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In a peaceful rural location amidst the famous Chianti vineyards of Tuscany, holiday rental accommodation in Gaiole in Chianti couldn't be much better situated for anyone hoping to experience a fascinating cultural heritage of which wine production plays such an important part, particularly in the province of Siena - holiday villas and apartments in Gaiole in Chianti proving to be a popular choice for wine-buffs and gastronomes seeking the perfect place in which to indulge their passion for a cuisine that is unmistakeably Italian. Holiday accommodation in Gaiole in Chianti has so much more to offer the visitor than superb eating and drinking, although anyone who loves food would agree that the ideal way to end any day of your vacation is by relaxing and enjoying a meal made using the local produce of Tuscany - holiday apartments and villas in Gaiole in Chianti being found surrounded by miles of spectacular landscapes that simply beg to be explored on foot, horse-back or by mountain-bike, so after a day of energetic outdoor activities in the sun-drenched fresh air of the Tuscan countryside, you'll be ready to race back to your holiday rental accommodation in Gaiole in Chianti to prepare a well-deserved feast or sample the culinary delights offered by any one of a fabulous selection of restaurants in the area.

Additional service fee may apply.
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    Exceptional! 5/5
    (4 reviews)
    avg/night
    Villa #8155527
    • 5 BR
    • 4 BA
    • Sleeps 10
    4
    Viewed 11 times in the last 48 hours

    Confirmation within 24 hours

    Your booking request will be confirmed or denied within 24 hours.

      Exceptional! 5/5
      (50 reviews)
      avg/night
      Multiple rentals Villa #64960
      • 3 BR
      • 3 BA
      • Sleeps 6
      50
      Viewed 33 times in the last 48 hours

      Instant confirmation

      Your booking request will be confirmed immediately.

        Wonderful! 4.8/5
        (19 reviews)
        avg/night
        Multiple rentals Villa #64960
        • 2 BR
        • 1 BA
        • Sleeps 4
        19
        Viewed 18 times in the last 48 hours

        Instant confirmation

        Your booking request will be confirmed immediately.

          Wonderful! 4.9/5
          (8 reviews)
          avg/night
          Multiple rentals Apartment #489852
          • 1 BR
          • 1 BA
          • Sleeps 4
          8
          Viewed 6 times in the last 48 hours

          Confirmation within 24 hours

          Your booking request will be confirmed or denied within 24 hours.

            Chateau / Country House #2031854
            • 1 BR
            • Sleeps 3
            7

            Confirmation within 24 hours

            Your booking request will be confirmed or denied within 24 hours.

              Multiple rentals Villa #76109
              • 6 BR
              • 5 BA
              • Sleeps 12
              8
              Viewed 12 times in the last 48 hours

              Confirmation within 24 hours

              Your booking request will be confirmed or denied within 24 hours.

                Multiple rentals Apartment #1206876
                • 2 BR
                • 1 BA
                • Sleeps 4
                Viewed 8 times in the last 48 hours

                Confirmation within 24 hours

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                  Villa #281961vb
                  • 5 BR
                  • 6 BA
                  • Sleeps 12
                  29

                  Confirmation within 24 hours

                  Your booking request will be confirmed or denied within 24 hours.

                    Villa #45144vb
                    • 4 BR
                    • 3 BA
                    • Sleeps 10
                    12

                    Confirmation within 24 hours

                    Your booking request will be confirmed or denied within 24 hours.

                      Villa #8043542
                      • 3 BR
                      • 3 BA
                      • Separate Toilet
                      • Sleeps 7
                      2

                      Instant confirmation

                      Your booking request will be confirmed immediately.

                        avg/night
                        Villa #8159492
                        • 6 BR
                        • 4 BA
                        • Sleeps 12
                        1
                        Viewed 14 times in the last 48 hours

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                        Your booking request will be confirmed or denied within 24 hours.

                          Multiple rentals Apartment #1206876
                          • 1 BR
                          • 1 BA
                          • Sleeps 3

                          Confirmation within 24 hours

                          Your booking request will be confirmed or denied within 24 hours.

