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  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
    avg/night
    • 2 BR
    • 2 BA
    • Sleeps 4
    House #2343150
    4
    Viewed 15 times in the last 48 hours
      Exceptional! 5.0/5
      (51 reviews)
      avg/night
      • 2 BR
      • 2 BA
      • Sleeps 4
      House #6235319
      51
      Viewed 48 times in the last 48 hours
        Very Good! 4.0/5
        (5 reviews)
        avg/night
        • 8 BR
        • 4 BA
        • Sleeps 16
        Villa #1934854
        5
        Viewed 25 times in the last 48 hours
          Exceptional! 5.0/5
          (24 reviews)
          avg/night
          • 2 BR
          • 1 BA
          • Sleeps 5
          House #2196590
          24
          Viewed 26 times in the last 48 hours
            • 4 BR
            • 2 BA
            • Sleeps 7
            Multiple rentals Villa #8120549
            Viewed 12 times in the last 48 hours
              Exceptional! 5.0/5
              (10 reviews)
              avg/night
              • 6 BR
              • 6 BA
              • 1 HF BA
              • Sleeps 13
              Villa #3808832
              10
              Viewed 5 times in the last 48 hours
                • 5 BR
                • 5 BA
                • Sleeps 13
                Villa #604892vb
                Viewed 12 times in the last 48 hours
                  Exceptional! 5.0/5
                  (48 reviews)
                  avg/night
                  • 3 BR
                  • 3 BA
                  • Sleeps 6
                  Multiple rentals Villa #64960
                  48
                  Viewed 19 times in the last 48 hours
                    • 2 BR
                    • 1 BA
                    • Sleeps 4
                    Apartment #6852247
                      • 1 BR
                      • 1 BA
                      • Sleeps 4
                      Villa #654136vb
                      4
                      Viewed 7 times in the last 48 hours
                        Wonderful! 4.8/5
                        (19 reviews)
                        avg/night
                        • 2 BR
                        • 1 BA
                        • Sleeps 4
                        Multiple rentals Villa #64960
                        19
                        Viewed 5 times in the last 48 hours
                          • 2 BR
                          • 1 HF BA
                          • Sleeps 4
                          Cottage #1301990
                          3
                          Viewed 8 times in the last 48 hours
                            • 1 BR
                            • 1 BA
                            • Sleeps 4
                            Apartment #2425199
                            Viewed 5 times in the last 48 hours
                              Exceptional! 5.0/5
                              (43 reviews)
                              avg/night
                              • 2 BR
                              • 2 BA
                              • Sleeps 4
                              House #282678vb
                              43
                              Viewed 9 times in the last 48 hours
                                Exceptional! 5.0/5
                                (72 reviews)
                                $71
                                avg/night
                                • 2 BR
                                • 2 BA
                                • 1 HF BA
                                • Sleeps 5
                                Multiple rentals Cottage #6029171
                                72
                                Viewed 75 times in the last 48 hours
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 2
                                  Multiple rentals Chalet #6305435
                                  3
                                    Very Good! 4.0/5
                                    (5 reviews)
                                    $83
                                    avg/night
                                    • 2 BR
                                    • 2 BA
                                    • Sleeps 4
                                    Cottage #696005vb
                                    5
                                    Viewed 15 times in the last 48 hours
                                      Exceptional! 5.0/5
                                      (12 reviews)
                                      avg/night
                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 8
                                      Multiple rentals Farmhouse #1140076
                                      12
                                      Viewed 15 times in the last 48 hours
                                        • 4 BR
                                        • 3 BA
                                        • Sleeps 10
                                        Villa #45144vb
                                        12
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 3
                                          Multiple rentals Chateau / Country House #454623
                                          1
                                            Exceptional! 5.0/5
                                            (60 reviews)
                                            $59
                                            avg/night
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 4
                                            Multiple rentals Apartment #6029171
                                            60
                                            Viewed 62 times in the last 48 hours
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 3
                                              Multiple rentals Apartment #1206876
                                                • 2 BR
                                                • 1 BA
                                                • Sleeps 4
                                                Multiple rentals Apartment #1206876
                                                Viewed 5 times in the last 48 hours
                                                  • 2 BR
                                                  • 1 BA
                                                  • Sleeps 4
                                                  Apartment #6561871
                                                    avg/night
                                                    • 6 BR
                                                    • 4 BA
                                                    • Sleeps 12
                                                    Villa #8159492
                                                    1
                                                    Viewed 11 times in the last 48 hours
                                                      Exceptional! 5.0/5
                                                      (14 reviews)
                                                      avg/night
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 4
                                                      Farmhouse #654067vb
                                                      14
                                                      Viewed 10 times in the last 48 hours
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        Multiple rentals Apartment #38930
                                                        3
                                                          • 2 BR
                                                          • 1 BA
                                                          • 1 HF BA
                                                          • Sleeps 6
                                                          Multiple rentals House #38930
                                                          4
                                                          Viewed 12 times in the last 48 hours
                                                            • 9 BR
                                                            • 5 BA
                                                            • Sleeps 18
                                                            Multiple rentals Villa #1140076
                                                            16
                                                            Viewed 21 times in the last 48 hours
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              Multiple rentals Farmhouse #1140076
                                                              8
                                                                Wonderful! 4.9/5
                                                                (8 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 5
                                                                Multiple rentals Farmhouse #1140076
                                                                8
                                                                Viewed 7 times in the last 48 hours
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 6
                                                                  Multiple rentals Farmhouse #6638853
                                                                    • 7 BR
                                                                    • 4 BA
                                                                    • Sleeps 14
                                                                    Multiple rentals Farmhouse #1140076
                                                                    12
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • Sleeps 7
                                                                      Multiple rentals Farmhouse #6638853
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 6
                                                                        Multiple rentals Farmhouse #6638853
                                                                          • 7 BR
                                                                          • 6 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 16
                                                                          Villa #3219134
                                                                          4
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 2
                                                                            Multiple rentals Villa #6721451
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Sleeps 2
                                                                              Multiple rentals Villa #6721451
                                                                                • 2 BR
                                                                                • 2 BA
                                                                                • Sleeps 4
                                                                                Multiple rentals Villa #6721451
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 3
                                                                                  Multiple rentals Villa #6721451
                                                                                    • 1 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 3
                                                                                    Multiple rentals Villa #6721451
                                                                                      • 3 BR
                                                                                      • Sleeps 6
                                                                                      Villa #1150760
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 5
                                                                                        Multiple rentals Villa #79371
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          Multiple rentals Villa #79371
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 3
                                                                                            Multiple rentals Apartment #79371
                                                                                            1
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              Multiple rentals Villa #79371
                                                                                              2
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 3
                                                                                                Multiple rentals Villa #79371
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  Apartment #1811274
                                                                                                    • 3 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 8
                                                                                                    Villa #829953
                                                                                                    7
                                                                                                    • 1 - 50 of 300+

