Holiday Rentals in Montegrossi - Holiday Lettings - Villas

Close

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

5,031 Holiday homes

Great rentals within 20 miles that match your search

Distance approx 12.97 miles from Montegrossi

(5) Excellent 

    48

    Holiday villa in Greve in Chianti

    Province of Florence / Greve in Chianti

    9 20 1 night min

    • 9 bedrooms
    • sleeps 20
    • 1 night min
    • Nearest beach 100 km
    • Swimming pool
    • Child friendly

    from £828 / night

    £8,921 - £12,400 / week

    Book View

    from £828 / night

    Distance approx 11.45 miles from Montegrossi

    (3) Excellent 

      24

      Holiday apartment with shared pool in Tavarnelle Val di Pesa

      Province of Florence / Tavarnelle Val di Pesa

      2 7 5 nights min

      • 2 bedrooms
      • sleeps 7
      • 5 nights min
      • Swimming pool
      • Child friendly
      • Air conditioning

      from £143 / night

      £971 / week

      Book View

      Responds fast!
      avg. 1 hour 45 minutes

      from £143 / night

      Distance approx 10.47 miles from Montegrossi

      (12) Excellent 

        47

        Holiday villa with swimming pool in Greve in Chianti

        Province of Florence / Greve in Chianti

        9 18 1 night min

        • 9 bedrooms
        • sleeps 18
        • 1 night min
        • Nearest beach 130 km
        • Swimming pool
        • Child friendly

        from £618 / night

        £4,667 - £10,578 / week

        Book View

        from £618 / night

        Distance approx 15.66 miles from Montegrossi

          17

          Holiday home rental

          Impruneta / Falciani

          4 11 5 nights min

          • 4 bedrooms
          • sleeps 11
          • 5 nights min
          • Swimming pool
          • Child friendly
          • Pet friendly

          from £184 / night

          £1,018 / week

          Book View

          from £184 / night

          Distance approx 16.54 miles from Montegrossi

          (5) Excellent 

            85

            Holiday apartment rental

            Province of Florence / Barberino Val d'Elsa

            3 5 4 nights min

            • 3 bedrooms
            • sleeps 5
            • 4 nights min
            • Nearest beach 100 km
            • Swimming pool
            • Child friendly

            from £82 / night

            £570 - £1,105 / week

            Book View

            from £82 / night

            Distance approx 18.73 miles from Montegrossi

            (5) Very Good 

              52

              Lucignano holiday home rental

              Province of Arezzo / Lucignano

              4 8 min stay varies

              • 4 bedrooms
              • sleeps 8
              • min stay varies
              • Nearest beach 70 km
              • Swimming pool
              • Child friendly

              from £179 / night

              £1,116 - £1,785 / week

              Book View

              from £179 / night

              Distance approx 17.41 miles from Montegrossi

              (5) Excellent 

                20

                Tavarnelle Val di Pesa holiday farmhouse rental

                Province of Florence / Tavarnelle Val di Pesa

                2 6 min stay varies

                • 2 bedrooms
                • sleeps 6
                • min stay varies
                • Swimming pool
                • Child friendly
                • Air conditioning

                from £87 / night

                £593 - £991 / week

                Book View

                from £87 / night

                Distance approx 5.96 miles from Montegrossi

                (11) Very Good 

                  47

                  Holiday farmhouse in Castelnuovo Berardenga

                  Province of Siena / Castelnuovo Berardenga

                  2 4 2 nights min

                  • 2 bedrooms
                  • sleeps 4
                  • 2 nights min
                  • Child friendly
                  • Ask about pets

                  from £91 / night

                  £634 / week

                  Book View

                  from £91 / night

                  Distance approx 11.01 miles from Montegrossi

                  (1) Very Good 

                    32

                    Farmhouse rental in Castelfranco di Sopra with shared pool

                    Castelfranco Piandisco / Castelfranco di Sopra

                    1 3 min stay varies

                    • 1 bedroom
                    • sleeps 3
                    • min stay varies
                    • Swimming pool
                    • Child friendly
                    • Pet friendly

