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Make a holiday rental home or villa in Val di Chiana, Italy your home away from home

Val di Chiana, Tuscany, lies just south of Arezzo, is named after the River Chiana which runs through the bottom of the valley. Reclaimed from the bed of a large lake, the Val di Chiana is an important communications route between Arezzo and Siena, yet the few villages which adorn the valley side are completely timeless, consisting of traditional brick cottages and thin, steep cobbled streets. The area is considered to be one of the most unspoilt rural regions in the whole of Europe, where large forests break only for idyllic mountain streams and picturesque medieval walled towns.

Things to do on holiday in Val di Chiana, Italy

The prehistoric caves of Monte Cetona are well worth a visit if you are staying in a self catering Val di Chiana property. They are adorned in fascinating pre-historic ‘graffiti’ which inspires visitors. The area is also known as having the best preserved network of 6th and 7th Century castles in Northern Italy, of which the Castle of Civitella di Val di Chiana. There are also a huge number of museums, archaeological museums, historical centres and monuments which keep the historical heritage of the region alive.

The Val di Chiana incorporates on of the most important thermal basins in Italy, and therefore those looking to enjoy the therapeutic, healing properties of Val di Chiana thermal waters flock to the region.

The stunning rural scenery which surrounds the villas and holiday homes in Val di Chiana is perfect for walking, cycling and horse riding. You can travel for many hours and not come across a road or town, stumbling across breath-taking views and charming secluded spots to pause and catch your breath. Taking a fishing rod is also an excellent option from a Val di Chiana holiday rental, although a permit is needed.

During the summer, the coast, which is just a few kilometres from the Val di Chiana, is a great place to sail or simply enjoy the sandy beaches of Tuscany.

Places to holiday in Val di Chiana, Italy

The most important town in the Val di Chiana is Montepulciano, an ancient walled town whose Renaissance centrepiece, the Piazza Grande, is surrounded by tiny streets and narrow alleyways. Much of the town was designed by distinguished local artists, and is well worth the visiting from ant of the Val di Chiana holiday rentals available.

Chianaciano is an enchanting town, which is divided into two halves. The medieval centre on top of the hill has managed to preserve its architecture and charm. Surrounding the centre is the more modern spa town. The therapeutic thermal springs which have risen to fame in Tuscany are surrounded by beautiful countryside, and attract over a million visitors to indulge in the warm spring waters.

Weather in Val di Chiana, Italy

Summer temperatures in Val di Chiana are blissfully warm, remaining at around 23°C in July and August. Even during the winter, temperatures are unlikely to drop below 10°C.

Flights to Val di Chiana, Italy

Depending on the exact location of your Val di Chiana property, either Pisa Airport (PSA), Florence (FLR) or Perugia Airport (PEG) will be the closest. RyanAir provide some very cheap flights to these three, and there are car hire facilities to be found at all three too.

