Horse Riding Holiday Accommodation in Gaiole in Chianti - Holiday Lettings

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1,066 properties with horse riding on site or nearby

(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

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    from £81 / 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

      (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 £207 / night

        £1,452 - £2,419 / week

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        Responds fast!
        avg. 3 hours 56 minutes

        from £207 / 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 £526 / night

          £3,459 - £5,655 / week

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          Responds fast!
          avg. 3 hours 56 minutes

          from £526 / night

          (2) Average 

            23

            Lecchi holiday apartment rental

            Gaiole in Chianti / Lecchi

            2 5 min stay varies

            • 2 bedrooms
            • sleeps 5
            • min stay varies
            • Swimming pool
            • Suitable for children age 5+
            • Pet friendly

            from £81 / night

            £474 - £706 / week

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            Responds fast!
            avg. 2 hours 19 minutes

            from £81 / 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

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              from £125 / 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

                £308 - £651 / week

                Enquire View

                from £44 / night

                  24

                  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
                  • Nearest beach 105 km
                  • Swimming pool
                  • Suitable for children age 5+

                  from £51 / night

                  £352 - £808 / week

                  Enquire View

                  from £51 / 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

                      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

                      £361 - £784 / week

                      Enquire View

                      from £52 / 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

                        £344 - £872 / week

                        Enquire View

                        from £49 / 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

                          £595 / week

                          Book View

                          from £85 / 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

                            £363 / week

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                            from £56 / night

                            (41) Excellent 

                              24

                              Gaiole in Chianti holiday apartment accommodation

                              Province of Siena / Gaiole in Chianti

                              1 2 min stay varies

                              • 1 bedroom
                              • sleeps 2
                              • min stay varies
                              • Swimming pool
                              • Air conditioning
                              • Private garden
                              “Fantastic stay in a beautiful setting” Have just returned from a week stay in Gaiole in Chianti following l'eroica and everything you hear and read about the region is true - it really is idyllic and a perfect place to relax, visit local villages, cycle or walk around. Siena, which is equally stunning, is also barely 30 minutes away. The apartment is perfectly located with stunning views overlooking the village - it was great to sit out in the private garden in the morning and at sunset and just relax. However this wasn't at the expense of being away from the centre of the village and the amenities - it was not even a 5 minute walk to the deli, butcher etc. (and only 3 minutes to the local takeaway pizza - I timed it!). The apartment itself is very well appointed with seemingly everything thought of - there were even umbrellas that we could use when there was rain one morning. The 'borgo' also has a swimming pool and gym as well as plenty of parking nearby. From the initial booking, John and Tracy made everything very easy and the service was simple and hassle free. - we'd definitely go again!

                              from £103 / night

                              £722 / week

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                              Responds fast!
                              avg. 1 hour 19 minutes

                              from £103 / 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

                                £353 - £918 / week

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                                from £56 / night

                                (1) Average 

                                  25

                                  Lecchi holiday apartment rental

                                  Gaiole in Chianti / Lecchi

                                  2 5 3 nights min

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

                                  from £91 / night

                                  £552 - £783 / week

                                  Book View

                                  Responds fast!
                                  avg. 2 hours 50 minutes

                                  from £91 / 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

                                    £269 - £639 / week

                                    Enquire View

                                    from £39 / 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

                                      £361 - £784 / week

                                      Enquire View

                                      from £52 / 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

                                        £484 - £653 / 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

                                          £361 - £784 / week

                                          Enquire View

                                          from £52 / 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

                                            £3,316 / week

                                            Book View

                                            from £474 / 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

                                                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 £80 / night

                                                £555 - £1,149 / week

                                                Enquire View

                                                from £80 / 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 £142 / night

                                                  £988 / week

                                                  Book View

                                                  from £142 / night

                                                    31

                                                    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
                                                    • Swimming pool
                                                    • Child friendly
                                                    • Air conditioning

                                                    from £52 / night

                                                    £360 - £843 / week

                                                    Enquire View

                                                    from £52 / night

                                                    (3) Very Good 

                                                      33

                                                      Holiday villa with shared pool in Gaiole in Chianti

                                                      Province of Siena / Gaiole in Chianti

                                                      3 8 7 nights min

                                                      • 3 bedrooms
                                                      • sleeps 8
                                                      • 7 nights min
                                                      • Nearest beach 107 km
                                                      • Swimming pool
                                                      • Child friendly

                                                      from £95 / night

                                                      £661 - £1,326 / week

                                                      Enquire View

                                                      from £95 / 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

                                                        £618 / week

                                                        Book View

                                                        from £95 / night

                                                          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

                                                            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 £71 / night

                                                            £653 / week

                                                            Book View

                                                            from £71 / 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 £1,254 / night

                                                              £7,732 - £12,308 / week

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                                                              from £1,254 / 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 £152 / night

