Apartments in Castel San Gimignano and Villas – Holiday Lettings - Holiday Rentals Castel San Gimignano

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5,917 Holiday homes

(37) Excellent 

Certificate of Excellence

    32

    Castel San Gimignano holiday apartment rental

    San Gimignano / Castel San Gimignano

    2 6 min stay varies

    • 2 bedrooms
    • sleeps 6
    • min stay varies
    • Nearest beach 55 km
    • Swimming pool
    • Child friendly

    Certificate of Excellence

    from £100 / night

    £447 - £744 / week

    Book View

    Responds fast!
    avg. 2 hours 45 minutes

    from £100 / night

    (31) Excellent 

    Certificate of Excellence

      43

      Castel San Gimignano holiday apartment rental

      San Gimignano / Castel San Gimignano

      3 6 min stay varies

      • 3 bedrooms
      • sleeps 6
      • min stay varies
      • Nearest beach 55 km
      • Swimming pool
      • Child friendly

      Certificate of Excellence

      from £110 / night

      £447 - £744 / week

      Book View

      Responds fast!
      avg. 2 hours 45 minutes

      from £110 / night

        26

        Holiday apartment accommodation

        San Gimignano / Castel San Gimignano

        2 5 4 nights min

        • 2 bedrooms
        • sleeps 5
        • 4 nights min
        • Child friendly
        • Ask about pets

        from £70 / night

        £447 / week

        Book View

        from £70 / night

        (2) Excellent 

          80

          Farmhouse rental in Castel San Gimignano with shared pool, golf nearby

          San Gimignano / Castel San Gimignano

          3 7 min stay varies

          • 3 bedrooms
          • sleeps 7
          • min stay varies
          • Nearest beach 70 km
          • Swimming pool
          • Child friendly

          from £199 / night

          £1,290 - £2,282 / week

          Book View

          from £199 / night

          (14) Excellent 

          Certificate of Excellence

            14

            Castel San Gimignano holiday apartment rental

            San Gimignano / Castel San Gimignano

            3 5 min stay varies

            • 3 bedrooms
            • sleeps 5
            • min stay varies
            • Nearest beach 55 km
            • Child friendly
            • Ask about pets

            Certificate of Excellence

            from £100 / night

            £447 - £744 / week

            Book View

            Responds fast!
            avg. 2 hours 45 minutes

            from £100 / night

              19

              Holiday apartment with swimming pool, golf nearby in Castel San Gimignano

              San Gimignano / Castel San Gimignano

              10 22 min stay varies

              • 10 bedrooms
              • sleeps 22
              • min stay varies
              • Nearest beach 70 km
              • Swimming pool
              • Child friendly

              from £596 / night

              £4,117 - £7,390 / week

              Book View

              from £596 / night

              (1) Very Good 

                39

                Farmhouse rental in Castel San Gimignano with shared pool

                San Gimignano / Castel San Gimignano

                3 7 min stay varies

                • 3 bedrooms
                • sleeps 7
                • min stay varies
                • Nearest beach 70 km
                • Swimming pool
                • Child friendly

                from £179 / night

                £1,191 - £2,183 / week

                Book View

                from £179 / night

                (1) Very Good 

                  57

                  Farmhouse rental in Castel San Gimignano with shared pool, golf nearby

                  San Gimignano / Castel San Gimignano

                  3 7 min stay varies

                  • 3 bedrooms
                  • sleeps 7
                  • min stay varies
                  • Nearest beach 80 km
                  • Swimming pool
                  • Child friendly

                  from £199 / night

                  £1,488 - £2,183 / week

                  Book View

                  from £199 / night

                  (1)  

