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Gaiole in Chianti: Apartments, Villas & More (300+)

  • 1 - 50 of 300+
Additional fees apply. Taxes may be added.
    Exceptional! 5.0/5
    (48 reviews)
    avg/night
    • 3 BR
    • 3 BA
    • Sleeps 6
    Multiple rentals Villa #64960
    48
    Viewed 17 times in the last 48 hours
      • 1 BR
      • 1 BA
      • Sleeps 4
      Villa #654136vb
      4
      Viewed 14 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 6 times in the last 48 hours
          • 2 BR
          • 1 HF BA
          • Sleeps 4
          Cottage #1301990
          3
            • 1 BR
            • 1 BA
            • Sleeps 4
            Multiple rentals Apartment #38930
            3
              • 2 BR
              • 1 BA
              • 1 HF BA
              • Sleeps 6
              Multiple rentals House #38930
              4
                • 1 BR
                • Sleeps 3
                Apartment #2448656
                  Exceptional! 5.0/5
                  (6 reviews)
                  avg/night
                  • 1 BR
                  • Sleeps 3
                  Chateau / Country House #2031854
                  6
                  Viewed 5 times in the last 48 hours
                    • 7 BR
                    • 6 BA
                    • 1 HF BA
                    • Sleeps 16
                    Villa #3219134
                    4
                      • 1 BR
                      • 1 BA
                      • Sleeps 2
                      Multiple rentals Villa #6721451
                        • 1 BR
                        • 1 BA
                        • Sleeps 2
                        Multiple rentals Villa #6721451
                          • 2 BR
                          • 2 BA
                          • Sleeps 4
                          Multiple rentals Villa #6721451
                            • 1 BR
                            • 1 BA
                            • Sleeps 3
                            Multiple rentals Villa #6721451
                              • 1 BR
                              • 1 BA
                              • Sleeps 3
                              Multiple rentals Villa #6721451
                                • 3 BR
                                • Sleeps 6
                                Villa #1150760
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 5
                                  Multiple rentals Villa #79371
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 4
                                    Multiple rentals Villa #79371
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 3
                                      Multiple rentals Apartment #79371
                                      1 Review
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 4
                                        Multiple rentals Villa #79371
                                        2 Reviews
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 3
                                          Multiple rentals Villa #79371
                                            Excellent! 4.6/5
                                            (13 reviews)
                                            $71
                                            avg/night
                                            • 2 BR
                                            • 1 BA
                                            • 1 HF BA
                                            • Sleeps 4
                                            Apartment #8035722
                                            13
                                            Viewed 25 times in the last 48 hours
                                              Wonderful! 4.8/5
                                              (19 reviews)
                                              $89
                                              avg/night
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 2
                                              Castle #825856
                                              19
                                              Viewed 21 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (40 reviews)
                                                $60
                                                avg/night
                                                • 1 BR
                                                • 1 BA
                                                • Sleeps 3
                                                Apartment #6423320
                                                40
                                                Viewed 18 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 8 times in the last 48 hours
                                                    Wonderful! 4.9/5
                                                    (38 reviews)
                                                    avg/night
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 6
                                                    Apartment #485305vb
                                                    38
                                                    Viewed 13 times in the last 48 hours
                                                      Wonderful! 4.9/5
                                                      (21 reviews)
                                                      avg/night
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 4
                                                      Apartment #619692vb
                                                      21
                                                      Viewed 11 times in the last 48 hours
                                                        Wonderful! 4.9/5
                                                        (8 reviews)
                                                        avg/night
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 2
                                                        Castle #3878711
                                                        8
                                                        Viewed 5 times in the last 48 hours
                                                          Exceptional! 5.0/5
                                                          (9 reviews)
                                                          avg/night
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 4
                                                          Apartment #896240vb
                                                          9
                                                          Viewed 25 times in the last 48 hours
                                                            $58
                                                            avg/night
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 2
                                                            Apartment #6815893
                                                            1 Review
                                                            Viewed 12 times in the last 48 hours
                                                              $97
                                                              avg/night
                                                              • 2 BR
                                                              • 1 BA
                                                              • Sleeps 5
                                                              Apartment #6831648
                                                              Viewed 19 times in the last 48 hours
                                                                $89
                                                                avg/night
                                                                • 3 BR
                                                                • 2 BA
                                                                • Sleeps 6
                                                                Apartment #6844158
                                                                Viewed 8 times in the last 48 hours
                                                                  Wonderful! 4.9/5
                                                                  (7 reviews)
                                                                  avg/night
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 4
                                                                  Multiple rentals Apartment #489852
                                                                  7
                                                                  Viewed 5 times in the last 48 hours
                                                                    Excellent! 4.7/5
                                                                    (6 reviews)
                                                                    avg/night
                                                                    • 5 BR
                                                                    • 4 BA
                                                                    • Sleeps 11
                                                                    Multiple rentals Villa #76109
                                                                    6
                                                                    Viewed 9 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 78 times in the last 48 hours
                                                                        • Studio
                                                                        • 1 BA
                                                                        • Sleeps 2
                                                                        Multiple rentals House #76109
                                                                        3
                                                                        Viewed 5 times in the last 48 hours
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 8
                                                                          Multiple rentals Apartment #489852
                                                                          4
                                                                            • 5 BR
                                                                            • 5 BA
                                                                            • Sleeps 11
                                                                            Villa #6556510
                                                                              Excellent! 4.7/5
                                                                              (22 reviews)
                                                                              $59
                                                                              avg/night
                                                                              • 1 BR
                                                                              • Sleeps 4
                                                                              House #6366337
                                                                              22
                                                                              Viewed 5 times in the last 48 hours
                                                                                Wonderful! 4.9/5
                                                                                (55 reviews)
                                                                                $75
                                                                                avg/night
                                                                                • 2 BR
                                                                                • Sleeps 5
                                                                                Apartment #6579949
                                                                                55
                                                                                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
                                                                                  Viewed 5 times in the last 48 hours
                                                                                    Excellent! 4.4/5
                                                                                    (7 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 1 HF BA
                                                                                    • Sleeps 6
                                                                                    Apartment #6379067
                                                                                    7
                                                                                    Viewed 6 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 22 times in the last 48 hours
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 7
                                                                                        Villa #1363507
                                                                                        4
                                                                                          $61
                                                                                          avg/night
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          Apartment #859545vb
                                                                                          1 Review
                                                                                          Viewed 12 times in the last 48 hours
                                                                                            Wonderful! 4.9/5
                                                                                            (7 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 4
                                                                                            Apartment #6738764
                                                                                            7
                                                                                            Viewed 8 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (36 reviews)
                                                                                              $92
                                                                                              avg/night
                                                                                              • 3 BR
                                                                                              • Sleeps 5
                                                                                              Apartment #6594701
                                                                                              36
                                                                                              Viewed 12 times in the last 48 hours
                                                                                                avg/night
                                                                                                • 5 BR
                                                                                                • 5 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 10
                                                                                                Villa #1097226
                                                                                                4
                                                                                                Viewed 20 times in the last 48 hours
                                                                                                  • 3 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 7
                                                                                                  Chateau / Country House #1225354
                                                                                                  32
                                                                                                    Wonderful! 4.9/5
                                                                                                    (36 reviews)
                                                                                                    avg/night
                                                                                                    • 2 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 4
                                                                                                    Apartment #627686vb
                                                                                                    36
                                                                                                    Viewed 10 times in the last 48 hours
                                                                                                    • 1 - 50 of 300+
                                                                                                     

