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
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!

Montescudaio: Apartments, Villas & More (300+)

  • 1 - 50 of 300+
Additional fees apply. Taxes may be added.
    • 1 BR
    • Sleeps 4
    Apartment #6686543
      • 2 BR
      • Sleeps 6
      Apartment #6362280
        • 3 BR
        • 2 BA
        • Sleeps 6
        Multiple rentals Chateau / Country House #545999
        11
          • 2 BR
          • 1 BA
          • Sleeps 5
          Multiple rentals Farmhouse #641149
          2
            • 1 BR
            • 1 BA
            • Sleeps 4
            Multiple rentals Apartment #641149
            1
              • 2 BR
              • 1 BA
              • Sleeps 5
              Multiple rentals Chateau / Country House #545999
              7
              Viewed 9 times in the last 48 hours
                • 2 BR
                • 1 BA
                • Sleeps 6
                Multiple rentals Chateau / Country House #641149
                2
                  • 2 BR
                  • 1 BA
                  • 1 HF BA
                  • Sleeps 5
                  Chateau / Country House #1687247
                  2
                    • 1 BR
                    • 1 BA
                    • Sleeps 2
                    Apartment #1407641
                    9
                      • 2 BR
                      • 1 BA
                      • Sleeps 4
                      Multiple rentals Cottage #641149
                        • 3 BR
                        • 2 BA
                        • Sleeps 7
                        Multiple rentals Cottage #641149
                          • 2 BR
                          • 2 BA
                          • Sleeps 5
                          Multiple rentals Apartment #641149
                            • 2 BR
                            • 2 BA
                            • Sleeps 6
                            Chateau / Country House #1731423
                              • 1 BR
                              • 1 BA
                              • Sleeps 4
                              Apartment #2462419
                                • 4 BR
                                • 2 BA
                                • Sleeps 12
                                Villa #8053457
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 5
                                  Apartment #2462420
                                    Excellent! 4.7/5
                                    (12 reviews)
                                    $57
                                    avg/night
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 6
                                    House #53601
                                    12
                                    Viewed 15 times in the last 48 hours
                                      Exceptional! 5.0/5
                                      (5 reviews)
                                      $60
                                      avg/night
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 4
                                      Multiple rentals Apartment #8125211
                                      5
                                      Viewed 10 times in the last 48 hours
                                        Wonderful! 4.9/5
                                        (66 reviews)
                                        $42
                                        avg/night
                                        • 1 BR
                                        • 1 HF BA
                                        • Sleeps 5
                                        House #6162521
                                        66
                                          Excellent! 4.7/5
                                          (7 reviews)
                                          $55
                                          avg/night
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 6
                                          Multiple rentals Apartment #6377140
                                          7
                                          Viewed 6 times in the last 48 hours
                                            Exceptional! 5.0/5
                                            (19 reviews)
                                            $92
                                            avg/night
                                            • 1 BR
                                            • 1 BA
                                            • Sleeps 4
                                            Apartment #1104241
                                            19
                                            Viewed 5 times in the last 48 hours
                                              Exceptional! 5.0/5
                                              (11 reviews)
                                              $97
                                              avg/night
                                              • 2 BR
                                              • 1 BA
                                              • Sleeps 4
                                              Cottage #1207142
                                              11
                                              Viewed 14 times in the last 48 hours
                                                Excellent! 4.6/5
                                                (7 reviews)
                                                avg/night
                                                • 4 BR
                                                • 3 BA
                                                • 1 HF BA
                                                • Sleeps 8
                                                Villa #1444369
                                                7
                                                Viewed 10 times in the last 48 hours
                                                  Exceptional! 5.0/5
                                                  (7 reviews)
                                                  avg/night
                                                  • 3 BR
                                                  • 1 BA
                                                  • 1 HF BA
                                                  • Sleeps 7
                                                  House #754550
                                                  7
                                                  Viewed 18 times in the last 48 hours
                                                    avg/night
                                                    • 3 BR
                                                    • 3 BA
                                                    • Sleeps 8
                                                    House #2399691
                                                    Viewed 12 times in the last 48 hours
                                                      avg/night
                                                      • 4 BR
                                                      • 2 BA
                                                      • 1 HF BA
                                                      • Sleeps 10
                                                      Chateau / Country House #1890995
                                                      Viewed 10 times in the last 48 hours
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 4
                                                        House #1980329
                                                        3
                                                          $57
                                                          avg/night
                                                          • 2 BR
                                                          • 2 BA
                                                          • 1 HF BA
                                                          • Sleeps 6
                                                          Apartment #4255357
                                                          2
                                                          Viewed 23 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (8 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 1 BA
                                                            • Sleeps 5
                                                            Villa #323419vb