                    from £97 / night

                    £429 - £868 / week

                    Book View

                    from £97 / night

                    Distance approx 14.54 miles from Montegrossi

                    (9) Excellent 

                      25

                      Farmhouse rental in Tavarnelle Val di Pesa with swimming pool

                      Province of Florence / Tavarnelle Val di Pesa

                      3 6 min stay varies

                      • 3 bedrooms
                      • sleeps 6
                      • min stay varies
                      • Nearest beach 90 km
                      • Swimming pool
                      • Child friendly

                      from £103 / night

                      £715 - £1,430 / week

                      Book View

                      Responds fast!
                      avg. 2 hours 3 minutes

                      from £103 / night

                      Distance approx 12.77 miles from Montegrossi

                      (18) Very Good 

                      Certificate of Excellence

                        18

                        Apartment rental in Siena

                        Province of Siena / Siena

                        1 4 min stay varies

                        • 1 bedroom
                        • sleeps 4
                        • min stay varies
                        • Nearest beach 105 km
                        • Swimming pool
                        • Car not necessary

                        Certificate of Excellence

                        from £102 / night

                        £1,144 / week

                        Book View

                        from £102 / night

                        Distance approx 17.19 miles from Montegrossi

                        (4) Excellent 

                          15

                          San Casciano in Val di Pesa holiday villa rental

                          Province of Florence / San Casciano in Val di Pesa

                          5 11 7 nights min

                          • 5 bedrooms
                          • sleeps 11
                          • 7 nights min
                          • Swimming pool
                          • Child friendly
                          • Private garden

                          from £584 / night

                          £4,086 / week

                          Book View

                          from £584 / night

                          Distance approx 17.42 miles from Montegrossi

                          (16) Excellent 

                          Certificate of Excellence

                            10

                            Holiday townhouse with swimming pool in Sovicille

                            Province of Siena / Sovicille

                            2 5 2 nights min

                            • 2 bedrooms
                            • sleeps 5
                            • 2 nights min
                            • Nearest beach 72 km
                            • Swimming pool
                            • Child friendly

                            Certificate of Excellence

                            from £113 / night

                            £786 / week

                            Book View

                            from £113 / night

                            Distance approx 14.16 miles from Montegrossi

                            (2) Excellent 

                              21

                              Apartment rental in Campoli in Chianti with shared pool

                              San Casciano in Val di Pesa / Campoli in Chianti

                              2 6 3 nights min

                              • 2 bedrooms
                              • sleeps 6
                              • 3 nights min
                              • Swimming pool
                              • Child friendly
                              • Air conditioning

                              from £128 / night

                              £766 / week

                              Book View

                              from £128 / night

                              Distance approx 14.53 miles from Montegrossi

                                29

                                Holiday apartment with shared pool in San Polo in Chianti

                                Greve in Chianti / San Polo in Chianti

                                4 10 min stay varies

                                • 4 bedrooms
                                • sleeps 10
                                • min stay varies
                                • Swimming pool
                                • Child friendly
                                • Pet friendly

                                from £184 / night

                                £869 - £1,788 / week

                                Book View

                                Responds fast!
                                avg. 3 hours 1 minutes

                                from £184 / night

                                Distance approx 18.15 miles from Montegrossi

                                  10

                                  Apartment rental in San Casciano in Val di Pesa

                                  Province of Florence / San Casciano in Val di Pesa

                                  1 5 1 night min

                                  • 1 bedroom
                                  • sleeps 5
                                  • 1 night min
                                  • Child friendly
                                  • Air conditioning

                                  from £173 / night

                                  £713 / week

                                  Book View

                                  from £173 / night

                                  Distance approx 10.77 miles from Montegrossi

                                  (3) Very Good 

                                    20

                                    Holiday farmhouse with swimming pool in Greve in Chianti

                                    Province of Florence / Greve in Chianti

                                    3 8 2 nights min

                                    • 3 bedrooms
                                    • sleeps 8
                                    • 2 nights min
                                    • Swimming pool
                                    • Child friendly
                                    • Pet friendly

