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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+
Additional service fee may apply.
    Exceptional! 5.0/5
    (54 reviews)
    avg/night
    • 1 BR
    • 1 BA
    • Sleeps 4
    Cottage #6049089
    54
    Viewed 61 times in the last 48 hours
      avg/night
      • 2 BR
      • 1 BA
      • Sleeps 6
      House #6565474
      4
      Viewed 89 times in the last 48 hours
        Exceptional! 5.0/5
        (19 reviews)
        avg/night
        • 3 BR
        • 2 BA
        • Sleeps 8
        Villa #467172vb
        19
        Viewed 30 times in the last 48 hours
          Exceptional! 5.0/5
          (13 reviews)
          avg/night
          • 4 BR
          • 2 BA
          • Sleeps 10
          Chateau / Country House #1939933
          13
          Viewed 28 times in the last 48 hours
            Excellent! 4.5/5
            (11 reviews)
            avg/night
            • 2 BR
            • 1 BA
            • Sleeps 4
            Apartment #70444
            11
            Viewed 14 times in the last 48 hours
              Excellent! 4.7/5
              (7 reviews)
              avg/night
              • 2 BR
              • 2 BA
              • Sleeps 5
              Barn #1697270
              7
              Viewed 21 times in the last 48 hours
                Exceptional! 5.0/5
                (5 reviews)
                avg/night
                • 4 BR
                • 2 BA
                • Separate Toilet
                • Sleeps 9
                House #6570358
                5
                Viewed 34 times in the last 48 hours
                  Wonderful! 4.9/5
                  (32 reviews)
                  avg/night
                  • 2 BR
                  • 1 BA
                  • Sleeps 6
                  Cottage #602572a
                  32
                  Viewed 28 times in the last 48 hours
                    Wonderful! 4.8/5
                    (14 reviews)
                    avg/night
                    • 4 BR
                    • 2 BA
                    • Sleeps 8
                    House #6041447
                    14
                    Viewed 14 times in the last 48 hours
                      Exceptional! 5.0/5
                      (5 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • Sleeps 7
                      Villa #1363507
                      5
                      Viewed 41 times in the last 48 hours
                        • 4 BR
                        • 4 BA
                        • Sleeps 8
                        Barn #866779
                        8
                          avg/night
                          • 3 BR
                          • 2 BA
                          • Sleeps 6
                          Apartment #1342045
                          2
                          Viewed 7 times in the last 48 hours
                            Excellent! 4.7/5
                            (10 reviews)
                            avg/night
                            • 4 BR
                            • 3 BA
                            • Sleeps 8
                            Castle #1618965
                            10
                            Viewed 33 times in the last 48 hours
                              avg/night
                              • 5 BR
                              • 2 BA
                              • Sleeps 6
                              House #399314vb
                              2
                              Viewed 9 times in the last 48 hours
                                Wonderful! 4.9/5
                                (19 reviews)
                                avg/night
                                • 10 BR
                                • 10 BA
                                • Sleeps 22
                                Villa #260642vb
                                19
                                Viewed 25 times in the last 48 hours
                                  Wonderful! 4.8/5
                                  (11 reviews)
                                  avg/night
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 6
                                  Apartment #6181119
                                  11
                                  Viewed 15 times in the last 48 hours
                                    • 2 BR
                                    • 2 BA
                                    • Sleeps 4
                                    Multiple rentals Apartment #750314
                                    2
                                    Viewed 14 times in the last 48 hours
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 4
                                      Multiple rentals Villa #750314
                                      1
                                      Viewed 29 times in the last 48 hours
                                        Excellent! 4.7/5
                                        (19 reviews)
                                        avg/night
                                        • 10 BR
                                        • 9 BA
                                        • Sleeps 21
                                        Villa #375042vb
                                        19
                                        Viewed 27 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (9 reviews)
                                          avg/night
                                          • 3 BR
                                          • 3 BA
                                          • Separate Toilet
                                          • Sleeps 8
                                          Apartment #1108069
                                          9
                                          Viewed 6 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (44 reviews)
                                            avg/night
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 6
                                            Farmhouse #6040012
                                            44
                                            Viewed 33 times in the last 48 hours
                                              • 2 BR
                                              • 1 BA
                                              • Sleeps 4
                                              Apartment #1645841
                                              3
                                                Wonderful! 4.8/5
                                                (8 reviews)
                                                avg/night
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 4
                                                Castle #1618971
                                                8
                                                Viewed 43 times in the last 48 hours
                                                  • 3 BR
                                                  • 3 BA
                                                  • Sleeps 7
                                                  Multiple rentals Apartment #750314
                                                  2
                                                  Viewed 14 times in the last 48 hours
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 2
                                                    Multiple rentals Apartment #750314
                                                    1
                                                      • 9 BR
                                                      • 10 BA
                                                      • Sleeps 18
                                                      Villa #1468820
                                                      Viewed 39 times in the last 48 hours
                                                        • 6 BR
                                                        • 5 BA
                                                        • Separate Toilet
                                                        • Sleeps 12
                                                        Villa #1150786
                                                          Exceptional! 5.0/5
                                                          (6 reviews)
                                                          avg/night
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 4
                                                          Multiple rentals Apartment #549490
                                                          6
                                                          Viewed 14 times in the last 48 hours
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 8
                                                            Multiple rentals Apartment #549490
                                                            1
                                                            Viewed 15 times in the last 48 hours
                                                              • 2 BR
                                                              • 1 BA
                                                              • Sleeps 5
                                                              Multiple rentals Apartment #549490
                                                              2
                                                              Viewed 26 times in the last 48 hours
                                                                avg/night
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 8
                                                                House #6254385
                                                                2
                                                                Viewed 8 times in the last 48 hours
                                                                  avg/night
                                                                  • 6 BR
                                                                  • 4 BA
                                                                  • Separate Toilet
                                                                  • Sleeps 12
                                                                  House #6046065
                                                                  2
                                                                  Viewed 9 times in the last 48 hours
                                                                    Wonderful! 4.8/5
                                                                    (14 reviews)
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 1 BA
                                                                    • Sleeps 6
                                                                    Farmhouse #6622709
                                                                    14
                                                                    Viewed 9 times in the last 48 hours
                                                                      Exceptional! 5.0/5
                                                                      (6 reviews)
                                                                      avg/night
                                                                      • 6 BR
                                                                      • 3 BA
                                                                      • Separate Toilet
                                                                      • Sleeps 12
                                                                      Villa #329513
                                                                      6
                                                                      Viewed 7 times in the last 48 hours
                                                                        avg/night
                                                                        • 5 BR
                                                                        • 3 BA
                                                                        • Sleeps 12
                                                                        House #6448731
                                                                        2
                                                                        Viewed 5 times in the last 48 hours
                                                                          Excellent! 4.7/5
                                                                          (15 reviews)
                                                                          avg/night
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 2
                                                                          Cottage #6621133
                                                                          15
                                                                          Viewed 5 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 23 times in the last 48 hours
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 4
                                                                              Castle #1618982
                                                                              2
                                                                              Viewed 5 times in the last 48 hours
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                Cottage #706749
                                                                                2
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  Castle #1619000
                                                                                  2
                                                                                    Excellent! 4.6/5
                                                                                    (5 reviews)
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 9
                                                                                    Apartment #1619059
                                                                                    5
                                                                                    Viewed 7 times in the last 48 hours
                                                                                      • 5 BR
                                                                                      • 4 BA
                                                                                      • Separate Toilet
                                                                                      • Sleeps 12
                                                                                      Villa #604226
                                                                                      3
                                                                                      Viewed 17 times in the last 48 hours
                                                                                        • 4 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 10
                                                                                        Cottage #6499636
                                                                                        2
                                                                                        Viewed 7 times in the last 48 hours
                                                                                          • 6 BR
                                                                                          • 5 BA
                                                                                          • Sleeps 12
                                                                                          Villa #1453677
                                                                                          Viewed 8 times in the last 48 hours
                                                                                            Excellent! 4.4/5
                                                                                            (18 reviews)
                                                                                            avg/night
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 8
                                                                                            House #6175336
                                                                                            18
                                                                                            Viewed 70 times in the last 48 hours
                                                                                              • 2 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 6
                                                                                              Multiple rentals Farmhouse #864013
                                                                                              3
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 4
                                                                                                Multiple rentals Farmhouse #864013
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 2
                                                                                                  Multiple rentals Farmhouse #864013
                                                                                                    • 2 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 4
                                                                                                    Multiple rentals Apartment #864013
                                                                                                    • 1 - 50 of 300+

