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    • 3 BR
    • Sleeps 6
    Villa #1150760
      • 7 BR
      • 6 BA
      • 1 HF BA
      • Sleeps 16
      Villa #3219134
      4
        • 3 BR
        • 2 BA
        • Sleeps 8
        Multiple rentals Apartment #489852
        4
        Viewed 6 times in the last 48 hours
          • 7 BR
          • 7 BA
          • Sleeps 13
          Villa #3551389
            • 5 BR
            • 5 BA
            • Sleeps 9
            Villa #3920483
            4
              • 7 BR
              • 5 BA
              • Sleeps 13
              Villa #3544343
              4
                • 5 BR
                • 6 BA
                • 1 HF BA
                • Sleeps 10
                Villa #3219135
                4
                  • 6 BR
                  • 5 BA
                  • Sleeps 11
                  Villa #3544342
                  4
                    Exceptional! 5.0/5
                    (44 reviews)
                    avg/night
                    • 2 BR
                    • 2 BA
                    • Sleeps 4
                    Apartment #433025
                    44
                    Viewed 32 times in the last 48 hours
                      Exceptional! 5.0/5
                      (85 reviews)
                      avg/night
                      • 3 BR
                      • 3 BA
                      • Sleeps 6
                      Villa #95620
                      85
                      Viewed 26 times in the last 48 hours
                        Good! 3.8/5
                        (8 reviews)
                        avg/night
                        • 1 BR
                        • 1 BA
                        • Sleeps 3
                        Apartment #490040
                        8
                        Viewed 30 times in the last 48 hours
                          • 2 BR
                          • 1 BA
                          • Sleeps 5
                          Multiple rentals Apartment #83171
                          21
                            • 5 BR
                            • Sleeps 10
                            Villa #1095146
                            1
                              • 6 BR
                              • 11 BA
                              • Sleeps 12
                              Villa #3585214
                              12
                                • 6 BR
                                • 5 BA
                                • 1 HF BA
                                • Sleeps 12
                                Villa #3711863
                                34
                                  Excellent! 4.6/5
                                  (5 reviews)
                                  avg/night
                                  • 6 BR
                                  • 5 BA
                                  • Sleeps 12
                                  Villa #3812503
                                  5
                                  Viewed 5 times in the last 48 hours
                                    Exceptional! 5.0/5
                                    (6 reviews)
                                    avg/night
                                    • 4 BR
                                    • 3 BA
                                    • Sleeps 12
                                    Villa #1150911
                                    6
                                    Viewed 19 times in the last 48 hours
                                      • 7 BR
                                      • 4 BA
                                      • Sleeps 14
                                      Villa #3219048
                                      3
                                        avg/night
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 4
                                        Apartment #1078249
                                        1
                                        Viewed 11 times in the last 48 hours
                                          • 5 BR
                                          • 4 BA
                                          • Sleeps 10
                                          Villa #3219049
                                          3
                                            • 6 BR
                                            • 1 HF BA
                                            • Sleeps 12
                                            Villa #1150767
                                            6
                                              • 5 BR
                                              • 5 BA
                                              • Sleeps 10
                                              Villa #3219040
                                              5
                                                • 6 BR
                                                • Sleeps 12
                                                Villa #1150859
                                                  • 3 BR
                                                  • 5 BA
                                                  • Sleeps 10
                                                  Villa #3586306
                                                  7
                                                    • 3 BR
                                                    • 4 BA
                                                    • Sleeps 10
                                                    Villa #3219017
                                                      • 8 BR
                                                      • 5 BA
                                                      • Sleeps 16
                                                      Villa #874708
                                                      1
                                                        • 6 BR
                                                        • 6 BA
                                                        • 1 HF BA
                                                        • Sleeps 12
                                                        Villa #3920694
                                                        3
                                                          • 6 BR
                                                          • 5 BA
                                                          • Sleeps 12
                                                          Villa #1948040
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            Apartment #1085004
                                                              • 4 BR
                                                              • 3 BA
                                                              • Sleeps 8
                                                              Apartment #1084999
                                                              1
                                                              Viewed 5 times in the last 48 hours
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                Apartment #1073490
                                                                  • 3 BR
                                                                  • 1 HF BA
                                                                  • Sleeps 6
                                                                  Villa #1150720
                                                                  Viewed 7 times in the last 48 hours
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 8
                                                                    Villa #830535
                                                                    2
                                                                    Viewed 11 times in the last 48 hours
                                                                      • 4 BR
                                                                      • 3 BA
                                                                      • Sleeps 8
                                                                      Apartment #1084998
                                                                      Viewed 5 times in the last 48 hours
                                                                        • 15 BR
                                                                        • 15 BA
                                                                        • Sleeps 35
                                                                        Villa #6706860
                                                                          • 7 BR
                                                                          • 7 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 14
                                                                          Villa #874707
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 7
                                                                            Villa #1072730
                                                                              • 8 BR
                                                                              • 9 BA
                                                                              • Sleeps 18
                                                                              Villa #6706862
                                                                              Viewed 14 times in the last 48 hours
                                                                                • 4 BR
                                                                                • 4 BA
                                                                                • Sleeps 8
                                                                                Villa #3551170
                                                                                1
                                                                                  Exceptional! 5.0/5
                                                                                  (9 reviews)
                                                                                  avg/night
                                                                                  • 6 BR
                                                                                  • 4 BA
                                                                                  • Sleeps 12
                                                                                  Villa #524151
                                                                                  9
                                                                                  Viewed 5 times in the last 48 hours
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 6
                                                                                    Apartment #1085544
                                                                                      • 8 BR
                                                                                      • 11 BA
                                                                                      • Sleeps 16
                                                                                      Villa #3585215
                                                                                      12
                                                                                        • 6 BR
                                                                                        • 8 BA
                                                                                        • Sleeps 14
                                                                                        Villa #6706859
                                                                                          • 3 BR
                                                                                          • Sleeps 8
                                                                                          Villa #1150792
                                                                                          3
                                                                                            • 6 BR
                                                                                            • 6 BA
                                                                                            • Sleeps 12
                                                                                            Villa #3551068
                                                                                            3
                                                                                              • 8 BR
                                                                                              • 1 HF BA
                                                                                              • Sleeps 16
                                                                                              Villa #1150740
                                                                                                • 4 BR
                                                                                                • 5 BA
                                                                                                • Sleeps 8
                                                                                                Villa #3551189
                                                                                                3
                                                                                                  • 16 BR
                                                                                                  • 22 BA
                                                                                                  • Sleeps 31
                                                                                                  Villa #3551062
                                                                                                  3
                                                                                                  Viewed 5 times in the last 48 hours
                                                                                                    • 13 BR
                                                                                                    • 22 BA
                                                                                                    • Sleeps 25
                                                                                                    Villa #3551061
                                                                                                    3
                                                                                                      • 5 BR
                                                                                                      • 8 BA
                                                                                                      • Sleeps 14
                                                                                                      Villa #3551055
                                                                                                      1
                                                                                                      • 1 - 50 of 69