                                    from £511 / night

                                    £3,065 / week

                                    Book View

                                    from £511 / night

                                    Distance approx 10.01 miles from Montegrossi

                                    (2) Very Good 

                                      30

                                      Holiday home with swimming pool in San Donato in Poggio

                                      Tavarnelle Val di Pesa / San Donato in Poggio

                                      3 6 min stay varies

                                      • 3 bedrooms
                                      • sleeps 6
                                      • min stay varies
                                      • Swimming pool
                                      • Child friendly
                                      • Pet friendly

                                      from £196 / night

                                      £1,271 - £1,671 / week

                                      Book View

                                      from £196 / night

                                      Distance approx 16.81 miles from Montegrossi

                                      (1) Excellent 

                                        15

                                        Holiday apartment with swimming pool in Monte San Savino

                                        Province of Arezzo / Monte San Savino

                                        3 7 1 night min

                                        • 3 bedrooms
                                        • sleeps 7
                                        • 1 night min
                                        • Swimming pool
                                        • Air conditioning
                                        • Private garden

                                        from £154 / night

                                        £1,072 / week

                                        Book View

                                        from £154 / night

                                        Distance approx 17.93 miles from Montegrossi

                                        (3) Excellent 

                                          20

                                          Antella holiday cottage rental

                                          Bagno a Ripoli / Antella

                                          3 4 5 nights min

                                          • 3 bedrooms
                                          • sleeps 4
                                          • 5 nights min
                                          • Nearest beach 121 km
                                          • Swimming pool
                                          • Child friendly

                                          from £116 / night

                                          £815 / week

                                          Book View

                                          from £116 / night

                                          Distance approx 14.27 miles from Montegrossi

                                            17

                                            Campoli in Chianti holiday apartment rental

                                            San Casciano in Val di Pesa / Campoli in Chianti

                                            1 3 3 nights min

                                            • 1 bedroom
                                            • sleeps 3
                                            • 3 nights min
                                            • Swimming pool
                                            • Child friendly
                                            • Air conditioning

                                            from £92 / night

                                            £511 / week

                                            Book View

                                            from £92 / night

                                            Distance approx 18.39 miles from Montegrossi

                                            (32) Excellent 

                                              34

                                              San Casciano in Val di Pesa holiday farmhouse rental

                                              Province of Florence / San Casciano in Val di Pesa

                                              2 5 min stay varies

                                              • 2 bedrooms
                                              • sleeps 5
                                              • min stay varies
                                              • Nearest beach 83 km
                                              • Suitable for children age 5+
                                              • Car not necessary

                                              from £84 / night

                                              £537 - £944 / week

                                              Book View

                                              Responds fast!
                                              avg. 44 minutes

                                              from £84 / night

                                              Distance approx 5.95 miles from Montegrossi

                                              (6) Excellent 

                                                16

                                                Holiday apartment in Radda in Chianti

                                                Province of Siena / Radda in Chianti

                                                1 3 4 nights min

                                                • 1 bedroom
                                                • sleeps 3
                                                • 4 nights min
                                                • Child friendly
                                                • Ask about pets

                                                from £58 / night

                                                £401 / week

                                                Book View

                                                from £58 / night

                                                Distance approx 13.86 miles from Montegrossi

                                                  35

                                                  Farmhouse accommodation in Barberino Val d'Elsa with shared pool

                                                  Province of Florence / Barberino Val d'Elsa

                                                  2 4 4 nights min

                                                  • 2 bedrooms
                                                  • sleeps 4
                                                  • 4 nights min
                                                  • Swimming pool
                                                  • Child friendly

                                                  from £193 / night

                                                  £1,352 / week

                                                  Book View

                                                  from £193 / night

                                                  Distance approx 10.99 miles from Montegrossi

                                                    34

                                                    Loro Ciuffenna holiday apartment rental

                                                    Province of Arezzo / Loro Ciuffenna

                                                    2 3 min stay varies

                                                    • 2 bedrooms
                                                    • sleeps 3
                                                    • min stay varies
                                                    • Nearest beach 150 km
                                                    • Swimming pool
                                                    • Child friendly

