Family Friendly Holidays in Gaiole in Chianti - Holiday Lettings

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

Filters applied: Under 5s

5,040 family friendly properties

(6) Excellent 

    29

    Holiday apartment with shared pool in Gaiole in Chianti

    Province of Siena / Gaiole in Chianti

    2 6 7 nights min

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

    from £108 / night

    £753 - £1,099 / week

    Book View

    Responds fast!
    avg. 1 hour 40 minutes

    from £108 / night

    (7) Very Good 

      43

      Montefienali holiday home accommodation

      Gaiole in Chianti / Montefienali

      3 6 min stay varies

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

      from £55 / night

      £314 / week

      Book View

      Responds fast!
      avg. 1 hour 19 minutes

      from £55 / night

      (8) Excellent 

        20

        Apartment accommodation in Gaiole in Chianti with shared pool

        Province of Siena / Gaiole in Chianti

        2 6 2 nights min

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

        from £81 / night

        £573 / week

        Book View

        from £81 / night

        (14) Very Good 

          39

          Holiday villa with swimming pool, tennis court in Gaiole in Chianti

          Province of Siena / Gaiole in Chianti

          2 5 min stay varies

          • 2 bedrooms
          • sleeps 5
          • min stay varies
          • Nearest beach 110 km
          • Swimming pool
          • Child friendly

          from £206 / night

          £1,447 - £2,411 / week

          Book View

          Responds fast!
          avg. 3 hours 56 minutes

          from £206 / night

            7

            Holiday apartment in Gaiole in Chianti

            Province of Siena / Gaiole in Chianti

            2 6 3 nights min

            • 2 bedrooms
            • sleeps 6
            • 3 nights min
            • Child friendly
            • Pet friendly
            • Private garden

            from £136 / night

            £930 / week

            Book View

            from £136 / night

            (3) Excellent 

              28

              Gaiole in Chianti holiday barn let

              Province of Siena / Gaiole in Chianti

              2 4 2 nights min

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

              from £111 / night

              £704 / week

              Book View

              from £111 / night

              (14) Excellent 

                34

                Holiday apartment with shared pool in Gaiole in Chianti

                Province of Siena / Gaiole in Chianti

                3 8 min stay varies

                • 3 bedrooms
                • sleeps 8
                • min stay varies
                • Swimming pool
                • Child friendly
                • Air conditioning

                from £200 / night

                £1,200 - £1,600 / week

                Book View

                from £200 / night

                  29

                  Gaiole in Chianti holiday home rental

                  Province of Siena / Gaiole in Chianti

                  1 2 7 nights min

                  • 1 bedroom
                  • sleeps 2
                  • 7 nights min
                  • Swimming pool
                  • Child friendly
                  • Private garden

                  from £78 / night

                  £542 / week

                  Book View

                  from £78 / night

                    44

                    Holiday home with shared pool in Gaiole in Chianti

                    Province of Siena / Gaiole in Chianti

                    3 7 7 nights min

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

                    from £112 / night

                    £784 / week

                    Book View

                    from £112 / night

                      17

                      Nusenna holiday apartment rental

                      Gaiole in Chianti / Nusenna

                      2 5 min stay varies

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

                      from £81 / night

                      £562 / week

                      Book View

                      from £81 / night

                        6

                        Gaiole in Chianti holiday farmhouse rental

                        Province of Siena / Gaiole in Chianti

                        2 2 3 nights min

                        • 2 bedrooms
                        • sleeps 2
                        • 3 nights min
                        • Nearest beach 127 km
                        • Child friendly
                        • Pet friendly

                        from £86 / night

                        £573 / week

                        Book View

                        from £86 / night

                        (18) Excellent 

                          33

                          Holiday apartment with shared pool in Gaiole in Chianti

                          Province of Siena / Gaiole in Chianti

                          1 4 min stay varies

                          • 1 bedroom
                          • sleeps 4
                          • min stay varies
                          • Nearest beach 80 km
                          • Swimming pool
                          • Child friendly
                          “Comfort and relaxation in Chianti” We enjoyed everything about Casacorvo. The view from the terrace is still in our minds weeks after we returned. Those beautiful rolling hills and the view over to Barbischio. Great pool which, in September was very quiet. We visited Siena, Florence, San Gimignano, Arezzo andthe wine festival at Greve in Chianti. Nice local wine left by Phil was much appreciated. The facilities in the Borgo were great. Gaiole is lovely and friendly and you don't have to go far to find nice meals and bars.