                    28

                    Holiday cottage in Castel San Gimignano

                    San Gimignano / Castel San Gimignano

                    1 3 min stay varies

                    • 1 bedroom
                    • sleeps 3
                    • min stay varies
                    • Nearest beach 90 km
                    • Swimming pool
                    • Child friendly

                    from £70 / night

                    £447 - £744 / week

                    Book View

                    from £70 / night

                    (1) Excellent 

                      22

                      Holiday apartment with shared pool in Castel San Gimignano

                      San Gimignano / Castel San Gimignano

                      2 5 min stay varies

                      • 2 bedrooms
                      • sleeps 5
                      • min stay varies
                      • Nearest beach 65 km
                      • Swimming pool
                      • Child friendly

                      from £90 / night

                      £531 - £945 / week

                      Book View

                      from £90 / night

                        29

                        Apartment rental in Castel San Gimignano with shared pool

                        San Gimignano / Castel San Gimignano

                        1 2 min stay varies

                        • 1 bedroom
                        • sleeps 2
                        • min stay varies
                        • Swimming pool
                        • Air conditioning

                        from £62 / night

                        £421 - £782 / week

                        Book View

                        from £62 / night

                          24

                          Holiday home in Castel San Gimignano

                          San Gimignano / Castel San Gimignano

                          3 8 min stay varies

                          • 3 bedrooms
                          • sleeps 8
                          • min stay varies
                          • Child friendly

                          from £123 / night

                          £724 - £1,868 / week

                          Book View

                          from £123 / night

                            20

                            Holiday home in Castel San Gimignano

                            San Gimignano / Castel San Gimignano

                            2 5 min stay varies

                            • 2 bedrooms
                            • sleeps 5
                            • min stay varies
                            • Child friendly

                            from £61 / night

                            £424 - £861 / week

                            Book View

                            from £61 / night

                              35

                              Castel San Gimignano holiday apartment rental

                              San Gimignano / Castel San Gimignano

                              3 6 min stay varies

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

                              from £99 / night

                              £678 - £1,774 / week

                              Book View

                              from £99 / night

                                43

                                Apartment rental in Castel San Gimignano with shared pool

                                San Gimignano / Castel San Gimignano

                                1 3 7 nights min

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

                                from £73 / night

                                £505 - £1,191 / week

                                Book View

                                Responds fast!
                                avg. 2 hours 29 minutes

                                from £73 / night

                                  29

                                  Apartment rental in Castel San Gimignano with shared pool

                                  San Gimignano / Castel San Gimignano

                                  1 2 min stay varies

                                  • 1 bedroom
                                  • sleeps 2
                                  • min stay varies
                                  • Swimming pool
                                  • Air conditioning

                                  from £70 / night

                                  £478 - £889 / week

                                  Book View

                                  from £70 / night

                                    30

                                    Castel San Gimignano holiday apartment rental

                                    San Gimignano / Castel San Gimignano

                                    1 2 min stay varies

                                    • 1 bedroom
                                    • sleeps 2
                                    • min stay varies
                                    • Swimming pool
                                    • Child friendly
                                    • Air conditioning

                                    from £49 / night

                                    £337 - £884 / week

                                    Book View

                                    from £49 / night

                                      29

                                      Castel San Gimignano holiday apartment rental

                                      San Gimignano / Castel San Gimignano

                                      1 2 min stay varies

                                      • 1 bedroom
                                      • sleeps 2
                                      • min stay varies
                                      • Swimming pool
                                      • Child friendly
                                      • Air conditioning

                                      from £49 / night

                                      £337 - £884 / week

                                      Book View

                                      from £49 / night

                                        20

                                        Holiday apartment rental

                                        San Gimignano / Castel San Gimignano

                                        2 5 7 nights min

                                        • 2 bedrooms
                                        • sleeps 5
                                        • 7 nights min
                                        • Swimming pool
                                        • Child friendly
                                        • Ask about pets

                                        from £87 / night

                                        £605 - £1,142 / week

                                        Book View

                                        Responds fast!
                                        avg. 2 hours 21 minutes

                                        from £87 / night

                                          24

                                          Holiday villa with swimming pool in Castel San Gimignano

                                          San Gimignano / Castel San Gimignano

                                          3 8 7 nights min

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

                                          from £154 / night

                                          £1,072 - £1,643 / week

                                          Book View

                                          Responds fast!
                                          avg. 2 hours 29 minutes

                                          from £154 / night

                                            32

                                            Castel San Gimignano holiday apartment rental

                                            San Gimignano / Castel San Gimignano

                                            1 2 min stay varies

                                            • 1 bedroom
                                            • sleeps 2
                                            • min stay varies
                                            • Swimming pool
                                            • Child friendly
                                            • Air conditioning