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  • Showing 1-50 of 300+
Additional service fee may apply.
    Exceptional! 5.0/5
    (71 reviews)
    avg/night
    • 3 BR
    • 2 BA
    • Sleeps 6
    Chateau / Country House #436049vb
    71
    Viewed 9 times in the last 48 hours
      Exceptional! 5.0/5
      (9 reviews)
      avg/night
      • 5 BR
      • 5 BA
      • Sleeps 12
      Villa #1812215
      9
      Viewed 11 times in the last 48 hours
        Wonderful! 4.9/5
        (131 reviews)
        avg/night
        • 8 BR
        • 8 BA
        • Separate Toilet
        • Sleeps 16
        Villa #388827
        131
        Viewed 22 times in the last 48 hours
          Exceptional! 5.0/5
          (8 reviews)
          avg/night
          • 9 BR
          • 8 BA
          • Sleeps 31
          Villa #6738797
          8
          Viewed 21 times in the last 48 hours
            • 6 BR
            • 4 BA
            • Sleeps 12
            Villa #6790455
            Viewed 12 times in the last 48 hours
              • 5 BR
              • 3 BA
              • Sleeps 10
              Villa #1629633
              12
                • 9 BR
                • 8 BA
                • Sleeps 20
                Villa #1845028
                  • 7 BR
                  • 7 BA
                  • Separate Toilet
                  • Sleeps 16
                  Farmhouse #1150802
                  1 Review
                    • 6 BR
                    • 6 BA
                    • Separate Toilet
                    • Sleeps 14
                    Villa #1844992
                      • 5 BR
                      • 4 BA
                      • Sleeps 10
                      Villa #6739918
                      3
                        • 3 BR
                        • 3 BA
                        • Sleeps 6
                        Villa #1845048
                          • 4 BR
                          • 4 BA
                          • Sleeps 9
                          Villa #1633045
                          1 Review
                            • 5 BR
                            • 6 BA
                            • Sleeps 10
                            House #1018668
                              • 2 BR
                              • 2 BA
                              • Separate Toilet
                              • Sleeps 6
                              Apartment #890701vb
                                • 6 BR
                                • 5 BA
                                • Separate Toilet
                                • Sleeps 12
                                Villa #1150695
                                  • 4 BR
                                  • 5 BA
                                  • Sleeps 8
                                  Villa #1150779
                                    • 4 BR
                                    • 5 BA
                                    • Sleeps 10
                                    Villa #1150741
                                      • 4 BR
                                      • 3 BA
                                      • Sleeps 9
                                      Villa #1150776
                                        • 6 BR
                                        • 6 BA
                                        • Sleeps 12
                                        Villa #1150907
                                          • 3 BR
                                          • 3 BA
                                          • Separate Toilet
                                          • Sleeps 6
                                          Villa #1150917
                                            • 6 BR
                                            • 6 BA
                                            • Sleeps 6
                                            Villa #1194128
                                              • 7 BR
                                              • 6 BA
                                              • Sleeps 14
                                              Villa #1844999
                                                • 5 BR
                                                • 7 BA
                                                • Sleeps 10
                                                Villa #1908361
                                                  avg/night
                                                  • 5 BR
                                                  • 4 BA
                                                  • Sleeps 9
                                                  Villa #6109674
                                                  Viewed 36 times in the last 48 hours
                                                    Wonderful! 4.8/5
                                                    (5 reviews)
                                                    avg/night
                                                    • 14 BR
                                                    • 11 BA
                                                    • Sleeps 34
                                                    Villa #92792
                                                    5
                                                    Viewed 27 times in the last 48 hours
                                                      Exceptional! 5.0/5
                                                      (67 reviews)
                                                      avg/night
                                                      • 6 BR
                                                      • 4 BA
                                                      • Sleeps 12
                                                      Villa #97774
                                                      67
                                                      Viewed 6 times in the last 48 hours
                                                        avg/night
                                                        • 4 BR
                                                        • 4 BA
                                                        • Sleeps 9
                                                        Villa #6027548
                                                        Viewed 11 times in the last 48 hours
                                                          • Studio
                                                          • 1 BA
                                                          • Sleeps 3
                                                          Multiple rentals Apartment #6310027
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 4
                                                            Multiple rentals Apartment #6310027
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 4
                                                              Multiple rentals Apartment #6310027
                                                                • 4 BR
                                                                • 5 BA
                                                                • Sleeps 12
                                                                Multiple rentals Apartment #6310027
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 2
                                                                  Chateau / Country House #1107353
                                                                  33
                                                                    Exceptional! 5.0/5
                                                                    (11 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    Multiple rentals Farmhouse #1612507
                                                                    11
                                                                    Viewed 10 times in the last 48 hours
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 2
                                                                      Multiple rentals Farmhouse #1612507
                                                                      Viewed 5 times in the last 48 hours
                                                                        • 7 BR
                                                                        • 6 BA
                                                                        • Sleeps 14
                                                                        Villa #4085885
                                                                          • 8 BR
                                                                          • 7 BA
                                                                          • Sleeps 18
                                                                          Villa #442376
                                                                          1 Review
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Sleeps 6
                                                                            Apartment #615969vb
                                                                            19
                                                                              Wonderful! 4.9/5
                                                                              (47 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 7
                                                                              Apartment #6066867
                                                                              47
                                                                                Exceptional! 5.0/5
                                                                                (13 reviews)
                                                                                avg/night
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 6
                                                                                Apartment #1017638
                                                                                13
                                                                                Viewed 9 times in the last 48 hours
                                                                                  • 3 BR
                                                                                  • 3 BA
                                                                                  • Separate Toilet
                                                                                  • Sleeps 6
                                                                                  Villa #981324
                                                                                  34
                                                                                    • 2 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 6
                                                                                    Chateau / Country House #1649482
                                                                                    4
                                                                                      Excellent! 4.7/5
                                                                                      (14 reviews)
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 5
                                                                                      Cottage #6300494
                                                                                      14
                                                                                        Exceptional! 5.0/5
                                                                                        (26 reviews)
                                                                                        avg/night
                                                                                        • 4 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 10
                                                                                        Villa #6415307
                                                                                        26
                                                                                        Viewed 9 times in the last 48 hours
                                                                                          Wonderful! 4.9/5
                                                                                          (31 reviews)
                                                                                          avg/night
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          Multiple rentals Apartment #6432643
                                                                                          31
                                                                                            Excellent! 4.7/5
                                                                                            (14 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 6
                                                                                            Multiple rentals Apartment #6432643
                                                                                            14
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              Multiple rentals Apartment #422892
                                                                                              4
                                                                                                • 2 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 7
                                                                                                Multiple rentals Cottage #422892
                                                                                                1 Review
                                                                                                  • Studio
                                                                                                  • 1 BA
                                                                                                  • Sleeps 3
                                                                                                  Multiple rentals Apartment #422892
                                                                                                  2 Reviews
                                                                                                  • 1 - 50 of 300+
                                                                                                   