                          from £125 / night

                          £575 - £775 / week

                          Book View

                          from £125 / night

                          (13) Excellent 

                            69

                            Holiday villa with swimming pool, tennis court in Gaiole in Chianti

                            Province of Siena / Gaiole in Chianti

                            4 10 min stay varies

                            • 4 bedrooms
                            • sleeps 10
                            • min stay varies
                            • Nearest beach 110 km
                            • Swimming pool
                            • Child friendly
                            “Excellent, spacious accommodation with a fantastic pool and view.” Very good, clear communication with the owner. Spacious, clean property Wonderful pool About 2 miles from villa to nearest village with bar, restaurant and small store Character property with high ceilings and lots of room Keeps cool indoors

                            from £523 / night

                            £3,445 - £5,631 / week

                            Book View

                            Responds fast!
                            avg. 3 hours 56 minutes

                            from £523 / night

                            (1) Excellent 

                              4

                              Holiday b&b in Gaiole in Chianti

                              Province of Siena / Gaiole in Chianti

                              1 2 1 night min

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

                              from £89 / night

                              £603 / week

                              Book View

                              from £89 / night

                              (4) Excellent 

                                21

                                Holiday villa rental

                                Province of Siena / Gaiole in Chianti

                                2 7 min stay varies

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

                                from £91 / night

                                £452 - £1,004 / week

                                Book View

                                Responds fast!
                                avg. 27 minutes

                                from £91 / night

                                  33

                                  Apartment rental in Gaiole in Chianti with shared pool

                                  Province of Siena / Gaiole in Chianti

                                  2 5 7 nights min

                                  • 2 bedrooms
                                  • sleeps 5
                                  • 7 nights min
                                  • Nearest beach 107 km
                                  • Swimming pool
                                  • Child friendly

                                  from £52 / night

                                  £360 - £781 / week

                                  Enquire View

                                  from £52 / night

                                    12

                                    Nusenna holiday home rental

                                    Gaiole in Chianti / Nusenna

                                    1 2 1 night min

                                    • 1 bedroom
                                    • sleeps 2
                                    • 1 night min
                                    • Swimming pool
                                    • Child friendly
                                    • Pet friendly

                                    from £86 / night

                                    £597 / week

                                    Book View

                                    from £86 / night

                                    (1) Excellent 

                                      20

                                      Gaiole in Chianti holiday apartment rental

                                      Province of Siena / Gaiole in Chianti

                                      1 3 7 nights min

                                      • 1 bedroom
                                      • sleeps 3
                                      • 7 nights min
                                      • Nearest beach 105 km
                                      • Swimming pool
                                      • Child friendly

                                      from £44 / night

                                      £307 - £648 / week

                                      Enquire View

                                      from £44 / night

                                        21

                                        Holiday apartment with shared pool in Gaiole in Chianti

                                        Province of Siena / Gaiole in Chianti

                                        2 5 3 nights min

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

                                        from £106 / night

                                        £623 - £894 / week

                                        Book View

                                        Responds fast!
                                        avg. 2 hours 47 minutes

                                        from £106 / night

                                          18

                                          Gaiole in Chianti holiday condo rental

                                          Province of Siena / Gaiole in Chianti

                                          3 5 1 night min

                                          • 3 bedrooms
                                          • sleeps 5
                                          • 1 night min
                                          • Child friendly
                                          • Pet friendly
                                          • Private garden

                                          from £56 / night

                                          £362 / week

                                          Book View

                                          from £56 / night

                                            21

                                            Holiday guest house in Montefienali

                                            Gaiole in Chianti / Montefienali

                                            2 6 min stay varies

                                            • 2 bedrooms
                                            • sleeps 6
                                            • min stay varies
                                            • Child friendly
                                            • Ask about pets
                                            • Private garden

                                            from £55 / night

                                            £352 / week

                                            Book View

                                            Responds fast!
                                            avg. 1 hour 19 minutes

