HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
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 svg-report-flag pet-dog svg-multiunit
  • Showing 1-50 of 300+
Additional service fee may apply.
    • 3 BR
    • 3 BA
    • Sleeps 6
    Villa #6911041
      • 11 BR
      • 4 BA
      • Sleeps 22
      Villa #6487068
        • 2 BR
        • 2 BA
        • Sleeps 4
        Villa #6489703
          Exceptional! 5.0/5
          (13 reviews)
          avg/night
          • 4 BR
          • 3 BA
          • Sleeps 11
          Villa #607748vb
          13
          Viewed 51 times in the last 48 hours
            Wonderful! 4.9/5
            (21 reviews)
            avg/night
            • 3 BR
            • 3 BA
            • Sleeps 6
            Villa #421433
            21
            Viewed 43 times in the last 48 hours
              Exceptional! 5.0/5
              (12 reviews)
              avg/night
              • 4 BR
              • 4 BA
              • Sleeps 9
              Villa #602659vb
              12
              Viewed 114 times in the last 48 hours
                Wonderful! 4.8/5
                (9 reviews)
                avg/night
                • 5 BR
                • 4 BA
                • Separate Toilet
                • Sleeps 9
                Villa #761658vb
                9
                Viewed 48 times in the last 48 hours
                  avg/night
                  • 5 BR
                  • 5 BA
                  • Separate Toilet
                  • Sleeps 10
                  Villa #1097226
                  4
                  Viewed 92 times in the last 48 hours
                    Wonderful! 4.8/5
                    (9 reviews)
                    avg/night
                    • 4 BR
                    • 3 BA
                    • Separate Toilet
                    • Sleeps 6
                    Villa #64607vb
                    9
                    Viewed 30 times in the last 48 hours
                      Wonderful! 4.9/5
                      (18 reviews)
                      avg/night
                      • 5 BR
                      • 4 BA
                      • Sleeps 12
                      Villa #90810
                      18
                      Viewed 73 times in the last 48 hours
                        Exceptional! 5.0/5
                        (17 reviews)
                        avg/night
                        • 4 BR
                        • 4 BA
                        • Separate Toilet
                        • Sleeps 10
                        Multiple rentals Villa #1898892
                        17
                        Viewed 53 times in the last 48 hours
                          Exceptional! 5.0/5
                          (29 reviews)
                          avg/night
                          • 6 BR
                          • 6 BA
                          • Separate Toilet
                          • Sleeps 12
                          Villa #1636667
                          29
                          Viewed 44 times in the last 48 hours
                            Excellent! 4.5/5
                            (6 reviews)
                            avg/night
                            • 3 BR
                            • 2 BA
                            • Sleeps 9
                            Villa #1920987
                            6
                            Viewed 38 times in the last 48 hours
                              Wonderful! 4.9/5
                              (30 reviews)
                              avg/night
                              • 3 BR
                              • 3 BA
                              • Separate Toilet
                              • Sleeps 7
                              Villa #709879vb
                              30
                              Viewed 97 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 34 times in the last 48 hours
                                  Exceptional! 5.0/5
                                  (28 reviews)
                                  avg/night
                                  • 5 BR
                                  • 4 BA
                                  • Sleeps 9
                                  Villa #999599
                                  28
                                  Viewed 43 times in the last 48 hours
                                    Wonderful! 4.9/5
                                    (30 reviews)
                                    avg/night
                                    • 5 BR
                                    • 5 BA
                                    • Sleeps 10
                                    Villa #275267
                                    30
                                    Viewed 40 times in the last 48 hours
                                      avg/night
                                      • 6 BR
                                      • 7 BA
                                      • Separate Toilet
                                      • Sleeps 12
                                      Villa #8052426
                                      2
                                      Viewed 14 times in the last 48 hours
                                        Wonderful! 4.8/5
                                        (6 reviews)
                                        avg/night
                                        • 7 BR
                                        • 6 BA
                                        • Sleeps 16
                                        Villa #1856413
                                        6
                                        Viewed 115 times in the last 48 hours
                                          Excellent! 4.6/5
                                          (14 reviews)
                                          avg/night
                                          • 4 BR
                                          • 3 BA
                                          • Sleeps 8
                                          Villa #8024274
                                          14
                                          Viewed 37 times in the last 48 hours
                                            • 1 BR
                                            • 1 BA
                                            • Sleeps 4
                                            Villa #654136vb
                                            4
                                            Viewed 138 times in the last 48 hours
                                              Exceptional! 5.0/5
                                              (51 reviews)
                                              avg/night
                                              • 5 BR
                                              • 3 BA
                                              • Sleeps 12
                                              Villa #15258
                                              51
                                              Viewed 14 times in the last 48 hours
                                                Wonderful! 4.8/5
                                                (9 reviews)
                                                avg/night
                                                • 5 BR
                                                • 3 BA
                                                • Sleeps 10
                                                Villa #6256561
                                                9
                                                Viewed 44 times in the last 48 hours
                                                  Wonderful! 4.8/5
                                                  (11 reviews)
                                                  avg/night
                                                  • 4 BR
                                                  • 4 BA
                                                  • Sleeps 10
                                                  Villa #6661747
                                                  11
                                                  Viewed 25 times in the last 48 hours
                                                    Excellent! 4.7/5
                                                    (9 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 5
                                                    Villa #1722262
                                                    9
                                                    Viewed 39 times in the last 48 hours
                                                      Excellent! 4.6/5
                                                      (9 reviews)
                                                      avg/night
                                                      • 5 BR
                                                      • 4 BA
                                                      • Sleeps 10
                                                      Villa #663793vb
                                                      9
                                                      Viewed 38 times in the last 48 hours
                                                        • 9 BR
                                                        • 5 BA
                                                        • Separate Toilet
                                                        • Sleeps 18
                                                        Villa #6048097
                                                        Viewed 19 times in the last 48 hours
                                                          • 3 BR
                                                          • 3 BA
                                                          • Sleeps 6
                                                          Villa #6790450
                                                          Viewed 29 times in the last 48 hours
                                                            • 9 BR
                                                            • 8 BA
                                                            • Sleeps 18
                                                            Villa #1934124
                                                            4
                                                            Viewed 96 times in the last 48 hours
                                                              • 5 BR
                                                              • 3 BA
                                                              • Separate Toilet
                                                              • Sleeps 12
                                                              Villa #6546872
                                                              Viewed 111 times in the last 48 hours
                                                                • 5 BR
                                                                • 2 BA
                                                                • Separate Toilet
                                                                • Sleeps 9
                                                                Villa #6790479
                                                                Viewed 10 times in the last 48 hours
                                                                  Exceptional! 5.0/5
                                                                  (7 reviews)
                                                                  avg/night
                                                                  • 4 BR
                                                                  • 4 BA
                                                                  • Sleeps 8
                                                                  Villa #6555585
                                                                  7
                                                                  Viewed 16 times in the last 48 hours
                                                                    Exceptional! 5.0/5
                                                                    (9 reviews)
                                                                    avg/night
                                                                    • 9 BR