                                                    from £57 / night

                                                    £297 - £532 / week

                                                    Book View

                                                    from £57 / night

                                                    Distance approx 17.18 miles from Montegrossi

                                                      14

                                                      Holiday villa with swimming pool, golf nearby in Impruneta

                                                      Province of Florence / Impruneta

                                                      5 9 4 nights min

                                                      • 5 bedrooms
                                                      • sleeps 9
                                                      • 4 nights min
                                                      • Swimming pool
                                                      • Child friendly
                                                      • Private garden

                                                      from £205 / night

                                                      £1,430 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 2 hours 57 minutes

                                                      from £205 / night

                                                      Distance approx 18.23 miles from Montegrossi

                                                      (4) Excellent 

                                                        32

                                                        Holiday villa with swimming pool in Capolona

                                                        Arezzo / Capolona

                                                        3 9 7 nights min

                                                        • 3 bedrooms
                                                        • sleeps 9
                                                        • 7 nights min
                                                        • Swimming pool
                                                        • Child friendly
                                                        • Air conditioning

                                                        from £132 / night

                                                        £920 / week

                                                        Book View

                                                        from £132 / night

                                                        Distance approx 17.45 miles from Montegrossi

                                                        (1) Excellent 

                                                          20

                                                          Marcialla holiday apartment rental

                                                          Certaldo / Marcialla

                                                          2 5 2 nights min

                                                          • 2 bedrooms
                                                          • sleeps 5
                                                          • 2 nights min
                                                          • Swimming pool
                                                          • Child friendly
                                                          • Air conditioning

                                                          from £82 / night

                                                          £572 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 2 hours 5 minutes

                                                          from £82 / night

                                                          Distance approx 5.73 miles from Montegrossi

                                                            25

                                                            Mercatale Valdarno holiday farmhouse rental

                                                            Bucine / Mercatale Valdarno

                                                            7 14 min stay varies

                                                            • 7 bedrooms
                                                            • sleeps 14
                                                            • min stay varies
                                                            • Swimming pool
                                                            • Child friendly
                                                            • Pet friendly

                                                            from £286 / night

                                                            £1,757 - £3,432 / week

                                                            Book View

                                                            from £286 / night

                                                            Distance approx 18.67 miles from Montegrossi

                                                              20

                                                              Holiday villa rental

                                                              Sovicille / Torri

                                                              1 4 4 nights min

                                                              • 1 bedroom
                                                              • sleeps 4
                                                              • 4 nights min
                                                              • Child friendly
                                                              • Air conditioning
                                                              • Ask about pets

                                                              from £92 / night

                                                              £511 / week

                                                              Book View

                                                              from £92 / night

                                                              Distance approx 8.52 miles from Montegrossi

                                                              (2) Very Good 

                                                                35

                                                                Holiday home in Figline e Incisa Valdarno

                                                                Province of Florence / Figline e Incisa Valdarno

                                                                3 6 3 nights min

                                                                • 3 bedrooms
                                                                • sleeps 6
                                                                • 3 nights min
                                                                • Nearest beach 170 km
                                                                • Child friendly
                                                                • Air conditioning

                                                                from £103 / night

                                                                £644 / week

                                                                Book View

                                                                from £103 / night

                                                                Distance approx 3.95 miles from Montegrossi

                                                                (2) Excellent 

                                                                  18

                                                                  Apartment rental in Radda in Chianti with shared pool

                                                                  Province of Siena / Radda in Chianti

                                                                  1 4 1 night min

                                                                  • 1 bedroom
                                                                  • sleeps 4
                                                                  • 1 night min
                                                                  • Nearest beach 140 km
                                                                  • Swimming pool
                                                                  • Child friendly

                                                                  from £92 / night

                                                                  £644 / week

                                                                  Book View

                                                                  from £92 / night

                                                                  Distance approx 17.44 miles from Montegrossi

                                                                    16

                                                                    Holiday apartment with shared pool in Arezzo

                                                                    Province of Arezzo / Arezzo

                                                                    2 5 6 nights min

                                                                    • 2 bedrooms
                                                                    • sleeps 5
                                                                    • 6 nights min
                                                                    • Swimming pool
                                                                    • Child friendly
                                                                    • Pet friendly

