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  • Showing 1-50 of 112
Additional fees apply. Taxes may be added.
    avg/night
    • 2 BR
    • 2 BA
    • 1 HF BA
    • Sleeps 6
    Apartment #4077544
    1
    Viewed 7 times in the last 48 hours
      • 3 BR
      • 3 BA
      • Sleeps 8
      Multiple rentals Apartment #434868
      14
        • 6 BR
        • 5 BA
        • 1 HF BA
        • Sleeps 12
        Villa #3711863
        34
          • 1 BR
          • 1 BA
          • Sleeps 3
          Apartment #6777317
          2
            • 2 BR
            • 1 BA
            • Sleeps 5
            Multiple rentals Apartment #83171
            21
              • 1 BR
              • 1 BA
              • 1 HF BA
              • Sleeps 2
              Apartment #831601
              30
                • 1 BR
                • 1 BA
                • Sleeps 4
                Multiple rentals Villa #71745
                20
                  Wonderful! 4.9/5
                  (19 reviews)
                  avg/night
                  • 1 BR
                  • 1 BA
                  • Sleeps 4
                  Apartment #1107906
                  19
                  Viewed 21 times in the last 48 hours
                    • 1 BR
                    • 1 BA
                    • Sleeps 3
                    Apartment #1107364
                    3
                      • 5 BR
                      • Sleeps 10
                      Villa #1095146
                      1
                        • 6 BR
                        • 5 BA
                        • Sleeps 12
                        Villa #3812503
                        5
                          • 2 BR
                          • 2 BA
                          • Sleeps 6
                          Villa #1878886
                            • 4 BR
                            • 5 BA
                            • Sleeps 7
                            Villa #3931004
                            1
                              • 8 BR
                              • 5 BA
                              • Sleeps 16
                              Villa #874708
                              1
                                • 7 BR
                                • 7 BA
                                • Sleeps 13
                                Villa #3551389
                                  • 6 BR
                                  • 5 BA
                                  • Sleeps 12
                                  Villa #1948040
                                    • 6 BR
                                    • 6 BA
                                    • 1 HF BA
                                    • Sleeps 12
                                    Villa #3920694
                                    3
                                      • 7 BR
                                      • 4 BA
                                      • Sleeps 14
                                      Villa #3219048
                                      3
                                        • 15 BR
                                        • 15 BA
                                        • Sleeps 35
                                        Villa #6706860
                                          • 8 BR
                                          • 9 BA
                                          • Sleeps 18
                                          Villa #6706862
                                            • 5 BR
                                            • 4 BA
                                            • Sleeps 10
                                            Villa #3219049
                                            3
                                              Exceptional! 5.0/5
                                              (8 reviews)
                                              avg/night
                                              • 6 BR
                                              • 4 BA
                                              • Sleeps 12
                                              Villa #524151
                                              8
                                              Viewed 7 times in the last 48 hours
                                                • 6 BR
                                                • 8 BA
                                                • Sleeps 14
                                                Villa #6706859
                                                  • 6 BR
                                                  • 5 BA
                                                  • Sleeps 13
                                                  Villa #3544343
                                                  4
                                                    • 6 BR
                                                    • 11 BA
                                                    • Sleeps 12
                                                    Villa #3585214
                                                    12
                                                      • 5 BR
                                                      • 5 BA
                                                      • Sleeps 10
                                                      Villa #3219040
                                                      5
                                                        • 6 BR
                                                        • 5 BA
                                                        • Sleeps 11
                                                        Villa #3544342
                                                        4
                                                          • 5 BR
                                                          • 5 BA
                                                          • Sleeps 9
                                                          Villa #3920483
                                                          4
                                                            • 8 BR
                                                            • 11 BA
                                                            • Sleeps 16
                                                            Villa #3585215
                                                            12
                                                              • 6 BR
                                                              • 6 BA
                                                              • Sleeps 12
                                                              Villa #3551068
                                                              3
                                                                • 3 BR
                                                                • 4 BA
                                                                • Sleeps 10
                                                                Villa #3219017
                                                                  • 3 BR
                                                                  • 5 BA
                                                                  • Sleeps 10
                                                                  Villa #3586306
                                                                  7
                                                                    • 15 BR
                                                                    • 22 BA
                                                                    • Sleeps 31
                                                                    Villa #3551062
                                                                    3
                                                                      • 4 BR
                                                                      • 3 BA
                                                                      • Sleeps 12
                                                                      Villa #1150911
                                                                      3
                                                                        • 12 BR
                                                                        • 22 BA
                                                                        • Sleeps 25
                                                                        Villa #3551061
                                                                        3
                                                                        Viewed 5 times in the last 48 hours
                                                                          • 5 BR
                                                                          • 6 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 10
                                                                          Villa #3219135
                                                                          4
                                                                            • 7 BR
                                                                            • 7 BA
                                                                            • Sleeps 12
                                                                            Villa #3920565
                                                                            31
                                                                              • 5 BR
                                                                              • 8 BA
                                                                              • Sleeps 14
                                                                              Villa #3551055
                                                                              1
                                                                                • 6 BR
                                                                                • 1 HF BA
                                                                                • Sleeps 12
                                                                                Villa #1150767
                                                                                3
                                                                                  • 6 BR
                                                                                  • 8 BA
                                                                                  • Sleeps 16
                                                                                  Villa #3551056
                                                                                  1
                                                                                    • 10 BR
                                                                                    • 10 BA
                                                                                    • Sleeps 20
                                                                                    Villa #3629348
                                                                                      • 5 BR
                                                                                      • 8 BA
                                                                                      • Sleeps 12
                                                                                      Villa #3651217
                                                                                      1
                                                                                        • 5 BR
                                                                                        • 8 BA
                                                                                        • Sleeps 10
                                                                                        Villa #3651216
                                                                                        1
                                                                                          • 17 BR
                                                                                          • 22 BA
                                                                                          • Sleeps 35
                                                                                          Villa #3586422
                                                                                          3
                                                                                            • 3 BR
                                                                                            • 3 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 6
                                                                                            Villa #3551487
                                                                                            1
                                                                                              • 9 BR
                                                                                              • 9 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 18
                                                                                              Villa #3551178
                                                                                                • 6 BR
                                                                                                • 6 BA
                                                                                                • Sleeps 12
                                                                                                Villa #3551118
                                                                                                1
                                                                                                  • 6 BR
                                                                                                  • 7 BA
                                                                                                  • Sleeps 12
                                                                                                  Villa #1150886
                                                                                                  4
                                                                                                  • 1 - 50 of 112

                                                                                                  Castellina in Chianti: Luxury Vacation Rentals (112)

                                                                                                   

                                                                                                  Recent Castellina in Chianti Reviews

                                                                                                  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

                                                                                                  The Best Holiday :)

                                                                                                  5 of 5
                                                                                                  "Poggio Nuccioli" is the perfect base for a holiday in Tuscany, owners are extremely kind and attentive, views were spectacular from the bedrooms and terrace. The property is close to Florence, Lucca, Greve and we appreciated the major venues for art, the important churches and Florentine landmarks.
                                                                                                  • Submitted: Nov 12, 2016
                                                                                                  • Stayed: Jul 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