                                                                    • 7 BA
                                                                    • Separate Toilet
                                                                    • Sleeps 18
                                                                    Villa #620449vb
                                                                    9
                                                                    Viewed 39 times in the last 48 hours
                                                                      Exceptional! 5.0/5
                                                                      (18 reviews)
                                                                      avg/night
                                                                      • 5 BR
                                                                      • 5 BA
                                                                      • Sleeps 14
                                                                      Villa #1654060
                                                                      18
                                                                      Viewed 60 times in the last 48 hours
                                                                        Wonderful! 4.8/5
                                                                        (25 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 7
                                                                        Multiple rentals Villa #401530
                                                                        25
                                                                        Viewed 40 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (32 reviews)
                                                                          avg/night
                                                                          • 3 BR
                                                                          • 3 BA
                                                                          • Sleeps 7
                                                                          Villa #294986
                                                                          32
                                                                          Viewed 120 times in the last 48 hours
                                                                            Exceptional! 5.0/5
                                                                            (50 reviews)
                                                                            avg/night
                                                                            • 3 BR
                                                                            • 3 BA
                                                                            • Sleeps 6
                                                                            Multiple rentals Villa #64960
                                                                            50
                                                                            Viewed 62 times in the last 48 hours
                                                                              Exceptional! 5.0/5
                                                                              (39 reviews)
                                                                              avg/night
                                                                              • 7 BR
                                                                              • 6 BA
                                                                              • Sleeps 14
                                                                              Villa #394760vb
                                                                              39
                                                                              Viewed 69 times in the last 48 hours
                                                                                Exceptional! 5.0/5
                                                                                (11 reviews)
                                                                                avg/night
                                                                                • 4 BR
                                                                                • 2 BA
                                                                                • Sleeps 8
                                                                                Villa #1674648
                                                                                11
                                                                                Viewed 22 times in the last 48 hours
                                                                                  • 7 BR
                                                                                  • 5 BA
                                                                                  • Sleeps 14
                                                                                  Villa #6564666
                                                                                  1
                                                                                    Exceptional! 5.0/5
                                                                                    (17 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 4
                                                                                    Multiple rentals Villa #91933
                                                                                    17
                                                                                    Viewed 11 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 12 times in the last 48 hours
                                                                                        Exceptional! 5.0/5
                                                                                        (85 reviews)
                                                                                        avg/night
                                                                                        • 3 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 6
                                                                                        Villa #95620
                                                                                        85
                                                                                        Viewed 29 times in the last 48 hours
                                                                                          • 3 BR
                                                                                          • 3 BA
                                                                                          • Separate Toilet
                                                                                          • Sleeps 8
                                                                                          Villa #872948
                                                                                          4
                                                                                          Viewed 26 times in the last 48 hours
                                                                                            • 4 BR
                                                                                            • 4 BA
                                                                                            • Sleeps 8
                                                                                            Villa #1931202
                                                                                            4
                                                                                            Viewed 37 times in the last 48 hours
                                                                                              avg/night
                                                                                              • 4 BR
                                                                                              • 4 BA
                                                                                              • Separate Toilet
                                                                                              • Sleeps 8
                                                                                              Villa #8123818
                                                                                              4
                                                                                              Viewed 11 times in the last 48 hours
                                                                                                Exceptional! 5.0/5
                                                                                                (10 reviews)
                                                                                                avg/night
                                                                                                • 6 BR
                                                                                                • 6 BA
                                                                                                • Separate Toilet
                                                                                                • Sleeps 13
                                                                                                Villa #3808832
                                                                                                10
                                                                                                Viewed 20 times in the last 48 hours
                                                                                                  Exceptional! 5.0/5
                                                                                                  (8 reviews)
                                                                                                  avg/night
                                                                                                  • 6 BR
                                                                                                  • 5 BA
                                                                                                  • Sleeps 12
                                                                                                  Multiple rentals Villa #76109
                                                                                                  8
                                                                                                  Viewed 60 times in the last 48 hours
                                                                                                    • 5 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 14
                                                                                                    Multiple rentals Villa #1894871
                                                                                                    1
                                                                                                    Viewed 21 times in the last 48 hours
                                                                                                      • 6 BR
                                                                                                      • 5 BA
                                                                                                      • Sleeps 12
                                                                                                      Villa #783398vb
                                                                                                      2
                                                                                                      Viewed 5 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      It's a beautiful property and does not disappoint.