                                            from £55 / night

                                              29

                                              Gaiole in Chianti holiday apartment rental

                                              Province of Siena / Gaiole in Chianti

                                              4 8 3 nights min

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

                                              from £181 / night

                                              £1,135 - £1,376 / week

                                              Book View

                                              Responds fast!
                                              avg. 2 hours 47 minutes

                                              from £181 / night

                                                25

                                                Apartment rental in Gaiole in Chianti with shared pool, golf nearby

                                                Province of Siena / Gaiole in Chianti

                                                2 5 7 nights min

                                                • 2 bedrooms
                                                • sleeps 5
                                                • 7 nights min
                                                • Nearest beach 107 km
                                                • Swimming pool
                                                • Child friendly

                                                from £52 / night

                                                £360 - £781 / week

                                                Enquire View

                                                from £52 / night

                                                  23

                                                  Holiday apartment with shared pool in Gaiole in Chianti

                                                  Province of Siena / Gaiole in Chianti

                                                  2 5 min stay varies

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

                                                  from £126 / night

                                                  £623 - £894 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 2 hours 50 minutes

                                                  from £126 / night

                                                    33

                                                    Gaiole in Chianti holiday apartment rental

                                                    Province of Siena / Gaiole in Chianti

                                                    2 5 7 nights min

                                                    • 2 bedrooms
                                                    • sleeps 5
                                                    • 7 nights min
                                                    • Nearest beach 107 km
                                                    • Swimming pool
                                                    • Child friendly

                                                    from £52 / night

                                                    £360 - £781 / week

                                                    Enquire View

                                                    from £52 / night

                                                      24

                                                      Holiday apartment with shared pool in Gaiole in Chianti

                                                      Province of Siena / Gaiole in Chianti

                                                      1 3 7 nights min

                                                      • 1 bedroom
                                                      • sleeps 3
                                                      • 7 nights min
                                                      • Nearest beach 105 km
                                                      • Swimming pool
                                                      • Child friendly

                                                      from £39 / night

                                                      £268 - £636 / week

                                                      Enquire View

                                                      from £39 / night

                                                      (3) Average 

                                                        12

                                                        Holiday apartment with shared pool in Gaiole in Chianti

                                                        Province of Siena / Gaiole in Chianti

                                                        1 2 7 nights min

                                                        • 1 bedroom
                                                        • sleeps 2
                                                        • 7 nights min
                                                        • Swimming pool
                                                        • Child friendly
                                                        • Pet friendly

                                                        from £85 / night

                                                        £593 / week

                                                        Book View

                                                        from £85 / night

                                                        (1) Excellent 

                                                          62

                                                          Holiday villa in Gaiole in Chianti

                                                          Province of Siena / Gaiole in Chianti

                                                          5 10 7 nights min

                                                          • 5 bedrooms
                                                          • sleeps 10
                                                          • 7 nights min
                                                          • Child friendly
                                                          • Pet friendly

                                                          from £474 / night

                                                          £3,313 / week

                                                          Book View

                                                          from £474 / night

                                                          (2) Very Good 

                                                            13

                                                            Holiday apartment with swimming pool in Gaiole in Chianti

                                                            Province of Siena / Gaiole in Chianti

                                                            2 4 2 nights min

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

                                                            from £56 / night

                                                            £352 - £914 / week

                                                            Book View

                                                            from £56 / night

                                                              16

                                                              Holiday apartment with shared pool in Nusenna

                                                              Gaiole in Chianti / Nusenna

                                                              2 4 min stay varies

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

                                                              from £71 / night

                                                              £493 / week

                                                              Book View

                                                              from £71 / night

                                                                13

                                                                Nusenna holiday apartment rental

                                                                Gaiole in Chianti / Nusenna

                                                                2 5 min stay varies

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

                                                                from £91 / night

                                                                £633 / week

                                                                Book View

                                                                from £91 / night

                                                                  32

                                                                  Holiday apartment with shared pool in Gaiole in Chianti

                                                                  Province of Siena / Gaiole in Chianti

                                                                  1 4 7 nights min

                                                                  • 1 bedroom
                                                                  • sleeps 4
                                                                  • 7 nights min
                                                                  • Nearest beach 105 km
                                                                  • Swimming pool
                                                                  • Child friendly

