Apartments in Gaiole in Chianti and Villas – Holiday Lettings - Holiday Rentals Gaiole in Chianti

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5,765 Holiday homes

    20

    Gaiole in Chianti holiday home rental

    Province of Siena / Gaiole in Chianti

    2 4 7 nights min

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

    from £111 / night

    £774 / week

    Book View

    from £111 / night

      15

      Apartment rental in Gaiole in Chianti with shared pool

      Province of Siena / Gaiole in Chianti

      1 4 1 night min

      • 1 bedroom
      • sleeps 4
      • 1 night min
      • Nearest beach 100 km
      • Swimming pool
      • Child friendly

      from £95 / night

      £616 / week

      Book View

      from £95 / night

        26

        Home accommodation in Gaiole in Chianti

        Province of Siena / Gaiole in Chianti

        1 2 2 nights min

        • 1 bedroom
        • sleeps 2
        • 2 nights min
        • Child friendly
        • Pet friendly

        from £70 / night

        £650 / week

        Book View

        from £70 / night

          32

          Holiday apartment with shared pool in Gaiole in Chianti

          Province of Siena / Gaiole in Chianti

          4 7 min stay varies

          • 4 bedrooms
          • sleeps 7
          • min stay varies
          • Swimming pool
          • Child friendly

          from £262 / night

          £1,660 - £1,969 / week

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          from £262 / night

            38

            Gaiole in Chianti holiday apartment rental

            Province of Siena / Gaiole in Chianti

            4 6 min stay varies

            • 4 bedrooms
            • sleeps 6
            • min stay varies
            • Swimming pool
            • Child friendly

            from £284 / night

            £1,822 - £2,110 / week

            Book View

            from £284 / night

              23

              Holiday home with shared pool in Gaiole in Chianti

              Province of Siena / Gaiole in Chianti

              3 6 2 nights min

              • 3 bedrooms
              • sleeps 6
              • 2 nights min
              • Swimming pool
              • Ask owner if suitable for children
              • Air conditioning

              from £162 / night

              £984 - £1,759 / week

              Book View

              Responds fast!
              avg. 48 minutes

              from £162 / night

                47

                Holiday villa with swimming pool in Gaiole in Chianti

                Province of Siena / Gaiole in Chianti

                4 8 7 nights min

                • 4 bedrooms
                • sleeps 8
                • 7 nights min
                • Swimming pool
                • Child friendly
                • Air conditioning

                from £489 / night

                £3,421 - £5,024 / week

                Enquire View

                from £489 / night

                  37

                  Holiday home rental

                  Province of Siena / Gaiole in Chianti

                  5 10 5 nights min

                  • 5 bedrooms
                  • sleeps 10
                  • 5 nights min
                  • Nearest beach 124 km
                  • Swimming pool
                  • Child friendly

                  from £211 / night

                  £1,474 / week

                  Book View

                  from £211 / night

                    25

                    Holiday apartment rental

                    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 £181 / night

                    £1,266 / week

                    Book View

                    from £181 / night

                      30

                      Holiday villa with swimming pool in Gaiole in Chianti

                      Province of Siena / Gaiole in Chianti

                      6 12 4 nights min

                      • 6 bedrooms
                      • sleeps 12
                      • 4 nights min
                      • Swimming pool
                      • Child friendly
                      • Air conditioning

                      from £453 / night

                      £2,864 - £3,818 / week

                      Book View

                      Responds fast!
                      avg. 2 hours 52 minutes

                      from £453 / night

                        75

                        Villa rental in Gaiole in Chianti with swimming pool

                        Province of Siena / Gaiole in Chianti

                        31 50 7 nights min

                        • 31 bedrooms
                        • sleeps 50
                        • 7 nights min
                        • Swimming pool
                        • Child friendly
                        • Pet friendly

