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

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5,691 Holiday homes

(6) Excellent 

    29

    Holiday apartment with shared pool in Gaiole in Chianti

    Province of Siena / Gaiole in Chianti

    2 6 7 nights min

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

    from £106 / night

    £743 - £1,084 / week

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    Responds fast!
    avg. 1 hour 40 minutes

    from £106 / night

    (7) Very Good 

      43

      Montefienali holiday home accommodation

      Gaiole in Chianti / Montefienali

      3 6 min stay varies

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

      from £54 / night

      £309 / week

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      Responds fast!
      avg. 1 hour 19 minutes

      from £54 / 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 £109 / night

        £693 / week

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        from £109 / night

          7

          Holiday apartment in Gaiole in Chianti

          Province of Siena / Gaiole in Chianti

          2 6 3 nights min

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

          from £134 / night

          £915 / week

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          from £134 / night

          (8) Excellent 

            20

            Apartment accommodation in Gaiole in Chianti with shared pool

            Province of Siena / Gaiole in Chianti

            2 6 2 nights min

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

            from £81 / night

            £573 / week

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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

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              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 7 nights min

                • 2 bedrooms
                • sleeps 5
                • 7 nights min
                • Nearest beach 110 km
                • Swimming pool
                • Child friendly

                from £149 / night

                £1,138 - £2,375 / week

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                Responds fast!
                avg. 3 hours 56 minutes

                from £149 / night

                  21

                  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 107 km
                  • Swimming pool
                  • Child friendly

                  from £49 / night

                  £337 - £368 / week

                  Enquire View

                  from £49 / night

                  (1) Excellent 

                    4

                    Holiday b&b in Gaiole in Chianti

                    Province of Siena / Gaiole in Chianti

                    1 2 1 night min

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

                    from £87 / night

                    £594 / week

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                    from £87 / 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 £516 / night

                      £2,623 - £5,551 / week

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                      Responds fast!
                      avg. 3 hours 56 minutes

                      from £516 / night

                        6

                        Gaiole in Chianti holiday farmhouse rental

                        Province of Siena / Gaiole in Chianti

                        2 2 3 nights min

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

                        from £85 / night

                        £564 / week

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                        from £85 / night

                          44

                          Holiday home with shared pool in Gaiole in Chianti

                          Province of Siena / Gaiole in Chianti

                          3 7 7 nights min

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

                          from £111 / night

                          £771 / week

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                          from £111 / night

                            29

                            Gaiole in Chianti holiday home rental

                            Province of Siena / Gaiole in Chianti

                            1 2 7 nights min

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

                            from £77 / night

                            £535 / week

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                            from £77 / 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 £50 / night

                              £345 - £794 / week

                              Enquire View

                              from £50 / night

                              (1) Excellent 

                                22

                                Holiday farmhouse in Montegrossi

                                Gaiole in Chianti / Montegrossi

                                5 10 5 nights min

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

                                from £149 / night

                                £3,958 / week

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                                from £149 / 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

                                  (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 £80 / night

                                    £465 - £693 / week

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                                    Responds fast!
                                    avg. 1 hour 51 minutes

                                    from £80 / 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 £89 / night

                                      £446 - £990 / week

                                      Book View

                                      Responds fast!
                                      avg. 37 minutes

                                      from £89 / 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 £55 / night

                                        £357 / week

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                                        from £55 / 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 £38 / night

                                          £264 - £639 / week

                                          Enquire View

                                          from £38 / night

                                            29

                                            Gaiole in Chianti holiday apartment rental

                                            Province of Siena / Gaiole in Chianti

                                            4 8 3 nights min

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

                                            from £178 / night

                                            £1,117 - £1,355 / week

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                                            Responds fast!
                                            avg. 1 hour 51 minutes

                                            from £178 / night

                                              21

                                              Holiday apartment with shared pool in Gaiole in Chianti

                                              Province of Siena / Gaiole in Chianti

                                              2 5 3 nights min

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

                                              from £104 / night

                                              £614 - £881 / week

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                                              Responds fast!
                                              avg. 1 hour 51 minutes