                                                                    from £123 / night

                                                                    £858 / week

                                                                    Book View

                                                                    from £123 / night

                                                                    Distance approx 18.75 miles from Montegrossi

                                                                      6

                                                                      Castelluccio, Arezzo holiday villa rental

                                                                      Province of Arezzo / Castelluccio, Arezzo

                                                                      1 3 1 night min

                                                                      • 1 bedroom
                                                                      • sleeps 3
                                                                      • 1 night min
                                                                      • Swimming pool
                                                                      • Child friendly
                                                                      • Air conditioning

                                                                      from £103 / night

                                                                      £501 / week

                                                                      Book View

                                                                      from £103 / night

                                                                      Distance approx 10.11 miles from Montegrossi

                                                                      (2) Excellent 

                                                                        23

                                                                        Villa rental in Greve in Chianti with swimming pool

                                                                        Province of Florence / Greve in Chianti

                                                                        5 10 1 night min

                                                                        • 5 bedrooms
                                                                        • sleeps 10
                                                                        • 1 night min
                                                                        • Nearest beach 129 km
                                                                        • Swimming pool
                                                                        • Child friendly

                                                                        from £459 / night

                                                                        £3,210 - £4,684 / week

                                                                        Book View

                                                                        from £459 / night

                                                                        Distance approx 11.07 miles from Montegrossi

                                                                        (12) Excellent 

                                                                          31

                                                                          Holiday b&b in Pieve A Presciano

                                                                          Pergine Valdarno / Pieve A Presciano

                                                                          2 5 3 nights min

                                                                          • 2 bedrooms
                                                                          • sleeps 5
                                                                          • 3 nights min
                                                                          • Nearest beach 110 km
                                                                          • Child friendly
                                                                          • Pet friendly

                                                                          from £36 / night

                                                                          £256 - £542 / week

                                                                          Book View

                                                                          from £36 / night

                                                                          Distance approx 13.04 miles from Montegrossi

                                                                            41

                                                                            Holiday farmhouse with shared pool in San Giustino Valdarno

                                                                            Province of Arezzo / San Giustino Valdarno

                                                                            3 7 min stay varies

                                                                            • 3 bedrooms
                                                                            • sleeps 7
                                                                            • min stay varies
                                                                            • Nearest beach 110 km
                                                                            • Swimming pool
                                                                            • Child friendly

                                                                            from £148 / night

                                                                            £1,021 - £1,807 / week

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 2 hours 12 minutes

                                                                            from £148 / night

                                                                            Distance approx 18.06 miles from Montegrossi

                                                                              5

                                                                              San Rocco a Pilli holiday apartment rental

                                                                              Sovicille / San Rocco a Pilli

                                                                              1 2 1 night min

                                                                              • 1 bedroom
                                                                              • sleeps 2
                                                                              • 1 night min

                                                                              from £123 / night

                                                                              £818 / week

                                                                              Book View

                                                                              from £123 / night

                                                                              Distance approx 12.94 miles from Montegrossi

                                                                              (1) Excellent 

                                                                                42

                                                                                Barberino Val d'Elsa holiday villa rental

                                                                                Province of Florence / Barberino Val d'Elsa

                                                                                5 11 min stay varies

                                                                                • 5 bedrooms
                                                                                • sleeps 11
                                                                                • min stay varies
                                                                                • Nearest beach 90 km
                                                                                • Swimming pool
                                                                                • Child friendly

                                                                                from £675 / night

                                                                                £4,495 - £5,414 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 3 hours 3 minutes

                                                                                from £675 / night

                                                                                Distance approx 17.36 miles from Montegrossi

                                                                                (25) Excellent 

                                                                                  50

                                                                                  Holiday villa with swimming pool in Impruneta

                                                                                  Province of Florence / Impruneta

                                                                                  5 10 min stay varies

                                                                                  • 5 bedrooms
                                                                                  • sleeps 10
                                                                                  • min stay varies
                                                                                  • Nearest beach 100 km
                                                                                  • Swimming pool
                                                                                  • Child friendly

                                                                                  from £460 / night

                                                                                  £3,218 - £5,062 / week

                                                                                  Book View

                                                                                  Responds fast!
                                                                                  avg. 1 hour 52 minutes

                                                                                  from £460 / night

                                                                                  Also consider