                                                                                                      Gaiole in Chianti: Luxury Vacation Rentals (69)

                                                                                                       

                                                                                                      Recent Gaiole in Chianti Reviews

                                                                                                      Perfect Tuscany countryside experience

                                                                                                      5 of 5
                                                                                                      Staying at Archipettoli was a perfect Tuscany "dream come true" experience. The hospitality of owners Valerio and Gianpaolo was amazing, they live in separate house on the estate and were always helpful when we needed some assistance - like when we locked ourselves out of the house for couple of times during one evening:) Villa itself is decorated in authentic Tuscan country style, with enough space and privacy for several families, with separate beds for up to 12 persons. We enjoyed long dinners in large kitchen downstairs, while the kids could play and watch movies in the tower living rooms. Volterrani family are producing their own amazing wine from Sangiovese grapes grown in surrounding Archipettoli vineyards, and olive oil from their own olive trees. They were kind enough to arrange a shipment of couple of grates of 2011 vintage to us back home to Estonia! Despite late October, it was nice to dive into the refreshing pool after jogging along nearby sloping cypress-lined roads with extraordinary views to typical Chianti countryside. The villa is conveniently located near the main Florence-Sienna highway, with 30-minute drive to Florence. Book now before everyone else discovers this well kept secret!
                                                                                                      • Submitted: Dec 21, 2016
                                                                                                      • Stayed: Oct 2016

                                                                                                      You Will Love Villa Il Santo!

                                                                                                      5 of 5
                                                                                                      Our group of 9 adults and 2 kids stayed at this beautiful villa for a week in June and every single person in our group loved everything about this villa. We started planning the trip nearly a year in advance, and Annagloria was a huge help. She responded quickly to every email and helped us schedule tours, wine tastings, and drivers for the week. When we arrived, we could not believe how beautiful and spacious the villa and grounds were. As gorgeous as the pictures are, they do not do this property justice. The furnishings and décor are truly spectacular and the views over the valley toward San Gimignano from the pool and all the many outdoor seating areas are unbelievable. The villa is also very conveniently located, as we could make easy day trips to the surrounding hill towns and wineries. There are many beautiful properties in Tuscany, but for us what set this one apart were the owners, Annagloria and Enzo. They were friendly and helpful in every way -- from stocking the wine cooler with their own (delicious) wine available for purchase at an incredibly reasonable price, to recommending and making reservations for us at wonderful, small local restaurants, to arranging a magical concert and dinner in an historic nearby church just for their friends and villa renters, to helping us plan a dinner and birthday celebration on the last night with a chef who cooked and served a multi-course dinner for us at the villa. And speaking of chefs, the price for the villa includes a first-night dinner cooked by a wonderful chef, Rosanna. We enjoyed her, and her cooking, so much that we hired her to give us cooking lessons in the villa a few nights later. If you have a chance to do this, we highly recommend it! This week in Tuscany was the highlight of our 3-week trip to Italy, and we cannot wait to come back!
                                                                                                      • Submitted: Nov 29, 2016
                                                                                                      • Stayed: Jun 2016

                                                                                                      Best family vacation we have ever taken!

                                                                                                      4 of 5
                                                                                                      Capanna Cerreto exceeded our every expectation. The villa was immaculately appointed, with jaw dropping views, even more beautiful than the photos lead you to expect. It was perfectly situated to explore Florence, Siena, Montalcino, Montepulciano, Pienza, and San Gimignano as day trips. One of the highlights of our trip was having Chef Graziella prepare dinner for us on the day we arrived. Absolutely the best meal of our trip! Salvatore, the on-site manager, is excellent! He made sure we were comfortable, had everything we needed, and even went to Siena to grab groceries for us because the nearby grocery store in Pianella was closed on the day we arrived! He is an absolute gem of a person!
                                                                                                      • Submitted: Nov 8, 2016
                                                                                                      • Stayed: Aug 2016