                                              from £104 / night

                                                17

                                                Nusenna holiday apartment rental

                                                Gaiole in Chianti / Nusenna

                                                2 5 min stay varies

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

                                                from £79 / night

                                                £554 / week

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                                                from £79 / night

                                                  12

                                                  Nusenna holiday home rental

                                                  Gaiole in Chianti / Nusenna

                                                  1 2 1 night min

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

                                                  from £85 / night

                                                  £589 / week

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                                                  from £85 / night

                                                    21

                                                    Holiday guest house in Montefienali

                                                    Gaiole in Chianti / Montefienali

                                                    2 6 min stay varies

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

                                                    from £54 / night

                                                    £347 / week

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                                                    Responds fast!
                                                    avg. 1 hour 19 minutes

                                                    from £54 / 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 £51 / night

                                                      £355 - £770 / week

                                                      Enquire View

                                                      from £51 / night

                                                        22

                                                        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 £41 / night

                                                        £281 - £856 / week

                                                        Enquire View

                                                        from £41 / night

                                                        (41) Excellent 

                                                          24

                                                          Gaiole in Chianti holiday apartment accommodation

                                                          Province of Siena / Gaiole in Chianti

                                                          1 2 4 nights min

                                                          • 1 bedroom
                                                          • sleeps 2
                                                          • 4 nights min
                                                          • 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 11 minutes

                                                          from £103 / 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 £89 / night

                                                            £545 - £772 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 1 hour 51 minutes

                                                            from £89 / 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 £38 / night

                                                              £264 - £627 / week

                                                              Enquire View

                                                              from £38 / 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 £84 / night

                                                                £584 / week

                                                                Book View

                                                                from £84 / night

                                                                  16

                                                                  Holiday b&b rental

                                                                  Gaiole in Chianti / Lecchi

                                                                  1 2 1 night min

                                                                  • 1 bedroom
                                                                  • sleeps 2
                                                                  • 1 night min
                                                                  • Nearest beach 95 km
                                                                  • Swimming pool
                                                                  • Car not necessary

                                                                  from £109 / night

                                                                  £594 / week

                                                                  Book View

                                                                  from £109 / night

                                                                    23

                                                                    Holiday apartment with shared pool in Gaiole in Chianti

                                                                    Province of Siena / Gaiole in Chianti

                                                                    2 5 min stay varies

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

                                                                    from £104 / night

                                                                    £614 - £881 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 1 hour 51 minutes

                                                                    from £104 / 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 £51 / night

                                                                      £354 - £769 / week

                                                                      Enquire View

                                                                      from £51 / night

                                                                        13

                                                                        Nusenna holiday apartment rental

                                                                        Gaiole in Chianti / Nusenna

                                                                        2 5 min stay varies

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

                                                                        from £89 / night

                                                                        £623 / week

                                                                        Book View

                                                                        from £89 / 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 £75 / night

                                                                          £475 - £642 / week

                                                                          Book View

                                                                          from £75 / 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 £55 / night

                                                                            £347 - £901 / week

                                                                            Book View

                                                                            from £55 / 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 £467 / night

                                                                              £3,266 / week

                                                                              Book View

                                                                              from £467 / night

                                                                                20

                                                                                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 £51 / night

                                                                                £355 - £770 / week

                                                                                Enquire View

                                                                                from £51 / night

                                                                                  16

                                                                                  Holiday apartment with shared pool in Nusenna

                                                                                  Gaiole in Chianti / Nusenna

                                                                                  2 4 min stay varies

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

                                                                                  from £70 / night

                                                                                  £485 / week

                                                                                  Book View

                                                                                  from £70 / night

                                                                                  Top Destination reviews

                                                                                  LUXURY APARTMENT WITH PRIVATE GARDEN & VIEWS
                                                                                  Peaceful Retreat

