BA
                                                                  • Sleeps 10
                                                                  Villa #1092698
                                                                  4
                                                                  Viewed 5 times in the last 48 hours
                                                                    avg/night
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 4
                                                                    Multiple rentals Corporate Apartment #6049089
                                                                    Viewed 7 times in the last 48 hours
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • Sleeps 6
                                                                      Apartment #6181119
                                                                      13
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                        Chateau / Country House #860206
                                                                        8
                                                                          avg/night
                                                                          • 6 BR
                                                                          • 4 BA
                                                                          • Separate Toilet
                                                                          • Sleeps 12
                                                                          House #6046065
                                                                          2
                                                                          Viewed 9 times in the last 48 hours
                                                                            Excellent! 4.7/5
                                                                            (21 reviews)
                                                                            avg/night
                                                                            • 10 BR
                                                                            • 9 BA
                                                                            • Sleeps 21
                                                                            Villa #375042vb
                                                                            21
                                                                            Viewed 33 times in the last 48 hours
                                                                              Wonderful! 4.9/5
                                                                              (15 reviews)
                                                                              avg/night
                                                                              • 6 BR
                                                                              • 5 BA
                                                                              • Separate Toilet
                                                                              • Sleeps 12
                                                                              Villa #1192463
                                                                              15
                                                                              Viewed 30 times in the last 48 hours
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 2
                                                                                Castle #1618964
                                                                                2
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  Apartment #2152308
                                                                                  7
                                                                                    Wonderful! 4.9/5
                                                                                    (14 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 5
                                                                                    House #6446443
                                                                                    14
                                                                                    Viewed 7 times in the last 48 hours
                                                                                      Excellent! 4.5/5
                                                                                      (4 reviews)
                                                                                      avg/night
                                                                                      • 5 BR
                                                                                      • 4 BA
                                                                                      • Separate Toilet
                                                                                      • Sleeps 12
                                                                                      Villa #604226
                                                                                      4
                                                                                      Viewed 5 times in the last 48 hours
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        Apartment #6546441
                                                                                          • 2 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 5
                                                                                          Apartment #858065vb
                                                                                          1
                                                                                          Viewed 5 times in the last 48 hours
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 6
                                                                                            Villa #6850754
                                                                                            1
                                                                                              avg/night
                                                                                              • 4 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 9
                                                                                              Castle #1618997
                                                                                              4
                                                                                              Viewed 11 times in the last 48 hours
                                                                                                • 4 BR
                                                                                                • 4 BA
                                                                                                • Separate Toilet
                                                                                                • Sleeps 8
                                                                                                Barn #866779
                                                                                                10
                                                                                                  • 2 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 4
                                                                                                  Castle #1618982
                                                                                                  3
                                                                                                    Wonderful! 4.8/5
                                                                                                    (9 reviews)
                                                                                                    avg/night
                                                                                                    • 2 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 6
                                                                                                    Apartment #6679598
                                                                                                    9
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      Apartment #1342045
                                                                                                      2

                                                                                                      Montespertoli Holiday Apartments & Villas (300+)

                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      Fantastic place to relax

                                                                                                      5 of 5
                                                                                                      On many previous rentals we have been disappointed as the property did not live up to the details presented however this was not the case on this holiday, the property had everything we had hoped for and more. sometimes little things can make a difference and although they seem trivial can make a good holiday experience a great one. Angela and Stefania were friendly and helpful, and when we encountered a small issue it was resolved straightaway. The view from the balcony should be bottled and sold as it was a great way of spending an evening enjoying the sun set over the fields. I would highly recommend this property. Thank you Angela and Stefania
                                                                                                      • Review Submitted: Jul 17, 2017
                                                                                                      • Date of Stay: Jul 2017

                                                                                                      Review for stay from 26 June 2017 to 30 June 2017

                                                                                                      5 of 5
                                                                                                      Our apartment was wonderful and the castle beautiful! We loved our stay!
                                                                                                      • Review Submitted: Jul 07, 2017
                                                                                                      • Date of Stay: Jun 2017