                                            from £49 / night

                                            £337 - £884 / week

                                            Book View

                                            from £49 / night

                                              33

                                              Castel San Gimignano holiday apartment rental

                                              San Gimignano / Castel San Gimignano

                                              2 4 min stay varies

                                              • 2 bedrooms
                                              • sleeps 4
                                              • min stay varies
                                              • Swimming pool
                                              • Child friendly
                                              • Air conditioning

                                              from £59 / night

                                              £405 - £1,091 / week

                                              Book View

                                              from £59 / night

                                                29

                                                Holiday apartment with shared pool in Castel San Gimignano

                                                San Gimignano / Castel San Gimignano

                                                2 5 min stay varies

                                                • 2 bedrooms
                                                • sleeps 5
                                                • min stay varies
                                                • Swimming pool
                                                • Child friendly
                                                • Pet friendly

                                                from £58 / night

                                                £406 - £1,065 / week

                                                Book View

                                                from £58 / night

                                                  31

                                                  Castel San Gimignano holiday apartment rental

                                                  San Gimignano / Castel San Gimignano

                                                  1 2 min stay varies

                                                  • 1 bedroom
                                                  • sleeps 2
                                                  • min stay varies
                                                  • Swimming pool
                                                  • Child friendly
                                                  • Air conditioning

                                                  from £49 / night

                                                  £337 - £884 / week

                                                  Book View

                                                  from £49 / night

                                                    28

                                                    Apartment rental in Castel San Gimignano with shared pool

                                                    San Gimignano / Castel San Gimignano

                                                    1 2 min stay varies

                                                    • 1 bedroom
                                                    • sleeps 2
                                                    • min stay varies
                                                    • Swimming pool
                                                    • Air conditioning

                                                    from £62 / night

                                                    £421 - £782 / week

                                                    Book View

                                                    from £62 / night

                                                      34

                                                      Castel San Gimignano holiday apartment rental

                                                      San Gimignano / Castel San Gimignano

                                                      3 6 min stay varies

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

                                                      from £109 / night

                                                      £747 - £1,913 / week

                                                      Book View

                                                      from £109 / night

                                                        31

                                                        Castel San Gimignano holiday apartment rental

                                                        San Gimignano / Castel San Gimignano

                                                        2 4 min stay varies

                                                        • 2 bedrooms
                                                        • sleeps 4
                                                        • min stay varies
                                                        • Swimming pool
                                                        • Child friendly
                                                        • Air conditioning

                                                        from £59 / night

                                                        £405 - £1,090 / week

                                                        Book View

                                                        from £59 / night

                                                          28

                                                          Apartment rental in Castel San Gimignano with shared pool

                                                          San Gimignano / Castel San Gimignano

                                                          1 2 min stay varies

                                                          • 1 bedroom
                                                          • sleeps 2
                                                          • min stay varies
                                                          • Swimming pool
                                                          • Air conditioning

                                                          from £70 / night

                                                          £478 - £889 / week

                                                          Book View

                                                          from £70 / night

                                                            30

                                                            Castel San Gimignano holiday apartment rental

                                                            San Gimignano / Castel San Gimignano

                                                            1 2 min stay varies

                                                            • 1 bedroom
                                                            • sleeps 2
                                                            • min stay varies
                                                            • Swimming pool
                                                            • Child friendly
                                                            • Air conditioning

                                                            from £49 / night

                                                            £337 - £884 / week

                                                            Book View

                                                            from £49 / night

                                                              43

                                                              Holiday apartment with shared pool in Castel San Gimignano

                                                              San Gimignano / Castel San Gimignano

                                                              1 3 min stay varies

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

                                                              from £47 / night

                                                              £326 - £905 / week

                                                              Book View

                                                              Responds fast!
                                                              avg. 2 hours 3 minutes

