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  • Showing 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 12 times in the last 48 hours
      • 1 BR
      • 1 BA
      • Sleeps 4
      Villa #654136vb
      4
      Viewed 8 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 7 times in the last 48 hours
          • 2 BR
          • 1 HF BA
          • Sleeps 4
          Cottage #1301990
          3
          Viewed 6 times in the last 48 hours
            Very Good! 4.0/5
            (5 reviews)
            $83
            avg/night
            • 2 BR
            • 2 BA
            • Sleeps 4
            Cottage #696005vb
            5
            Viewed 7 times in the last 48 hours
              • 4 BR
              • 3 BA
              • Sleeps 10
              Villa #45144vb
              12
                • 1 BR
                • 1 BA
                • Sleeps 3
                Multiple rentals Chateau / Country House #454623
                1
                  avg/night
                  • 6 BR
                  • 4 BA
                  • Sleeps 12
                  Villa #8159492
                  1
                  Viewed 6 times in the last 48 hours
                    • 3 BR
                    • 2 BA
                    • Sleeps 5
                    Castle #1751580
                    2
                      • 2 BR
                      • 1 BA
                      • Sleeps 5
                      Multiple rentals Chateau / Country House #454623
                      1
                        • 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
                          Viewed 8 times in the last 48 hours
                            • 2 BR
                            • 1 BA
                            • Sleeps 5
                            Apartment #1680263
                              • 1 BR
                              • Sleeps 3
                              Apartment #2448656
                                • 3 BR
                                • 3 BA
                                • 1 HF BA
                                • Sleeps 7
                                Villa #908036
                                11
                                  • 1 BR
                                  • Sleeps 3
                                  Chateau / Country House #2031854
                                  6
                                    • 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
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        Multiple rentals Villa #79371
                                                        2
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 3
                                                          Multiple rentals Villa #79371
                                                            Excellent! 4.7/5
                                                            (22 reviews)
                                                            $59
                                                            avg/night
                                                            • 1 BR
                                                            • Sleeps 4
                                                            House #6366337
                                                            22
                                                            Viewed 9 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 16 times in the last 48 hours
                                                                • 3 BR
                                                                • 2 BA
                                                                • Sleeps 7
                                                                Apartment #6519075
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 4
                                                                  Multiple rentals Apartment #489852
                                                                  7
                                                                    Excellent! 4.7/5
                                                                    (6 reviews)
                                                                    avg/night
                                                                    • 5 BR
                                                                    • 4 BA
                                                                    • Sleeps 11
                                                                    Multiple rentals Villa #76109
                                                                    6
                                                                    Viewed 6 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 55 times in the last 48 hours
                                                                        • Studio
                                                                        • 1 BA
                                                                        • Sleeps 2
                                                                        Multiple rentals House #76109
                                                                        3
                                                                        Viewed 9 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
                                                                              Wonderful! 4.8/5
                                                                              (54 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 7
                                                                              Apartment #145257vb
                                                                              54
                                                                              Viewed 25 times in the last 48 hours
                                                                                Excellent! 4.6/5
                                                                                (13 reviews)
                                                                                $71
                                                                                avg/night
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 4
                                                                                Apartment #8035722
                                                                                13
                                                                                Viewed 40 times in the last 48 hours
                                                                                  Wonderful! 4.8/5
                                                                                  (49 reviews)
                                                                                  avg/night
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 6
                                                                                  Apartment #324072vb
                                                                                  49
                                                                                  Viewed 43 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 28 times in the last 48 hours
                                                                                      Wonderful! 4.9/5
                                                                                      (55 reviews)
                                                                                      $75
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • Sleeps 5
                                                                                      Apartment #6579949
                                                                                      55
                                                                                      Viewed 16 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 25 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 18 times in the last 48 hours
                                                                                              Wonderful! 4.9/5
                                                                                              (8 reviews)
                                                                                              avg/night
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 2
                                                                                              Castle #3878711
                                                                                              8
                                                                                              Viewed 10 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
                                                                                                  Viewed 12 times in the last 48 hours
                                                                                                    $97
                                                                                                    avg/night
                                                                                                    • 2 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 5
                                                                                                    Apartment #6831648
                                                                                                    Viewed 20 times in the last 48 hours
                                                                                                    • 1 - 50 of 300+

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

                                                                                                     

                                                                                                    Recent Gaiole in Chianti Reviews

                                                                                                    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

                                                                                                    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

                                                                                                    Apartment was lovely, exactly how one picture Tuscany. Steep incline leading to courtyard Yo walk,

                                                                                                    5 of 5
                                                                                                    Not suitable for elderly or those with trouble walking, as steep incline into courtyard, & flight of stone stairs into apartment. Great location. Can walk to everything in town. We'd stay here again
                                                                                                    • Submitted: Oct 24, 2016
                                                                                                    • Stayed: Oct 2016