                                                            8
                                                            Viewed 25 times in the last 48 hours
                                                              • 2 BR
                                                              • Sleeps 6
                                                              Chateau / Country House #6643924
                                                              2
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 4
                                                                Chateau / Country House #6542271
                                                                1
                                                                Viewed 7 times in the last 48 hours
                                                                  Exceptional! 5.0/5
                                                                  (22 reviews)
                                                                  $75
                                                                  avg/night
                                                                  • 1 BR
                                                                  • Sleeps 5
                                                                  House #6184925
                                                                  22
                                                                  Viewed 19 times in the last 48 hours
                                                                    • 1 BR
                                                                    • Sleeps 2
                                                                    Studio #6447948
                                                                    1
                                                                      avg/night
                                                                      • 5 BR
                                                                      • 6 BA
                                                                      • Sleeps 11
                                                                      Villa #1572064
                                                                      3
                                                                      Viewed 12 times in the last 48 hours
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 7
                                                                        Apartment #2464005
                                                                          Exceptional! 5.0/5
                                                                          (7 reviews)
                                                                          $63
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 4
                                                                          Apartment #6506296
                                                                          7
                                                                          Viewed 19 times in the last 48 hours
                                                                            $53
                                                                            avg/night
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Sleeps 6
                                                                            Apartment #6562474
                                                                            Viewed 9 times in the last 48 hours
                                                                              • 8 BR
                                                                              • 9 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 26
                                                                              Chateau / Country House #428261
                                                                              3
                                                                                Wonderful! 4.9/5
                                                                                (71 reviews)
                                                                                $91
                                                                                avg/night
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                Apartment #305388vb
                                                                                71
                                                                                Viewed 24 times in the last 48 hours
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  Multiple rentals Apartment #8125211
                                                                                  3
                                                                                  Viewed 7 times in the last 48 hours
                                                                                    Exceptional! 5.0/5
                                                                                    (47 reviews)
                                                                                    $46
                                                                                    avg/night
                                                                                    • 1 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    House #6621471
                                                                                    47
                                                                                    Viewed 9 times in the last 48 hours
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 4
                                                                                      Apartment #2399675
                                                                                      9
                                                                                        avg/night
                                                                                        • 9 BR
                                                                                        • 9 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 18
                                                                                        Villa #6843957
                                                                                        Viewed 7 times in the last 48 hours
                                                                                          • 5 BR
                                                                                          • 5 BA
                                                                                          • Sleeps 10
                                                                                          Villa #6895841
                                                                                            • 2 BR
                                                                                            • Sleeps 6
                                                                                            Apartment #6440411
                                                                                              Wonderful! 4.9/5
                                                                                              (18 reviews)
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 4
                                                                                              House #457584vb
                                                                                              18
                                                                                              Viewed 27 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (15 reviews)
                                                                                                $76
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 4
                                                                                                House #2443642
                                                                                                15
                                                                                                Viewed 9 times in the last 48 hours
                                                                                                • 1 - 50 of 300+
                                                                                                 

