Gaiole in Chianti apartment or villa with a private pool area | Holiday Lettings

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Filters applied: Private pool

1,321 Holiday homes

(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

    £315 / week

    Book View

    Responds fast!
    avg. 1 hour 19 minutes

    from £55 / 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 £112 / night

      £708 / week

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      from £112 / 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 £208 / night

        £1,455 - £2,425 / week

        Book View

        Responds fast!
        avg. 3 hours 56 minutes

        from £208 / 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

          £455 - £1,011 / week

          Book View

          Responds fast!
          avg. 27 minutes

          from £91 / 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 £527 / night

            £3,468 - £5,668 / week

            Book View

            Responds fast!
            avg. 3 hours 56 minutes

            from £527 / 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

              £354 - £920 / week

              Book View

              from £56 / night

                26

                Holiday villa with swimming pool in Gaiole in Chianti

                Province of Siena / Gaiole in Chianti

                4 12 min stay varies

                • 4 bedrooms
                • sleeps 12
                • min stay varies
                • Swimming pool
                • Child friendly
                • Pet friendly

                from £303 / night

                £2,121 / week

                Book View

                Responds fast!
                avg. 11 minutes

                from £303 / night

                  41

                  Gaiole in Chianti holiday home rental

                  Province of Siena / Gaiole in Chianti

                  5 13 min stay varies

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

                  from £390 / night

                  £2,731 - £4,827 / week

                  Book View

                  Responds fast!
                  avg. 2 hours 41 minutes

                  from £390 / night

                    36

                    Barbischio holiday home rental

                    Gaiole in Chianti / Barbischio

                    8 17 7 nights min

                    • 8 bedrooms
                    • sleeps 17
                    • 7 nights min
                    • Swimming pool
                    • Child friendly
                    • Pet friendly

                    from £196 / night

                    £1,375 - £5,407 / week

                    Book View

                    from £196 / night

                      22

                      Holiday home 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 £226 / night

                      £1,585 - £3,079 / week

                      Book View

                      from £226 / night

                        34

                        Holiday home with swimming pool in Castagnoli

                        Gaiole in Chianti / Castagnoli

                        4 9 min stay varies

                        • 4 bedrooms
                        • sleeps 9
                        • min stay varies
                        • Swimming pool
                        • Child friendly
                        • Pet friendly

                        from £200 / night

                        £1,402 - £3,172 / week

                        Book View

                        from £200 / 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
                          • Nearest beach 115 km
                          • Swimming pool
                          • Child friendly

                          from £682 / night

                          £4,768 - £6,349 / week

                          Book View

                          from £682 / night

                          (1) Excellent 

                            30

                            Villa rental in Gaiole in Chianti with swimming pool

                            Province of Siena / Gaiole in Chianti

                            7 14 7 nights min

                            • 7 bedrooms
                            • sleeps 14
                            • 7 nights min
                            • Nearest beach 100 km
                            • Swimming pool
                            • Child friendly

                            from £606 / night

                            £4,242 / week

                            Book View

                            from £606 / 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 £213 / night

                              £1,486 / week

                              Book View

                              from £213 / 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 £496 / night

                                £3,472 - £5,100 / week

                                Enquire View

                                from £496 / 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

                                    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

                                      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 £456 / night

                                      £2,881 - £3,841 / week

                                      Book View

                                      from £456 / 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 £462 / night

                                          £4,741 / week

                                          Book View

                                          from £462 / 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 £354 / night

                                            £2,474 - £3,926 / week

                                            Enquire View

                                            from £354 / 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 £1,261 / night

                                              £7,775 - £12,377 / week

                                              Book View

                                              from £1,261 / 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

                                                £566 / week

                                                Book View

                                                from £81 / 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 £132 / night

                                                  £919 / week

                                                  Book View

                                                  from £132 / 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 £175 / night

                                                    £1,221 - £2,803 / week

                                                    Enquire View

                                                    from £175 / 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

                                                        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

                                                          26

                                                          Holiday villa with swimming pool in Castagnoli

                                                          Gaiole in Chianti / Castagnoli

                                                          6 18 7 nights min

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

                                                          from £212 / night

                                                          £1,481 - £3,043 / week

                                                          Enquire View

                                                          from £212 / 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 £320 / night

                                                            £2,237 - £3,924 / week

                                                            Book View

                                                            from £320 / 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

                                                                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

                                                                  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 £364 / night

                                                                  £2,545 / week

                                                                  Book View

                                                                  from £364 / 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 £202 / night

                                                                    £1,414 - £3,247 / week

                                                                    Enquire View

                                                                    from £202 / night

                                                                      21

                                                                      Holiday villa 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
                                                                      • Air conditioning

                                                                      from £175 / night

                                                                      £1,224 - £2,131 / week

                                                                      Enquire View

                                                                      from £175 / 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 £351 / night

                                                                        £2,456 - £3,995 / week

                                                                        Enquire View

                                                                        from £351 / night

                                                                          32

                                                                          Gaiole in Chianti holiday villa rental

                                                                          Province of Siena / Gaiole in Chianti

                                                                          7 14 3 nights min

                                                                          • 7 bedrooms
                                                                          • sleeps 14
                                                                          • 3 nights min
                                                                          • Swimming pool
                                                                          • Child friendly

                                                                          from £1,248 / night

                                                                          £8,159 - £9,599 / week

                                                                          Book View

                                                                          from £1,248 / night

                                                                            24

                                                                            Gaiole in Chianti holiday villa rental

                                                                            Province of Siena / Gaiole in Chianti

                                                                            3 6 7 nights min

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

                                                                            from £308 / night

                                                                            £2,155 - £3,737 / week

                                                                            Enquire View

                                                                            from £308 / 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

                                                                                11

                                                                                Barbischio holiday villa rental

                                                                                Gaiole in Chianti / Barbischio

                                                                                3 6 min stay varies

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

                                                                                from £264 / night

                                                                                £1,846 / week

                                                                                Book View

                                                                                from £264 / night

                                                                                (1) Excellent 

                                                                                  31

                                                                                  Gaiole in Chianti holiday home rental

                                                                                  Province of Siena / Gaiole in Chianti

                                                                                  4 8 4 nights min

                                                                                  • 4 bedrooms
                                                                                  • sleeps 8
                                                                                  • 4 nights min
                                                                                  • Swimming pool
                                                                                  • Ask owner if suitable for children
                                                                                  • Air conditioning

                                                                                  from £546 / night

                                                                                  £3,330 - £4,891 / week

                                                                                  Book View

                                                                                  Responds fast!
                                                                                  avg. 48 minutes

                                                                                  from £546 / night

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