                        from £3,203 / night

                        £22,419 - £32,423 / week

                        Enquire View

                        from £3,203 / night

                          13

                          Holiday apartment in Gaiole in Chianti

                          Province of Siena / Gaiole in Chianti

                          2 4 2 nights min

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

                          from £190 / night

                          £1,330 / week

                          Book View

                          from £190 / night

                            36

                            Holiday villa with swimming pool in Gaiole in Chianti

                            Province of Siena / Gaiole in Chianti

                            4 8 7 nights min

                            • 4 bedrooms
                            • sleeps 8
                            • 7 nights min
                            • Swimming pool
                            • Child friendly
                            • Air conditioning

                            from £496 / night

                            £3,472 - £5,100 / week

                            Enquire View

                            from £496 / night

                              18

                              Holiday apartment in Gaiole in Chianti

                              Province of Siena / Gaiole in Chianti

                              3 9 1 night min

                              • 3 bedrooms
                              • sleeps 9
                              • 1 night min
                              • Child friendly
                              • Ask about pets

                              from £299 / night

                              £1,658 / week

                              Book View

                              from £299 / night

                              (2) Excellent 

                                18

                                Gaiole in Chianti holiday b&b rental

                                Province of Siena / Gaiole in Chianti

                                1 2 min stay varies

                                • 1 bedroom
                                • sleeps 2
                                • min stay varies
                                • Nearest beach 75 km
                                • Child friendly
                                • Private garden

                                from £110 / night

                                £770 - £1,300 / week

                                Book View

                                from £110 / night

                                  14

                                  Gaiole in Chianti holiday home rental

                                  Province of Siena / Gaiole in Chianti

                                  2 6 min stay varies

                                  • 2 bedrooms
                                  • sleeps 6
                                  • min stay varies
                                  • Nearest beach 109 km
                                  • Swimming pool
                                  • Child friendly

                                  from £71 / night

                                  £492 - £1,755 / week

                                  Book View

                                  from £71 / night

                                    24

                                    Holiday villa with swimming pool in Gaiole in Chianti

                                    Province of Siena / Gaiole in Chianti

                                    4 2 7 nights min

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

                                    from £318 / night

                                    £2,224 - £3,902 / week

                                    Book View

                                    Responds fast!
                                    avg. 2 hours 52 minutes

                                    from £318 / night

                                      26

                                      Holiday villa in Gaiole in Chianti

                                      Province of Siena / Gaiole in Chianti

                                      6 18 7 nights min

                                      • 6 bedrooms
                                      • sleeps 18
                                      • 7 nights min
                                      • Swimming pool
                                      • Child friendly
                                      • Pet friendly

                                      from £234 / night

                                      £1,635 - £3,356 / week

                                      Enquire View

                                      from £234 / night

                                        42

                                        Holiday home with swimming pool in Gaiole in Chianti

                                        Province of Siena / Gaiole in Chianti

                                        4 8 min stay varies

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

                                        from £459 / night

                                        £4,718 / week

                                        Book View

                                        from £459 / night

                                          21

                                          Holiday villa rental

                                          Province of Siena / Gaiole in Chianti

                                          5 10 7 nights min

                                          • 5 bedrooms
                                          • sleeps 10
                                          • 7 nights min
                                          • Swimming pool
                                          • Child friendly
                                          • Ask about pets

                                          from £348 / night

                                          £2,434 - £3,863 / week

                                          Enquire View

                                          from £348 / night

                                            33

                                            Holiday villa with swimming pool in Gaiole in Chianti

                                            Province of Siena / Gaiole in Chianti

                                            4 8 7 nights min

                                            • 4 bedrooms
                                            • sleeps 8
                                            • 7 nights min
                                            • Swimming pool
                                            • Child friendly
                                            • Air conditioning

                                            from £308 / night

                                            £2,153 - £4,150 / week

                                            Enquire View

                                            from £308 / night

                                              13

                                              Villa rental in Gaiole in Chianti with swimming pool

                                              Province of Siena / Gaiole in Chianti

                                              5 13 min stay varies

                                              • 5 bedrooms
                                              • sleeps 13
                                              • min stay varies
                                              • Swimming pool
                                              • Child friendly