                                                              from £47 / night

                                                                28

                                                                Castel San Gimignano holiday apartment rental

                                                                San Gimignano / Castel San Gimignano

                                                                1 2 min stay varies

                                                                • 1 bedroom
                                                                • sleeps 2
                                                                • min stay varies
                                                                • Swimming pool
                                                                • Air conditioning

                                                                from £62 / night

                                                                £421 - £782 / week

                                                                Book View

                                                                from £62 / night

                                                                  20

                                                                  Castel San Gimignano holiday apartment rental

                                                                  San Gimignano / Castel San Gimignano

                                                                  2 5 7 nights min

                                                                  • 2 bedrooms
                                                                  • sleeps 5
                                                                  • 7 nights min
                                                                  • Swimming pool
                                                                  • Child friendly
                                                                  • Ask about pets

                                                                  from £93 / night

                                                                  £650 - £1,239 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 2 hours 29 minutes

                                                                  from £93 / night

                                                                    29

                                                                    Castel San Gimignano holiday apartment rental

                                                                    San Gimignano / Castel San Gimignano

                                                                    2 5 7 nights min

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

                                                                    from £84 / night

                                                                    £587 - £1,279 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 2 hours 29 minutes

                                                                    from £84 / night

                                                                      29

                                                                      Apartment rental in Castel San Gimignano with shared pool

                                                                      San Gimignano / Castel San Gimignano

                                                                      1 2 min stay varies

                                                                      • 1 bedroom
                                                                      • sleeps 2
                                                                      • min stay varies
                                                                      • Swimming pool
                                                                      • Child friendly
                                                                      • Air conditioning

                                                                      from £49 / night

                                                                      £337 - £884 / week

                                                                      Book View

                                                                      from £49 / night

                                                                        78

                                                                        Holiday b&b in Castel San Gimignano

                                                                        San Gimignano / Castel San Gimignano

                                                                        1 2 1 night min

                                                                        • 1 bedroom
                                                                        • sleeps 2
                                                                        • 1 night min
                                                                        • Pet friendly
                                                                        • Private garden

                                                                        from £90 / night

                                                                        £625 / week

                                                                        Book View

                                                                        from £90 / night

                                                                          25

                                                                          Apartment rental in Castel San Gimignano with shared pool

                                                                          San Gimignano / Castel San Gimignano

                                                                          3 6 min stay varies

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

                                                                          from £100 / night

                                                                          £447 - £844 / week

                                                                          Book View

                                                                          from £100 / night

                                                                            25

                                                                            Apartment rental in Castel San Gimignano with shared pool

                                                                            San Gimignano / Castel San Gimignano

                                                                            2 5 min stay varies

                                                                            • 2 bedrooms
                                                                            • sleeps 5
                                                                            • min stay varies
                                                                            • Swimming pool
                                                                            • Child friendly
                                                                            • Pet friendly

                                                                            from £100 / night

                                                                            £447 - £844 / week

                                                                            Book View

                                                                            from £100 / night

                                                                              30

                                                                              Apartment rental in Castel San Gimignano with shared pool

                                                                              San Gimignano / Castel San Gimignano

                                                                              3 5 min stay varies

                                                                              • 3 bedrooms
                                                                              • sleeps 5
                                                                              • min stay varies
                                                                              • Swimming pool

                                                                              from £100 / night

                                                                              £447 - £843 / week

                                                                              Book View

                                                                              from £100 / night

                                                                                24

                                                                                Holiday villa with swimming pool in Castel San Gimignano

                                                                                San Gimignano / Castel San Gimignano

                                                                                3 8 7 nights min

                                                                                • 3 bedrooms
                                                                                • sleeps 8
                                                                                • 7 nights min
                                                                                • Swimming pool
                                                                                • Child friendly
                                                                                • Ask about pets