                                                                £983 / week

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                                                                from £152 / night

                                                                Great rentals within 20 miles that match your search

                                                                Distance approx 12.25 miles from Gaiole in Chianti

                                                                (1) Excellent 

                                                                  16

                                                                  Pergine Valdarno holiday apartment rental

                                                                  Province of Arezzo / Pergine Valdarno

                                                                  4 10 min stay varies

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

                                                                  Pricing unknown

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                                                                  Pricing unknown

                                                                  Distance approx 3.43 miles from Gaiole in Chianti Show on Map

                                                                    32

                                                                    Lecchi in Chianti holiday home rental

                                                                    Province of Siena / Lecchi in Chianti

                                                                    2 4 7 nights min

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

                                                                    from £142 / night

                                                                    £990 / week

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                                                                    from £142 / night

                                                                    Distance approx 16.66 miles from Gaiole in Chianti

                                                                      28

                                                                      Holiday villa with swimming pool in Asciano

                                                                      Province of Siena / Asciano

                                                                      4 10 2 nights min

                                                                      • 4 bedrooms
                                                                      • sleeps 10
                                                                      • 2 nights min
                                                                      • Nearest beach 100 km
                                                                      • Swimming pool
                                                                      • Child friendly

                                                                      from £301 / night

                                                                      £2,106 / week

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                                                                      Responds fast!
                                                                      avg. 3 hours 38 minutes

                                                                      from £301 / night

                                                                      Distance approx 16.81 miles from Gaiole in Chianti

                                                                      (16) Very Good 

                                                                        46

                                                                        Holiday hotel apartment in Impruneta

                                                                        Province of Florence / Impruneta

                                                                        1 4 3 nights min

                                                                        • 1 bedroom
                                                                        • sleeps 4
                                                                        • 3 nights min
                                                                        • Child friendly
                                                                        • Car not necessary
                                                                        • Pet friendly

                                                                        from £60 / night

                                                                        £394 - £531 / week

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                                                                        from £60 / night

                                                                        Distance approx 12.15 miles from Gaiole in Chianti

                                                                          12

                                                                          Holiday apartment with shared pool in Castelfranco di Sopra

                                                                          Castelfranco Piandisco / Castelfranco di Sopra

                                                                          1 2 1 night min

                                                                          • 1 bedroom
                                                                          • sleeps 2
                                                                          • 1 night min
                                                                          • Swimming pool
                                                                          • Private garden

                                                                          from £71 / night

                                                                          £553 / week

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                                                                          from £71 / night

                                                                          Distance approx 11.21 miles from Gaiole in Chianti Show on Map

                                                                            19

                                                                            Holiday apartment rental

                                                                            Province of Siena / Castelnuovo Berardenga

                                                                            1 4 1 night min

                                                                            • 1 bedroom
                                                                            • sleeps 4
                                                                            • 1 night min
                                                                            • Beach / lakeside relaxation
                                                                            • Nearest beach 120 km
                                                                            • Child friendly

                                                                            from £81 / night

                                                                            £493 / week

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                                                                            Responds fast!
                                                                            avg. 28 minutes

                                                                            from £81 / night

                                                                            Distance approx 18.9 miles from Gaiole in Chianti

                                                                            (23) Excellent 

                                                                              7

                                                                              Holiday apartment in Rosia

                                                                              Province of Siena / Rosia

                                                                              1 4 1 night min

                                                                              • 1 bedroom
                                                                              • sleeps 4
                                                                              • 1 night min
                                                                              • Child friendly
                                                                              • Pet friendly

                                                                              from £75 / night

                                                                              £412 / week

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                                                                              from £75 / night

                                                                              Distance approx 13.16 miles from Gaiole in Chianti

                                                                              (4) Excellent 

                                                                                14

                                                                                Holiday apartment in Greve in Chianti

                                                                                Province of Florence / Greve in Chianti

                                                                                2 4 min stay varies

                                                                                • 2 bedrooms
                                                                                • sleeps 4
                                                                                • min stay varies
                                                                                • Child friendly
                                                                                • Air conditioning
                                                                                • Ask about pets

                                                                                Pricing unknown

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                                                                                Pricing unknown

                                                                                Distance approx 15.96 miles from Gaiole in Chianti

                                                                                  27

                                                                                  Holiday villa with swimming pool in San Casciano in Val di Pesa

                                                                                  Province of Florence / San Casciano in Val di Pesa

                                                                                  11 15 7 nights min

                                                                                  • 11 bedrooms
                                                                                  • sleeps 15
                                                                                  • 7 nights min
                                                                                  • Nearest beach 120 km
                                                                                  • Swimming pool
                                                                                  • Child friendly

                                                                                  from £990 / night

                                                                                  £6,931 - £8,246 / week

                                                                                  Enquire View

                                                                                  from £990 / night

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