                            Exceptional! 5/5
                            (39 reviews)
                            avg/night
                            Farmhouse #262966vb
                            • 2 BR
                            • 2 BA
                            • Sleeps 4
                            39
                            Viewed 5 times in the last 48 hours

                            Confirmation within 24 hours

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                              Villa #604892vb
                              • 5 BR
                              • 5 BA
                              • Sleeps 13
                              Viewed 7 times in the last 48 hours

                              Confirmation within 24 hours

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                                Villa #8042755
                                • 4 BR
                                • 3 BA
                                • Sleeps 10
                                2
                                Viewed 13 times in the last 48 hours

                                Instant confirmation

                                Your booking request will be confirmed immediately.

                                  Multiple rentals Apartment #1206876
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 6
                                  3
                                  Viewed 15 times in the last 48 hours

                                  Confirmation within 24 hours

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                                    avg/night
                                    Multiple rentals Villa #6721451
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 3
                                    Viewed 6 times in the last 48 hours

                                    Confirmation within 24 hours

                                    Your booking request will be confirmed or denied within 24 hours.

                                      Excellent! 4.7/5
                                      (6 reviews)
                                      avg/night
                                      Multiple rentals Villa #76109
                                      • 5 BR
                                      • 4 BA
                                      • Sleeps 11
                                      6
                                      Viewed 8 times in the last 48 hours

                                      Confirmation within 24 hours

                                      Your booking request will be confirmed or denied within 24 hours.

                                        Exceptional! 5/5
                                        (4 reviews)
                                        avg/night
                                        Multiple rentals Apartment #489852
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 8
                                        4
                                        Viewed 7 times in the last 48 hours

                                        Confirmation within 24 hours

                                        Your booking request will be confirmed or denied within 24 hours.

                                          Multiple rentals Villa #1050128
                                          • 3 BR
                                          • 3 BA
                                          • Sleeps 6
                                          Viewed 8 times in the last 48 hours

                                          Confirmation within 24 hours

                                          Your booking request will be confirmed or denied within 24 hours.

                                            Apartment #1889156
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 6
                                            1

                                            Confirmation within 24 hours

                                            Your booking request will be confirmed or denied within 24 hours.

                                              Multiple rentals Apartment #1206876
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 3
                                              2

                                              Confirmation within 24 hours

                                              Your booking request will be confirmed or denied within 24 hours.

                                                Excellent! 4.7/5
                                                (3 reviews)
                                                avg/night
                                                Multiple rentals House #76109
                                                • Studio
                                                • 1 BA
                                                • Sleeps 2
                                                3
                                                Viewed 17 times in the last 48 hours

                                                Confirmation within 24 hours

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                                                  avg/night
                                                  Multiple rentals Villa #6721451
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 2
                                                  Viewed 7 times in the last 48 hours

                                                  Confirmation within 24 hours

                                                  Your booking request will be confirmed or denied within 24 hours.

                                                    Multiple rentals Villa #6721451
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 2

                                                    Confirmation within 24 hours

                                                    Your booking request will be confirmed or denied within 24 hours.

                                                      avg/night
                                                      Multiple rentals Villa #6721451
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 4
                                                      Viewed 8 times in the last 48 hours

                                                      Confirmation within 24 hours

                                                      Your booking request will be confirmed or denied within 24 hours.

                                                        Multiple rentals Villa #6721451
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 3

                                                        Confirmation within 24 hours

                                                        Your booking request will be confirmed or denied within 24 hours.