                                                                                                    Gaiole in Chianti: Apartments, Villas & More (300+)

                                                                                                     

                                                                                                    Recent Gaiole in Chianti Reviews

                                                                                                    A quiet, beautiful property in a remote part of Chianti region. Perfect for a peaceful retreat

                                                                                                    5 of 5
                                                                                                    Very friendly and helpful owners. Clean and well maintained property. Recommend going during harvest and olive oil making season in Oct. I helped harvest olives by hand and found new respect for the process and the difference between hand made olive oil vs. machine made. The only mill in the area with stone wheels, to "gently" crush olives, quite a process. Closest amenities are 3 miles away on a sometimes rough road. Must have a car. Enjoyed staying at the cottage and driving and exploring all the little villages, hamlets and cities in the area.I feel like I have made friends for life, with the property owners! Thank you Francesca and Mateo
                                                                                                    • Submitted: Nov 25, 2016
                                                                                                    • Stayed: Oct 2016

                                                                                                    Stunning views and amazing hosts, a truly Tuscan

                                                                                                    5 of 5
                                                                                                    A group of 17 of us rented out the entire place for 8 days. We had the best time exploring Chianti and Tuscany from Alberto and Camilla's wonderful villa! Between the all the space in the main house and the Hunting lodge, we never felt like we didn't have enough space. Both patios provided plenty of space to sit and amazing views. There are plenty of bathrooms for a large group and plenty of space to sit down for dinners and meals. The kitchens are fully stocked with what you need to cook, but come prepared with groceries unless you have a car. The closest town is a good 20 minute walk and there is hardly anything in there. If you rent a driver and bus, please note that getting down to the house is bumpy and steep, but possible. Do all of your shopping when you are visiting other towns and be prepared to cook dinners or have them cook dinners, the are no restaurants within in short walking distance. I would highly recommend the pizza by Alberto and any dinners by both of them. Everything they made was pure Tuscan heaven and memorable. Come hungry, they out due themselves. I would also recommend dinner at Dievole, a winery very close to them for one evening. Alberto and Camilla will make you feel so welcome and will make this trip a once in a lifetime experience. Camilla is a terrific guide and I would highly recommend booking her for a full day visit to Siena (a magical city). She also took us to Pienza and Montalcino, she is very knowledgeable and will provide an amazing guided tour. I highly recommend this location and house! The house itself is very comfortable, but slightly rustic. If you are looking for something modern or new, you will not find it here. The beds are comfortable, rooms are clean, and the space is great. I hope you can visit this part of Chianti/Tuscany!
                                                                                                    • Submitted: Oct 24, 2016
                                                                                                    • Stayed: Oct 2016

                                                                                                    Stunning views and amazing hosts, a truly Tuscan f

                                                                                                    5 of 5
                                                                                                    A group of 17 of us rented out the entire place for 8 days. We had the best time exploring Chianti and Tuscany from Alberto and Camilla's wonderful villa! Between the all the space in the main house and the Hunting lodge, we never felt like we didn't have enough space. Both patios provided plenty of space to sit and amazing views. There are plenty of bathrooms for a large group and plenty of space to sit down for dinners and meals. The kitchens are fully stocked with what you need to cook, but come prepared with groceries unless you have a car. The closest town is a good 20 minute walk and there is hardly anything in there. If you rent a driver and bus, please note that getting down to the house is bumpy and steep, but possible. Do all of your shopping when you are visiting other towns and be prepared to cook dinners or have them cook dinners, the are no restaurants within in short walking distance. I would highly recommend the pizza by Alberto and any dinners by both of them. Everything they made was pure Tuscan heaven and memorable. Come hungry, they out due themselves. I would also recommend dinner at Dievole, a winery very close to them for one evening. Alberto and Camilla will make you feel so welcome and will make this trip a once in a lifetime experience. Camilla is a terrific guide and I would highly recommend booking her for a full day visit to Siena (a magical city). She also took us to Pienza and Montalcino, she is very knowledgeable and will provide an amazing guided tour. I highly recommend this location and house! The house itself is very comfortable, but slightly rustic. If you are looking for something modern or new, you will not find it here. The beds are comfortable, rooms are clean, and the space is great. I hope you can visit this part of Chianti/Tuscany!
                                                                                                    • Submitted: Oct 24, 2016
                                                                                                    • Stayed: Oct 2016