                                              from £361 / night

                                              £2,527 / week

                                              Book View

                                              from £361 / night

                                                5

                                                Holiday apartment with shared pool in Nusenna

                                                Gaiole in Chianti / Nusenna

                                                2 5 2 nights min

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

                                                from £116 / night

                                                £807 / week

                                                Book View

                                                from £116 / night

                                                  28

                                                  Holiday villa rental

                                                  Province of Siena / Gaiole in Chianti

                                                  2 12 7 nights min

                                                  • 2 bedrooms
                                                  • sleeps 12
                                                  • 7 nights min
                                                  • Swimming pool
                                                  • Child friendly
                                                  • Air conditioning

                                                  from £876 / night

                                                  £6,130 - £7,690 / week

                                                  Enquire View

                                                  from £876 / night

                                                    11

                                                    Barbischio holiday villa rental

                                                    Gaiole in Chianti / Barbischio

                                                    3 6 7 nights min

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

                                                    from £349 / night

                                                    £2,443 - £3,975 / week

                                                    Enquire View

                                                    from £349 / night

                                                      21

                                                      Holiday home with swimming pool in Nusenna

                                                      Gaiole in Chianti / Nusenna

                                                      1 4 min stay varies

                                                      • 1 bedroom
                                                      • sleeps 4
                                                      • min stay varies
                                                      • Swimming pool
                                                      • Child friendly
                                                      • Pet friendly

                                                      from £81 / night

                                                      £562 / week

                                                      Book View

                                                      from £81 / night

                                                        7

                                                        Holiday apartment with shared pool in Nusenna

                                                        Gaiole in Chianti / Nusenna

                                                        2 4 2 nights min

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

                                                        from £102 / night

                                                        £714 / week

                                                        Book View

                                                        from £102 / night

                                                          33

                                                          Holiday villa with swimming pool in Gaiole in Chianti

                                                          Province of Siena / Gaiole in Chianti

                                                          4 8 7 nights min

                                                          • 4 bedrooms
                                                          • sleeps 8
                                                          • 7 nights min
                                                          • Swimming pool
                                                          • Child friendly
                                                          • Air conditioning

                                                          from £734 / night

                                                          £5,132 - £7,790 / week

                                                          Enquire View

                                                          from £734 / night

                                                            23

                                                            Holiday home in Gaiole in Chianti

                                                            Province of Siena / Gaiole in Chianti

                                                            3 6 4 nights min

                                                            • 3 bedrooms
                                                            • sleeps 6
                                                            • 4 nights min
                                                            • Swimming pool
                                                            • Ask owner if suitable for children
                                                            • Air conditioning

                                                            from £162 / night

                                                            £984 - £1,759 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 48 minutes

                                                            from £162 / night

                                                              23

                                                              Holiday villa with swimming pool in Barbischio

                                                              Gaiole in Chianti / Barbischio

                                                              4 8 7 nights min

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

                                                              from £203 / night

                                                              £1,415 - £2,954 / week

                                                              Enquire View

                                                              from £203 / night

                                                                9

                                                                Holiday apartment in Gaiole in Chianti

                                                                Province of Siena / Gaiole in Chianti

                                                                2 5 3 nights min

                                                                • 2 bedrooms
                                                                • sleeps 5
                                                                • 3 nights min
                                                                • Child friendly

                                                                from £131 / night

                                                                £913 / week

                                                                Book View

                                                                from £131 / night

                                                                  41

                                                                  Holiday villa with swimming pool in Gaiole in Chianti

                                                                  Province of Siena / Gaiole in Chianti

                                                                  5 13 7 nights min

                                                                  • 5 bedrooms
                                                                  • sleeps 13
                                                                  • 7 nights min
                                                                  • Swimming pool
                                                                  • Child friendly
                                                                  • Ask about pets