                                                                                                    Recent Gaiole in Chianti Reviews

                                                                                                    Quattro Torra - Rocambolesco

                                                                                                    5 of 5
                                                                                                    Our stay in the Castello delle quattro torri, was absolutely amazing; a "rocambolesco" experience! We were met at the door by Nicola on our first day. From the moment we waited for him before entering the castle doors, it felt like we were traveling back in time. The castle is incredibly beautiful. We arrived here later in the afternoon during the magic hour of the sun; the sun was shining on the castle, the colors of the leaves were changing on the vines of the castle walls. It was just stunning. Nicola welcomed us into his family's home as if we were old family and friends. Nicola couldn't have been more helpful and attentive to our every needs. He showed us the best place to park our rental car in Sienna, which was a five minute drive (literally - no more than four or five min) to Sienna. It's a family run business. The adorable woman (I think it was his Aunt) cooking us breakfast in the mornings was so sweet and the breakfast she made us was wonderful and authentic Italian (including cappuccinos!) The rooms were immaculate and beautifully decorated. The tower room we stayed in for one night had a neat spiral staircase leading up into the sleeping area. The view from the castle (bedrooms, living room, dining area) is amazing. You can see the Tuscan hills for miles. The land around the castle is so picturesque and you are encouraged to walk this entire area, walking through the olive groves and walking through the vineyards. It feels like you are in the scene of a movie. Nicola's family owns a farm nearby the castle with a restaurant on the property called Le Pietre Vive restaurant. One of the nights, we had the most "cena deliziosa" delicious dinner. Mauro, our waiter at the restaurant was super helpful with the menu, gave the best recommendations and even shared grappa with us! Nicola also makes his own chianti wine, saffron, honey and oil. We purchased wine and honey from Nicola to take back home with us. Nicola noticed it was my husband's birthday, while we were checking in, and the next morning, on his birthday, he greeted my husband with an Italian happy birthday and so did his Aunt. We absolutely loved our stay here at Castello delle Quattro Torra and would recommend it to everyone. Sienna is an incredible little city and the quick drive from there also makes it so wonderful. Thank you so much, Nicola! Grazie Mille! Love, Nicola & Tanya
                                                                                                    • Submitted: Dec 3, 2016
                                                                                                    • Stayed: Oct 2016

                                                                                                    Excellent host and lovely location!

                                                                                                    5 of 5
                                                                                                    My family stayed at Sandra's place in October. Sandra was very helpful in providing directions to her apartment. The apartment is in a great location right by the city wall. Walk-able to the City Center and all other major attractions. Sandra was great to deal with. She went over all the instructions thoroughly and you really felt like she wanted you to be comfortable and enjoy your stay. The apartment was very spacious and comfortable. It had very nice courtyard and patio and is very secure. There's a nice pizza place and other restaurants just on the corner. We would definitely stay again!
                                                                                                    • Submitted: Dec 3, 2016
                                                                                                    • Stayed: Oct 2016

                                                                                                    Wonderful Week

                                                                                                    5 of 5
                                                                                                    We (four of us) stayed for a week in early November. The villa is lovely with a fantastic location and breathtaking scenery. We did need the rental car, but distances to the surrounding towns are not great. The villa is beautifully equipped, especially the kitchen, and the whole house is immaculate. Francesca cooked two delicious and wonderfully Tuscan dinners for us. She was so friendly and we all felt very welcome. We would definitely stay here again!
                                                                                                    • Submitted: Nov 16, 2016
                                                                                                    • Stayed: Oct 2016