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!

Gaiole in Chianti: Villa Rentals (1,530)

  • 1 - 50 of 300+
Additional fees apply. Taxes may be added.
    • 1 BR
    • 1 BA
    • Sleeps 4
    Villa #654136vb
    4
      • 3 BR
      • 3 BA
      • Sleeps 6
      Multiple rentals Villa #64960
      48
        • 2 BR
        • 1 BA
        • Sleeps 4
        Multiple rentals Villa #64960
        19
          • 9 BR
          • 5 BA
          • Sleeps 18
          Multiple rentals Villa #1140076
          16
            • 8 BR
            • 4 BA
            • Sleeps 16
            Villa #1934854
            5
              • 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
                                • 2 BR
                                • 1 BA
                                • Sleeps 4
                                Multiple rentals Villa #79371
                                2 Reviews
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 3
                                  Multiple rentals Villa #79371
                                    • 7 BR
                                    • Sleeps 14
                                    Villa #1004445
                                    2 Reviews
                                      • 5 BR
                                      • 6 BA
                                      • Sleeps 12
                                      Villa #281961vb
                                      29
                                        • 6 BR
                                        • 6 BA
                                        • 1 HF BA
                                        • Sleeps 13
                                        Villa #3808832
                                        10
                                          • 4 BR
                                          • 3 BA
                                          • Sleeps 10
                                          Villa #45144vb
                                          12
                                            • 3 BR
                                            • 3 BA
                                            • Sleeps 8
                                            Villa #829953
                                            7
                                              • 3 BR
                                              • 3 BA
                                              • 1 HF BA
                                              • Sleeps 7
                                              Villa #908036
                                              11
                                                • 3 BR
                                                • 3 BA
                                                • 1 HF BA
                                                • Sleeps 7
                                                Villa #8043542
                                                2 Reviews
                                                  • 5 BR
                                                  • 5 BA
                                                  • Sleeps 13
                                                  Villa #604892vb
                                                    • 6 BR
                                                    • 4 BA
                                                    • Sleeps 12
                                                    Villa #8159492
                                                    1 Review
                                                      • 4 BR
                                                      • 3 BA
                                                      • Sleeps 10
                                                      Villa #8042755
                                                      2 Reviews
                                                        • 6 BR
                                                        • 5 BA
                                                        • Sleeps 12
                                                        Multiple rentals Villa #76109
                                                        8
                                                          • 5 BR
                                                          • 4 BA
                                                          • Sleeps 11
                                                          Multiple rentals Villa #76109
                                                          6
                                                            • 5 BR
                                                            • 5 BA
                                                            • Sleeps 11
                                                            Villa #6556510
                                                              • 3 BR
                                                              • 3 BA
                                                              • Sleeps 6
                                                              Villa #1634641
                                                              2 Reviews
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 6
                                                                Villa #461335
                                                                2 Reviews
                                                                  • 5 BR
                                                                  • 3 BA
                                                                  • Sleeps 10
                                                                  Villa #8155527
                                                                  4
                                                                    • 6 BR
                                                                    • 5 BA
                                                                    • Sleeps 11
                                                                    Villa #1984292
                                                                      • 5 BR
                                                                      • 6 BA
                                                                      • Sleeps 12
                                                                      Villa #6482610
                                                                        • 5 BR
                                                                        • 6 BA
                                                                        • Sleeps 10
                                                                        Villa #6823385
                                                                          • 2 BR
                                                                          • 3 BA
                                                                          • Sleeps 6
                                                                          Villa #1755396
                                                                            • 5 BR
                                                                            • 5 BA
                                                                            • Sleeps 10
                                                                            Villa #6853180
                                                                              • 5 BR
                                                                              • 3 BA
                                                                              • Sleeps 15
                                                                              Villa #6893849
                                                                                • 4 BR
                                                                                • 3 BA
                                                                                • Sleeps 8
                                                                                Villa #1668306
                                                                                  • 5 BR
                                                                                  • 4 BA
                                                                                  • Sleeps 9
                                                                                  Villa #1619079
                                                                                  2 Reviews
                                                                                    • 5 BR
                                                                                    • 6 BA
                                                                                    • Sleeps 12
                                                                                    Villa #1778588
                                                                                    1 Review
                                                                                      • 6 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 12
                                                                                      Villa #6100383
                                                                                        • 6 BR
                                                                                        • 4 BA
                                                                                        • Sleeps 14
                                                                                        Villa #891102vb
                                                                                        2 Reviews
                                                                                          • 5 BR
                                                                                          • 6 BA
                                                                                          • Sleeps 10
                                                                                          Villa #6850174
                                                                                            • 5 BR
                                                                                            • 6 BA
                                                                                            • Sleeps 12
                                                                                            Villa #6853478
                                                                                              • 8 BR
                                                                                              • 6 BA
                                                                                              • Sleeps 16
                                                                                              Villa #6733010
                                                                                              • 1 - 50 of 300+
                                                                                               