                                                                  from £49 / night

                                                                  £342 - £868 / week

                                                                  Enquire View

                                                                  from £49 / night

                                                                  (1) Very Good 

                                                                    15

                                                                    Gaiole in Chianti holiday home rental

                                                                    Province of Siena / Gaiole in Chianti

                                                                    2 6 2 nights min

                                                                    • 2 bedrooms
                                                                    • sleeps 6
                                                                    • 2 nights min
                                                                    • Child friendly

                                                                    from £76 / night

                                                                    £483 - £651 / week

                                                                    Book View

                                                                    from £76 / night

                                                                      18

                                                                      Gaiole in Chianti holiday apartment rental

                                                                      Province of Siena / Gaiole in Chianti

                                                                      2 5 7 nights min

                                                                      • 2 bedrooms
                                                                      • sleeps 5
                                                                      • 7 nights min
                                                                      • Nearest beach 107 km
                                                                      • Swimming pool
                                                                      • Child friendly

                                                                      from £52 / night

                                                                      £360 - £781 / week

                                                                      Enquire View

                                                                      from £52 / night

                                                                        24

                                                                        Holiday apartment with shared pool in Gaiole in Chianti

                                                                        Province of Siena / Gaiole in Chianti

                                                                        2 4 7 nights min

                                                                        • 2 bedrooms
                                                                        • sleeps 4
                                                                        • 7 nights min
                                                                        • Nearest beach 125 km
                                                                        • Swimming pool
                                                                        • Child friendly

                                                                        from £79 / night

                                                                        £553 - £1,145 / week

                                                                        Enquire View

                                                                        from £79 / night

                                                                        (1) Excellent 

                                                                          24

                                                                          Holiday apartment with shared pool in Gaiole in Chianti

                                                                          Province of Siena / Gaiole in Chianti

                                                                          4 10 min stay varies

                                                                          • 4 bedrooms
                                                                          • sleeps 10
                                                                          • min stay varies
                                                                          • Nearest beach 80 km
                                                                          • Swimming pool
                                                                          • Child friendly

                                                                          from £350 / night

                                                                          £2,000 - £2,400 / week

                                                                          Book View

                                                                          from £350 / night

                                                                            15

                                                                            Gaiole in Chianti holiday farmhouse rental

                                                                            Province of Siena / Gaiole in Chianti

                                                                            9 22 1 night min

                                                                            • 9 bedrooms
                                                                            • sleeps 22
                                                                            • 1 night min
                                                                            • Child friendly
                                                                            • Private garden

                                                                            from £77 / night

                                                                            £502 - £5,842 / week

                                                                            Book View

                                                                            from £77 / night

                                                                              47

                                                                              Gaiole in Chianti holiday apartment rental

                                                                              Province of Siena / Gaiole in Chianti

                                                                              2 4 7 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 4
                                                                              • 7 nights min
                                                                              • Nearest beach 100 km
                                                                              • Child friendly
                                                                              • Private garden

                                                                              from £141 / night

                                                                              £984 / week

                                                                              Book View

                                                                              from £141 / night

                                                                                25

                                                                                Holiday apartment with shared pool in Gaiole in Chianti

                                                                                Province of Siena / Gaiole in Chianti

                                                                                1 4 7 nights min

                                                                                • 1 bedroom
                                                                                • sleeps 4
                                                                                • 7 nights min
                                                                                • Swimming pool
                                                                                • Child friendly
                                                                                • Air conditioning

                                                                                from £66 / night

                                                                                £218 - £906 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 1 hour 21 minutes

                                                                                from £66 / night

                                                                                  28

                                                                                  Apartment letting in Gaiole in Chianti with shared pool

                                                                                  Province of Siena / Gaiole in Chianti

                                                                                  2 4 min stay varies

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

                                                                                  from £52 / night

                                                                                  £360 - £844 / week

                                                                                  Book View

                                                                                  Responds fast!
                                                                                  avg. 2 hours 19 minutes

                                                                                  from £52 / night

                                                                                  Also consider