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 76 times in the last 48 hours
      Wonderful! 4.8/5
      (9 reviews)
      avg/night
      • 2 BR
      • 1 BA
      • Sleeps 6
      House #6565474
      9
      Viewed 23 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 28 times in the last 48 hours
          Wonderful! 4.8/5
          (8 reviews)
          avg/night
          • 2 BR
          • 2 BA
          • Sleeps 5
          Barn #1697270
          8
          Viewed 7 times in the last 48 hours
            Excellent! 4.7/5
            (16 reviews)
            avg/night
            • 4 BR
            • 2 BA
            • Sleeps 8
            House #6041447
            16
            Viewed 19 times in the last 48 hours
              Exceptional! 5/5
              (22 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • Sleeps 8
              Villa #467172vb
              22
              Viewed 25 times in the last 48 hours
                Excellent! 4.6/5
                (5 reviews)
                avg/night
                • 2 BR
                • 1 BA
                • Sleeps 4
                Cottage #1949272
                5
                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 9 times in the last 48 hours
                      Good! 3.8/5
                      (9 reviews)
                      avg/night
                      • 2 BR
                      • 2 BA
                      • Sleeps 4
                      Castle #1618971
                      9
                      Viewed 11 times in the last 48 hours
                        • 3 BR
                        • 3 BA
                        • Sleeps 8
                        Villa #1658572
                        12
                          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
                            avg/night
                            • 2 BR
                            • 1 BA
                            • Separate Toilet
                            • Sleeps 4
                            Cottage #1949277
                            1
                            Viewed 5 times in the last 48 hours
                              Excellent! 4.7/5
                              (12 reviews)
                              avg/night
                              • 4 BR
                              • 3 BA
                              • Sleeps 8
                              Castle #1618965
                              12
                              Viewed 15 times in the last 48 hours
                                Excellent! 4.5/5
                                (13 reviews)
                                avg/night
                                • 2 BR
                                • 1 BA
                                • Sleeps 4
                                Apartment #70444
                                13
                                Viewed 5 times in the last 48 hours
                                  Exceptional! 5/5
                                  (21 reviews)
                                  avg/night
                                  • 10 BR
                                  • 10 BA
                                  • Sleeps 22
                                  Villa #260642vb
                                  21
                                  Viewed 24 times in the last 48 hours
                                    Wonderful! 4.9/5
                                    (34 reviews)
                                    avg/night
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 6
                                    Cottage #602572a
                                    34
                                    Viewed 15 times in the last 48 hours
                                      Excellent! 4.6/5
                                      (8 reviews)
                                      avg/night
                                      • 6 BR
                                      • 4 BA
                                      • Sleeps 14
                                      House #1126435a
                                      8
                                      Viewed 16 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
                                                  • 6 BR
                                                  • 5 BA
                                                  • Separate Toilet
                                                  • Sleeps 12
                                                  Villa #1150786
                                                    Exceptional! 5/5
                                                    (6 reviews)
                                                    avg/night
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    Multiple rentals Apartment #549490
                                                    6
                                                    Viewed 5 times in the last 48 hours
                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 5
                                                      Multiple rentals Apartment #549490
                                                      2
                                                      Viewed 6 times in the last 48 hours
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 8
                                                        Multiple rentals Apartment #549490
                                                        1
                                                        Viewed 6 times in the last 48 hours
                                                          • 5 BR
                                                          • 4 BA
                                                          • Sleeps 10
                                                          Villa #1078404
                                                          4
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 7
                                                            Villa #1363507
                                                            10
                                                              Wonderful! 4.9/5
                                                              (14 reviews)
                                                              avg/night
                                                              • 8 BR
                                                              • 7 BA
                                                              • Separate Toilet
                                                              • Sleeps 15
                                                              Villa #6175567
                                                              14
                                                              Viewed 9 times in the last 48 hours
                                                                • 4 BR
                                                                • 2 BA
                                                                • Sleeps 10
                                                                Villa #1092698
                                                                4
                                                                  avg/night
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 4
                                                                  Multiple rentals Corporate Apartment #6049089
                                                                  Viewed 6 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
                                                                      9
                                                                        avg/night
                                                                        • 6 BR
                                                                        • 4 BA
                                                                        • Separate Toilet
                                                                        • Sleeps 12
                                                                        House #6046065
                                                                        2
                                                                        Viewed 8 times in the last 48 hours
                                                                          Excellent! 4.7/5
                                                                          (21 reviews)
                                                                          avg/night
                                                                          • 10 BR
                                                                          • 9 BA
                                                                          • Sleeps 21
                                                                          Villa #375042vb
                                                                          21
                                                                          Viewed 20 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 19 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 9 times in the last 48 hours
                                                                                    • 5 BR
                                                                                    • 4 BA
                                                                                    • Separate Toilet
                                                                                    • Sleeps 12
                                                                                    Villa #604226
                                                                                    4
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 4
                                                                                      Apartment #6546441
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 5
                                                                                        Apartment #858065vb
                                                                                        1
                                                                                        Viewed 8 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 7 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
                                                                                                  Viewed 5 times in the last 48 hours
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 6
                                                                                                    Apartment #1342045
                                                                                                    2

                                                                                                    Montespertoli Holiday Apartments & Villas (300+)

                                                                                                     

                                                                                                    Recent Reviews

                                                                                                    Lovely off the beaten track romantic property

                                                                                                    5 of 5
                                                                                                    For those who want a romantic away from it all stay this property is superb. Beautifully restored by the owners with a lovely outdoor pool and only two other guest properties it really was perfect for us on our honeymoon. Within easy travelling of Florence, Siena a car is a must but in terms of relaxing this was perfect. The owners are very helpful and happy to recommend any visits, restaurants that you may require. All in all a stunning break and highly recommended.
                                                                                                    • Review Submitted: Jul 22, 2017
                                                                                                    • Date of Stay: Jul 2017

                                                                                                    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