                                                                                              Recent Gaiole in Chianti Reviews

                                                                                              Stunning views and amazing hosts, a truly Tuscan

                                                                                              5 of 5
                                                                                              A group of 17 of us rented out the entire place for 8 days. We had the best time exploring Chianti and Tuscany from Alberto and Camilla's wonderful villa! Between the all the space in the main house and the Hunting lodge, we never felt like we didn't have enough space. Both patios provided plenty of space to sit and amazing views. There are plenty of bathrooms for a large group and plenty of space to sit down for dinners and meals. The kitchens are fully stocked with what you need to cook, but come prepared with groceries unless you have a car. The closest town is a good 20 minute walk and there is hardly anything in there. If you rent a driver and bus, please note that getting down to the house is bumpy and steep, but possible. Do all of your shopping when you are visiting other towns and be prepared to cook dinners or have them cook dinners, the are no restaurants within in short walking distance. I would highly recommend the pizza by Alberto and any dinners by both of them. Everything they made was pure Tuscan heaven and memorable. Come hungry, they out due themselves. I would also recommend dinner at Dievole, a winery very close to them for one evening. Alberto and Camilla will make you feel so welcome and will make this trip a once in a lifetime experience. Camilla is a terrific guide and I would highly recommend booking her for a full day visit to Siena (a magical city). She also took us to Pienza and Montalcino, she is very knowledgeable and will provide an amazing guided tour. I highly recommend this location and house! The house itself is very comfortable, but slightly rustic. If you are looking for something modern or new, you will not find it here. The beds are comfortable, rooms are clean, and the space is great. I hope you can visit this part of Chianti/Tuscany!
                                                                                              • Submitted: Oct 24, 2016
                                                                                              • Stayed: Oct 2016

                                                                                              Tuscan Charm and Luxury

                                                                                              5 of 5
                                                                                              Looking forward to our Italian vacation, we knew with certainty we wanted 2 weeks in a villa which provided a tranquil escape, panoramic views of vineyards and rolling Tuscan hills in the horizon; we wanted to begin each day greeted by beautiful sunrises and ending with mesmerizing sunsets. In the villa itself, we wanted a stay in a Tuscan villa with rustic charm but complete with modern amenities for our convenience and comfort. To our delight Isola Serena surpassed our expectations! The villa was thoughtfully and strategically designed to complement the Tuscan landscape. The thoughtful design was illustrated through each window of the home which acted as frames for the surrounding landscape presenting it as living art, achieving the goal to remind us of the beauty surrounding the villa. As for our comfort and convenience, this same thoughtfulness was applied through the amenities both in and outside the home (kitchen, dining room, bedrooms, bathrooms, patio and pool). The only downside of Isola Serena is that we wanted to spend every moment possible in this picture-perfect home. It is worthwhile to mention the convenience of the location where the town of Castellina was less than ten minutes away. There was easy access to many other towns in the Chianti region, for a day trip to Florence or Siena, or a short drive to Montalcino to explore the Brunello region. Our stay was also made more relaxing by the ready availability of Natalia, the property manager, who was always willing to answer any questions or address any concerns. We have visited Italy numerous times and have rented a number of villas, many of which were beautiful homes with significant sentimentality attached, however we can attest that, for us, Isola Serena tops the list. To answer the common question when we consider renting a home away from home: ‘Do the pictures reflect the reality? Our emphatic response is the reality is much better!
                                                                                              • Submitted: Oct 4, 2016
                                                                                              • Stayed: Aug 2016

                                                                                              Absolutely wonderful visit!

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