                                                                                  We stayed here for 3 weeks and found this location very central to the entire Chianti region. Heaps to do and see, great accommodation, the unit was extremely well appointed and the pool was a "God-send" especially when temperatures exceeded 45 deg C. Mosquitoes made their unwelcome presence known, their numbers may however diminish as the family of frogs in the garden increases over time. Underground parking was great too helping the car to stay cool. We really appreciated the extent of information available in the compendium which included clear instructuctions on how best to get to various places such as Siena and Firenze. We have to also endorse John's favourite restaurant, Ristorante Il Celliere a Castagnoli. Superb doesn't begin to describe our experience there!!! The locals of Gaiole In Chianti made us feel welcome, especially "Papa" at Tutte Birra. Thanks to John and Tracy for your hospitality.see more
                                                                                  Casacorvo Maggiore: *2019 Early Bird Discounts: Exclusive EV Point Included*
                                                                                  Perfect and plaisant location to explore Tuscany

                                                                                  We were 4 people staying in this very nice apartment : comfortable, clean, modern, well equipped. We loved the location. I never heard of Gaiole before, but it was a nice discovery. Quiet village, but big enough to go out for drink, lunch or dinner or buy some food. Very friendly place and very good location to visit the most important cities around : San Gimigniano, Sienna, Arezzo, Firenze. Good recommendations also in the apartment for hikes around Gaiole. Very lovely villages in this area. We had the most enjoyable time, despite the weather which was not perfect. The swimming pool has a good size also. I would love to go back.see more
                                                                                  Casacorvo Minore *2019 Early Bird Discounts*: *Exclusive EV Point Included*
                                                                                  Very comfortable home away from home

                                                                                  Casacorvo Minore is a very comfortable apartment well located in the heart of Chianti. It has great views from its veranda which fostered perfect starts for each day as we had breakfast sitting in the morning sun. A glass or two in the afternoon was also most pleasant. It helped that the weather was great throughout our stay in Gaiole.see more
                                                                                  EARLY BOOKING DISCOUNT: we offer 10% discount if you book by 31 March!
                                                                                  A hidden gem.

                                                                                  We stayed at Villa LisiDor at the end of May with family. We made the trip to Tuscany by train to Florence from the UK and hired a car from there. We arrived during an unseasonably chilly spell and in torrential rain after a very long journey. Stopping at the Co-op in Radda in Chianti to collect supplies it was a relief to arrive at the villa and chill out. We were met by a charming old gent and despite his lack of English and our lack of Italian we were able to get by with sign language to get some wood for the fire. The main room in the villa is like a baronial hall with a huge inglenook fireplace and long banqueting table. The kitchen is well equipped and the bedrooms are simply furnished and comfortable. A favourite room was the small studio that catches the morning sun. It was too chilly for the pool but we enjoyed a few evenings watching the sun setting over the vineyards. There is an outside kitchen area with dining table and pizza oven which in warmer weather we'd definitely have used. The villa is in a very rural setting but just a short drive to Radda or other local towns and villages. We enjoyed after dinner walks along the track through the vineyards. Very quiet and peaceful if you're looking to get away from it all.see more
                                                                                  EARLY BOOKING DISCOUNT: we offer 10% discount if you book by 31 March!
                                                                                  Villa PetrAlexa - excellent leisure facility

                                                                                  This years stay was even better than our stay last year. Despite the fact we arrived late at night due to repeated traffic jams on the motorway because of terrible weather conditions, everything was perfectly prepared. The house was heated up and food and beverage was available (from the region of course). Everything was clean and tidy. We had great fun during hiking and cycling and enjoyed ourselves in one of the best places in Tuscany. We again had a great time and our next stay is already booked.see more
                                                                                  A HOLIDAY IN THE HEART OF CHIANTI
                                                                                  Authentic unspoiled Italian charm!

                                                                                  My family and I stayed at this beautiful property and had a relaxed and wonderful holiday. Gaiole in Chianti is a small village totally unspoilt by tourism and the location of this property is ideal if you hire a car and travel to all the surroundings various attractions. It is a home from home with everything you could possibly want in a holiday home. The pool is big enough for swimming and both Donatella and her husband were warm, friendly and very helpful. I would highly recommend this property as it is also very secure with entry gates into the property. Tuscany is stunning and a joy to explore the area from this location.see more

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