                                                                                from £148 / night

                                                                                £1,032 - £2,023 / week

                                                                                Enquire View

                                                                                from £148 / night

                                                                                  23

                                                                                  Holiday villa rental

                                                                                  San Gimignano / Castel San Gimignano

                                                                                  3 6 7 nights min

                                                                                  • 3 bedrooms
                                                                                  • sleeps 6
                                                                                  • 7 nights min
                                                                                  • Swimming pool
                                                                                  • Child friendly
                                                                                  • Ask about pets

                                                                                  from £153 / night

                                                                                  £1,067 - £2,270 / week

                                                                                  Enquire View

                                                                                  from £153 / night

                                                                                  Top Destination reviews

                                                                                  Casa Gelsomino, ground floor, 2 bedrooms, private garden and shared pool
                                                                                  Great apartment. Fantastic Tuscan hospitality.

                                                                                  My wife and I chose Casa Gelsomino because we were travelling with our 18-month old daughter and wanted to be in a location with amenities within walking distance. The hamlet of Castel San Gimignano itself is a sleepy one but offers a great little convenience store (run by twin sisters) just across the road from the apartment, a nice bar (opposite) and a lovely restaurant offering a variety of Tuscan/Italian cuisine. As for the apartment, located on the ground floor (we were able to park our car directly outside the front door) with a spacious lounge diner and a compact but well-equipped kitchen neatly tucked away behind double sliding doors. Beyond that, a utility room with a washing machine, a decent family bathroom (shower cubicle but no bathtub) and two bedrooms; one with a king size bed the other with a day bed that converts into two singles or a double. We used this room for our daughter and Carlo (owner) provided a travel cot and bedding as well as a highchair. Free wifi was provided also offering speeds of around 12Mbps download and around 1 Mbps upload. Not bad considering it's in such a rural setting. By far the biggest positive for us was the outdoor space. Beautifully manicured lawns and flowerbeds leading down to the private pool and then the olive groves and cherry orchards beyond, all expertly and meticulously tended to by Carlo's mother Anna and father Renzo. It has to be said at this point that these lovely people were so warm and friendly and couldn't do enough to make our stay as comfortable and relaxing as possible. Anna even went as far as picking fresh herbs for me to use in my ragu and Renzo picked a load of cherries for us also. Whilst the pool was spotlessly clean (maintained by Carlo daily) it isn't heated, and whilst it was bearable for us adults, it was a little too cold for our daughter despite the ambient temperature being in the mid-30's centigrade. Plenty of sun loungers and the views across the valley are spectacular, particularly at sundown enjoying a glass or two of Chianti. All in all, we had a most enjoyable week here whilst exploring the surrounding areas including Siena, San Gimignano and Volterra to name a few. A car is recommended if staying for longer than a few days. One recommendation I would make, is for a welcome pack to be offered (even at a small charge) including basic sundries like salt, pepper, sugar, olive oil, milk etc. as the last thing you want to do after a long journey is then thinking about going to the supermarket, especially with a toddler :-) In summary, the apartment was great but the hospitality was superb! Tantissimi grazie Carlo, Emanuela, Anna e Renzo!see more
                                                                                  Casa Verbena, 3 bedrooms apartment, first floor, terrace
                                                                                  Perfect location with delightful owners

                                                                                  This is such a beautiful spot and ideal for exploring as very close to everything we wanted to see: Siena, San Gimignano, Volterra and many other less well known medieval towns and villages. The pool has a stunning view and is a perfect place to sunbathe, relax and read as well as cool off after a day's sightseeing. The owners couldn't have been more welcoming and their parents, who live on site, are completely charming. They brought us plums from their orchard and tried to help with our hopeless Italian. The only thing we missed in our upstairs, sleeps 6, appt was the opportunity to eat outside. To be fair, there is an outside eating area by the pool which we were told we could use but we felt uncomfortable about this as it belonged to the owners parents. That, however, is probably the fault of our own English reserve but it is the reason why I have given this a rating of 'Very Good' rather than 'Excellent'. The appartment was very comfortable, the location ideal for exploring and the owners completely charming and helpful.see more

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