                                                          Wonderful! 4.8/5
                                                          (4 reviews)
                                                          avg/night
                                                          Multiple rentals House #1329957a
                                                          • 3 BR
                                                          • 3 BA
                                                          • Sleeps 6
                                                          4
                                                          Viewed 16 times in the last 48 hours

                                                          Confirmation within 24 hours

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                                                            Multiple rentals Farmhouse #1329957a
                                                            • 6 BR
                                                            • 6 BA
                                                            • Sleeps 12
                                                            Viewed 7 times in the last 48 hours

                                                            Confirmation within 24 hours

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                                                              Multiple rentals Villa #1050128
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 2

                                                              Confirmation within 24 hours

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                                                                Multiple rentals Villa #1050128
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 4
                                                                1

                                                                Confirmation within 24 hours

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                                                                  Apartment #8068069
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 4
                                                                  1

                                                                  Confirmation within 24 hours

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                                                                    House #3517315
                                                                    • 5 BR
                                                                    • 5 BA
                                                                    • Sleeps 10
                                                                    3

                                                                    Confirmation within 24 hours

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                                                                      House #6957959
                                                                      • 5 BR
                                                                      • 4 BA
                                                                      • Sleeps 10

                                                                      Confirmation within 24 hours

                                                                      Your booking request will be confirmed or denied within 24 hours.

                                                                        Villa #8070602
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 6
                                                                        3
                                                                        Viewed 7 times in the last 48 hours

                                                                        Confirmation within 24 hours

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                                                                          Apartment #6785309
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 4

                                                                          Confirmation within 24 hours

                                                                          Your booking request will be confirmed or denied within 24 hours.

                                                                            Apartment #6825046
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Sleeps 4

                                                                            Confirmation within 24 hours

                                                                            Your booking request will be confirmed or denied within 24 hours.

                                                                              Apartment #6825051
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Sleeps 3

                                                                              Confirmation within 24 hours

                                                                              Your booking request will be confirmed or denied within 24 hours.

                                                                                Villa #1150760
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 6

                                                                                Confirmation within 24 hours

                                                                                Your booking request will be confirmed or denied within 24 hours.

                                                                                  Apartment #6785310
                                                                                  • 2 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4

                                                                                  Confirmation within 24 hours

                                                                                  Your booking request will be confirmed or denied within 24 hours.

                                                                                    Villa #8052862
                                                                                    • 5 BR
                                                                                    • 5 BA
                                                                                    • Separate Toilet
                                                                                    • Sleeps 13

                                                                                    Confirmation within 24 hours

                                                                                    Your booking request will be confirmed or denied within 24 hours.

                                                                                      Apartment #6785311
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 2

                                                                                      Confirmation within 24 hours

                                                                                      Your booking request will be confirmed or denied within 24 hours.

                                                                                        Apartment #442176vb
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 4
                                                                                        2

                                                                                        Confirmation within 24 hours

                                                                                        Your booking request will be confirmed or denied within 24 hours.

                                                                                          Apartment #2343146
                                                                                          • Studio
                                                                                          • 1 BA
                                                                                          • Sleeps 2

                                                                                          Instant confirmation

                                                                                          Your booking request will be confirmed immediately.

                                                                                            Villa #6872036
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 8

                                                                                            Confirmation within 24 hours

                                                                                            Your booking request will be confirmed or denied within 24 hours.

                                                                                              Multiple rentals Villa #79371
                                                                                              • 2 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 5
                                                                                              Viewed 6 times in the last 48 hours

                                                                                              Confirmation within 24 hours

                                                                                              Your booking request will be confirmed or denied within 24 hours.

                                                                                                Multiple rentals Villa #79371
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 4

                                                                                                Confirmation within 24 hours

                                                                                                Your booking request will be confirmed or denied within 24 hours.

                                                                                                  Multiple rentals Villa #79371
                                                                                                  • 2 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  2
                                                                                                  Viewed 7 times in the last 48 hours

                                                                                                  Confirmation within 24 hours

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                                                                                                    Multiple rentals Apartment #79371
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 3
                                                                                                    1
                                                                                                    Viewed 6 times in the last 48 hours

                                                                                                    Confirmation within 24 hours

                                                                                                    Your booking request will be confirmed or denied within 24 hours.

                                                                                                      Multiple rentals Villa #79371
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 3

                                                                                                      Confirmation within 24 hours

                                                                                                      Your booking request will be confirmed or denied within 24 hours.

                                                                                                      • 1 - 50 of 300+

                                                                                                      Holiday Accommodation Gaiole in Chianti (300+)