                                                                                                      5 of 5
                                                                                                      We absolutely loved our stay at Club Monticello. We arrived late and had a nice welcome basket waiting on us with food and wine. The villa is very nice and fully equipped with anything you might need. The owners James and Penny were great and continued to spoil us with more wine and goodies. We used the concierge Rita and she helped set up the perfect tours, dinner reservations and cooking classes. The cooking class with Andrea was very fun for our entire family and the food was amazing. The location of the vineyard to Siena and Florence was great! We highly recommend and will definitely look to go visit again. You will not be disappointed.
                                                                                                      • Review Submitted: 04-Jan-2017
                                                                                                      • Date of Stay: Dec 2016

                                                                                                      Paradise in Tuscany!

                                                                                                      5 of 5
                                                                                                      We stayed at this stunning villa for 6 nights and were blown away. The pictures are nice but the villa itself has to be seen to be believed. We were 2 couples and we stayed in the 3 bedroom upstairs apartment and absolutely loved it. Less than a half hour from Sienna and about 1 hour from many popular destinations (San Gimignano, Montalcino, Montepulciano), we really had the time of our lives. We decided to take the italian cooking class with Enzo (the owner of the villa) and his 2 sons (Duccio and Max) and it was a night to remember. The sweetest people you can imagine and just mouth watering food and wine. They come to the villa, prepare their class, and then treat you to a 4 course meal of typical Tuscan cuisine. Definitely a highlight of our trip. Needless to say, we 100% recommend the villa. Romantic getaway, family vacation, travelling with friends, it's the perfect place to go. We were given a tour of the 2 bedroom apartment at the ground floor, equally stunning but we liked the fact that the upstairs had more than 1 bathroom. We left the villa with heavy hearts but I am certain that we will return one day. Can't wait!
                                                                                                      • Review Submitted: 01-Dec-2016
                                                                                                      • Date of Stay: Nov 2016

                                                                                                      UNFORGETTABLE!

                                                                                                      5 of 5
                                                                                                      This was a trip of a lifetime. The spectacular views, the rustic Barn, the food, the wine, the people, and of course Serena made it unforgettable. We hope to make the visit to Tuscany and The Barn a new Thanksgiving tradition. The property was exactly as described on the website and viewed in the pictures. It was very clean and well maintained. The house had everything you needed from pots and pans to umbrellas, espresso maker, tea kettle, spices even sporting equipment. There's even thyme and rosemary growing around the property. I highly recommend this property to anyone looking to make unforgettable memories with friends and family. Oh, one more plus, each bedroom has its own bathroom!
                                                                                                      • Review Submitted: 28-Nov-2016
                                                                                                      • Date of Stay: Nov 2016