                                                                                                  Recent Reviews

                                                                                                  Beautiful grounds and comfortable villa

                                                                                                  5 of 5
                                                                                                  My family and I had a wonderful time in your beautiful villa and we were astonished by its size, location and atmosphere - it fully lived up to our expectations. At the first glance of the house we thought we had taken the wrong exit – and couldn’t believe that this was actually the villa in which we would spend a whole week. It was fantastic, beautiful grounds, geat views on sweet hills, amazing swimming pool, gorgeous villa. it had everything and superb value as well. We had more then enough space and everybody was extremely comfortable, especially the kids. The location is fantastic as well, close to the lake, the village, major tuscan cities and of course Montepulciano and Cortona. Finally it's worth mentioning the hosts are always on hand to help with any queries or resolving problems, they understand perfectly well your needs and nothing is too much trouble for them. I would recommend wholeheartedly!
                                                                                                  • Review Submitted: 24-Nov-2016
                                                                                                  • Date of Stay: Sep 2016

                                                                                                  Lovely rustic farmhouse with plenty of peace and quiet

                                                                                                  4 of 5
                                                                                                  Cetona is well placed for visiting Southern Tuscany and cities like Siena. There is plenty to do and the town itself is charming. Homely and comfortable house with plenty of space. Hope to return one day.
                                                                                                  • Review Submitted: 31-Oct-2016
                                                                                                  • Date of Stay: Oct 2016

                                                                                                  PERFECTION IN EVERY WAY IMAGINABLE!

                                                                                                  5 of 5
                                                                                                  Our stay at Villa Le Caggiole far exceeded our high expectations. No superlatives can do it justice! Everything was absolutely perfect -- from the warm and attentive hosting by Francesca throughout the week, to the beautiful, immaculate and comfortable accommodations, and to the spectacular views of the vineyard, olive orchard and expansive countryside below. Easy and convenient access into nearby Montepulciano and other ancient hilltop villages such as Pienza and Cortona. Highly recommended without hesitation to anyone seeking a private and relaxing retreat in the heart of Tuscany. We would give it six stars if we could!
                                                                                                  • Review Submitted: 06-Oct-2016
                                                                                                  • Date of Stay: Sep 2016