                                                                                                    Montespertoli Holiday Apartments & Villas (300+)

                                                                                                     

                                                                                                    Recent Reviews

                                                                                                    Review for stay from 30 December 2016 to 02 January 2017

                                                                                                    4 of 5
                                                                                                    il nostro appartamento si trovava nella dependance del castello, posto meraviglioso. L'appartamento è composto da 3 camere matrimoniali di cui una con bagno in camera e le altre due con bagno esterno (tutti e tre ristrutturati recentemente e con doccia ). al piano sopra c'è un'altra stanza senza porta con due letti singoli. Il proprietario della villa non lo abbiamo mai visto, per fortuna il custode Rodrigo ha fatto il possibile per farci avere la legna ed accedere il camino. Quella casa era gelida pur avendo richiesto l'accensione dei termosifoni con anticipo ( considerando il fatto che il riscaldamento si paga a parte 25 € al giorno). Siamo riusciti a scaldarla quando ormai era il momento di andare via. Non c'è il forno ma solo il microonde, è presenta la lavastoviglie senza detersivo e sale. Il custode veramente disponibile in tutto. è stato comunque un bel soggiorno che ci ha permesso anche di visitare Firenze con soli 30 minuti di macchina.
                                                                                                    • Review Submitted: 09-Jan-2017
                                                                                                    • Date of Stay: Dec 2016

                                                                                                    Review for stay from 24 October 2016 to 29 October 2016

                                                                                                    5 of 5
                                                                                                    Sehr romantisch, nettes Personal traumhaft schön gelegen
                                                                                                    • Review Submitted: 23-Nov-2016
                                                                                                    • Date of Stay: Oct 2016

                                                                                                    Perfect family holiday rental

                                                                                                    5 of 5
                                                                                                    Very clean and tidy house. Extremely spacious with plenty of seats both inside and out. Grounds were well kept. Everything we needed to ensure our family holiday in Tuscany was relaxing and comfortable. Owner was very helpful and available for any queries. Highly recommended for its stunning position- easy access to Pisa , Florence , Siena , Lucca and only an hour from coast. A holiday we won't forget.
                                                                                                    • Review Submitted: 06-Nov-2016
                                                                                                    • Date of Stay: Oct 2016