                                                                  from £343 / night

                                                                  £2,399 - £4,667 / week

                                                                  Enquire View

                                                                  from £343 / night

                                                                    23

                                                                    Holiday villa with swimming pool in Barbischio

                                                                    Gaiole in Chianti / Barbischio

                                                                    4 8 7 nights min

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

                                                                    from £184 / night

                                                                    £1,283 - £2,946 / week

                                                                    Enquire View

                                                                    from £184 / night

                                                                      22

                                                                      Holiday manor house with swimming pool in Barbischio

                                                                      Gaiole in Chianti / Barbischio

                                                                      2 5 3 nights min

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

                                                                      from £131 / night

                                                                      £913 / week

                                                                      Book View

                                                                      from £131 / night

                                                                        28

                                                                        Villa letting in Gaiole in Chianti with swimming pool

                                                                        Province of Siena / Gaiole in Chianti

                                                                        4 8 7 nights min

                                                                        • 4 bedrooms
                                                                        • sleeps 8
                                                                        • 7 nights min
                                                                        • Swimming pool
                                                                        • Child friendly
                                                                        • Air conditioning

                                                                        from £538 / night

                                                                        £3,762 - £5,085 / week

                                                                        Enquire View

                                                                        from £538 / night

                                                                          27

                                                                          Holiday apartment with shared pool in Gaiole in Chianti

                                                                          Province of Siena / Gaiole in Chianti

                                                                          3 5 min stay varies

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

                                                                          from £221 / night

                                                                          £1,365 - £1,618 / week

                                                                          Book View

                                                                          from £221 / night

                                                                          (30) Excellent 

                                                                            71

                                                                            Holiday villa in Gaiole in Chianti

                                                                            Province of Siena / Gaiole in Chianti

                                                                            5 13 min stay varies

                                                                            • 5 bedrooms
                                                                            • sleeps 13
                                                                            • min stay varies
                                                                            • Nearest beach 40 km
                                                                            • Swimming pool
                                                                            • Child friendly
                                                                            “Idyllic stay in very comfortable, beautifully furnished house” Driving up to La Pratola you get a great view of the house as you climb the hill to it, but nothing could have prepared us for the amazing view back down the hill and across the valley from the infinity pool. Breathtaking. We were supplied with amazing food and service by a really sweet lady who looked after us well, whilst also discretely blending in, never making us feel self-conscious, and the maid service was excellent. Nearby Gaiole has all you could need, and is pretty, but Florence and Siena are wonderfully close by for a day trip. There are good walks and bike rides ( or runs) straight out from the house, but we just wanted to chill out by the pool or in the lovely courtyard most of the time. The Interior is very comfortably furnished to a high standard, with plenty of places for people to relax, so if you are in a big group it works well to go off and do you own thing for a while - the upstairs living room is great- huge squishy leather sofas and a big screen TV. We particularly enjoyed the pool table too. We weren't disappointed by La Pratola and would happily go back there again.

                                                                            from £1,248 / night

                                                                            £7,695 - £12,249 / week

                                                                            Book View

                                                                            from £1,248 / night

                                                                            (2) Excellent 

                                                                              21

                                                                              Holiday home with shared pool in Gaiole in Chianti

                                                                              Province of Siena / Gaiole in Chianti

                                                                              2 5 6 nights min

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

                                                                              from £151 / night

                                                                              £978 / week

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                                                                              from £151 / night

                                                                                8

                                                                                Holiday apartment in Gaiole in Chianti

                                                                                Province of Siena / Gaiole in Chianti

                                                                                1 4 3 nights min

                                                                                • 1 bedroom
                                                                                • sleeps 4
                                                                                • 3 nights min
                                                                                • Child friendly

                                                                                from £91 / night

                                                                                £632 / week

                                                                                Book View

                                                                                from £91 / night

                                                                                  48

                                                                                  Nusenna holiday villa rental

                                                                                  Gaiole in Chianti / Nusenna

                                                                                  5 10 3 nights min

                                                                                  • 5 bedrooms
                                                                                  • sleeps 10
                                                                                  • 3 nights min
                                                                                  • Child friendly
                                                                                  • Private garden

                                                                                  from £358 / night

                                                                                  £2,504 - £3,045 / week

                                                                                  Book View

                                                                                  from £358 / night

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