                                                                                                Recent Montescudaio Reviews

                                                                                                Meet your new Italian family

                                                                                                5 of 5
                                                                                                At first glance of the reviews, this b&b seemed to good to be true. It definitely lived up to all the hype and much, much more. Andrea and Lucia are incredibly sweet, kind and wonderfully caring and attentive hosts. Their home is so beautiful and has some of the most amazing views in Tuscany. It makes the drive there worth it. When driving to their home, you'll notice the amazing Tuscan views of the olive trees and vineyards in a 360 view. Upon reaching the mailboxes on the road to their home in Tavarnelle, you'll most likely be greeted by Andrea who paitiently waits with excitement for his guests to arrive or looking for his adorable dogs Pascha and Luna. They are just perfect. We loved that you immediately feel immersed in italian culture in this area. Their home is wonderful; you hear the roosters in the morning from your second floor room window. The room is perfectly sized, beautifully decorated and very cozy. The bathroom is better than a five star hotel. The dinner they cooked for us was incredible and we were given a perfect Italian breakfast each morning. We had no issues communicating with them, even considering that we don't speak Italian. Their home is nearby other smaller towns and any winery you'd want to visit (we recommend Poggio al Bosco family owned). Bottom line, this is the best VRBO we have ever stayed in and we would recommend it to everyone. We loved meeting and getting to know you both, Andrea and Lucia. We hope to see you soon again!
                                                                                                • Submitted: Nov 10, 2016
                                                                                                • Stayed: Oct 2016

                                                                                                Nice garden, very close to the center and an amazing gentle host!

                                                                                                5 of 5
                                                                                                We stayed very close to the center of this beautiful city. Using their bikes we followed the hole citywall and visited the Dali exhibition. Paolo is a very gentle and helpfull person. We could eat the special grapes hanging just before are noses in the nice and great garden. Within half an hour we were at the airport by bus.
                                                                                                • Submitted: Oct 27, 2016
                                                                                                • Stayed: Oct 2016

                                                                                                Picture perfect vacation in the Tuscan countryside

                                                                                                5 of 5
                                                                                                Our family had a wonderful vacation at Villa Il Casolare! The house was beautifully renovated with modern and well-equipped kitchen and baths, while retaining its old world charm and character. It was clean, comfortable and the grounds and pool were well-cared for and truly lovely. We were there in late June/early July when the weather was warm and sunny. Despite the lack of AC, by closing up the house in the morning and then opening up the shutters and windows at night (the Tuscan way!), and using the fans provided, we were plenty cool and comfortable while we slept. The crystal clear pool was set amidst a grove of olive trees, and we spent many afternoons relaxing and reading under the shady canopy, in one of the many chairs and lounges. The location of Il Casolare was convenient to Florence (easy train ride), Siena, San Gimignano (both stunningly beautiful, medieval, walled cities) and even Cinque Terre - a bit longer drive, but well worth the visit! We found that interspersing a busier sightseeing day with a relaxing day at the villa made for an ideal vacation schedule. Eleonora, the owner, was warm, gracious and incredibly helpful to us as we planned our time in Italy. She generously helped me with train schedules, restaurant recommendations and reservations as well as local info and maps. She and Andrea even prepared a delicious meal one evening for us at the house; something that they offer and which I would highly recommend. They had a wonderful selection of wines available at the house, as well. As a family of runners, our efforts on the quiet and mostly shady roads around the villa were rewarded with breathtaking views at every bend. Most of all, we loved the loggia next to the house, with its stunning view of the countryside, including the distinct hill and towers of San Gimignano. We spent much time here reading, writing, sketching and enjoying breakfast, the occasional lunch and more dinners than we expected! Out of the 9 nights we spent there, more than half included dinner in this amazing spot. We made a trip to the local grocery store and market and found ingredients to supplement the thoughtful welcome basket provided to us by Eleonora. Some of our favorite memories include all of us in the kitchen, cooking up a delicious pasta feast and then dining outside, watching the sun go down, with a glass of wine! I would absolutely recommend this villa to my family and friends and will definitely plan a return visit!
                                                                                                • Submitted: Jul 17, 2016
                                                                                                • Stayed: Jun 2016