check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!
  • 1 - 50 of 149
Additional fees apply. Taxes may be added.
    • 3 BR
    • 3 BA
    • Sleeps 6
    46
      • 2 BR
      • 1 BA
      • Sleeps 4
      18
        • 7 BR
        • 6 BA
        • 1 HF BA
        • Sleeps 16
        4
          • 1 BR
          • 1 BA
          • Sleeps 2
            • 1 BR
            • 1 BA
            • Sleeps 2
              • 2 BR
              • 2 BA
              • Sleeps 4
                • 1 BR
                • 1 BA
                • Sleeps 3
                  • 2 BR
                  • 2 BA
                  • Sleeps 5
                    • 2 BR
                    • 1 BA
                    • Sleeps 4
                      • 1 BR
                      • 1 BA
                      • Sleeps 3
                        • 1 BR
                        • 1 BA
                        • Sleeps 3
                          • 2 BR
                          • 1 BA
                          • Sleeps 4
                          1 Review
                            • 1 BR
                            • 1 BA
                            • Sleeps 4
                            3
                              • 5 BR
                              • 6 BA
                              • Sleeps 12
                              28
                                • 4 BR
                                • 3 BA
                                • Sleeps 10
                                11
                                  • 3 BR
                                  • 3 BA
                                  • Sleeps 8
                                  6
                                    • 6 BR
                                    • 4 BA
                                    • Sleeps 12
                                    1 Review
                                      • 6 BR
                                      • 5 BA
                                      • Sleeps 12
                                      7
                                        • 5 BR
                                        • 4 BA
                                        • Sleeps 11
                                        5
                                          • 5 BR
                                          • 5 BA
                                          • Sleeps 11
                                            • 4 BR
                                            • 3 BA
                                            • Sleeps 10
                                            2 Reviews
                                              • 5 BR
                                              • 3 BA
                                              • Sleeps 10
                                              4
                                                • 5 BR
                                                • 5 BA
                                                • Sleeps 13
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 4
                                                  1 Review
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 5
                                                    3
                                                      • 3 BR
                                                      • 3 BA
                                                      • Sleeps 8
                                                        • 6 BR
                                                        • 1 BA
                                                        • Sleeps 12
                                                          • 5 BR
                                                          • 6 BA
                                                          • Sleeps 10
                                                            • 5 BR
                                                            • 6 BA
                                                            • Sleeps 10
                                                              • 5 BR
                                                              • 5 BA
                                                              • Sleeps 10
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                  • 6 BR
                                                                  • 4 BA
                                                                  • Sleeps 14
                                                                  2 Reviews
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    1 Review
                                                                      • 4 BR
                                                                      • 4 BA
                                                                      • Sleeps 8
                                                                        • 3 BR
                                                                        • 3 BA
                                                                        • Sleeps 8
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 2
                                                                            1 Review
                                                                              • 4 BR
                                                                              • 4 BA
                                                                              • Sleeps 8
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 6
                                                                                1 Review
                                                                                  • 2 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                    • 4 BR
                                                                                    • 4 BA
                                                                                    • Sleeps 8
                                                                                    2 Reviews
                                                                                      • 7 BR
                                                                                      • 7 BA
                                                                                      • Sleeps 14
                                                                                        • 4 BR
                                                                                        • 4 BA
                                                                                        • Sleeps 8
                                                                                          • 4 BR
                                                                                          • 4 BA
                                                                                          • Sleeps 8
                                                                                          • 1 - 50 of 149
                                                                                           

                                                                                          Recent Gaiole in Chianti Reviews

                                                                                          Absolutely wonderful visit!

                                                                                          5 of 5
                                                                                          What a stunningly beautiful place! Us and friends (12 altogether) stayed here for a week in July 2016. I selected this place without input from my friends and so was really pleased when my friends were astounded by how beautiful it was. The house had so much space (much bigger than it looks in the photos), very comfortable bedrooms and so many great social family areas to relax in. It had the perfect farmhouse kitchen for a large group! We had other friends for dinner one night and comfortably cooked in the lovely kitchen and ate outdoors - all 22 of us! The outdoor area is gorgeous, pool immaculate and views superb. You have both of best worlds here as although we visited in the busy tourist season and were only a few minutes walk from Gaiole in Chianti, the location and house was so quiet and peaceful there. We had excellent communication with the owner and great local support for any questions we had while we were there. The only regret was that we did not stay longer! We all agreed we should have stayed for at least 2 weeks minimum! Thanks so much for letting us stay in this lovely family home!!
                                                                                          • Submitted: Jul 22, 2016
                                                                                          • Stayed: Jul 2016

                                                                                          It was a great experience Luxury Retreats surpassed my expectations.

                                                                                          5 of 5
                                                                                          I stayed at two houses in Tuscany, everything was great, houses were amazing, service and just feeling the concierges were taking care of us. Maccinaia in particular had the live in concierge and they couple is just amazing. The house was wonderful except that I might have chosen a house closer to a town. Maccinaia is very well set in the mountains and the views are spectacular and the roads to get to it are very curvy and many of them are no paved so you need a car that can drive well thru the different roads. Other than that it surpassed my expectations.
                                                                                          • Submitted: Jul 9, 2016
                                                                                          • Stayed: Jul 2016

                                                                                          The Wine is Fine in Gaiole

                                                                                          5 of 5
                                                                                          This property is truly amazing....photos cannot adequately capture its overall charm and natural beauty! This luxury villa offers views of the spectacular sprawling vineyards from almost every window. And if you are in the mood for some of the best Chianti the area has to offer ....don't miss this!!! Wine maker Paula Cook has perfected this wine, and after many wine tastings in the region...Le Miccine is the winner hands down. The villa is also close to Siene, Florence and other small Tuscan villages with great cafes and dining experiences. Our hosts owner Jimmy and others Carmen and Sabrina, Isabella and Chloe treated us like royalty and went above and beyond to make our stay a pleasure. We also enjoyed a sumptuous private dinner prepared by Lorenzo Migliorini prepared fresh in our villa kitchen. We enjoyed it all so much we hired him the next day for private escorted wine tour of some of the most scenic and tasteful vineyards in the Chianti region. This memorable day was a trip highlight and a perfect way to spend our 30 year wedding anniversary and included lunch outdoors on a vineyard hosted by a lovely Italian family. Would highly recommend Lorenzo...he was amazing!!! We thoroughly enjoyed this experience and this property includes everything needed to create a fabulous Tuscan experience. Our dear friends and travel companions included a chef who cooked for us as well. The kitchen contains everything needed to make the best cuisine with nearby stores with fresh produce, cheeses, breads and meats to create our own feast. I would highly recommend this property and of course the wine!!! Cheers to Paula and her dad Jimmy on a job well done!!!
                                                                                          • Submitted: Jun 13, 2016
                                                                                          • Stayed: May 2016