HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.

Holidaymakers searching for holiday rentals in Chianti also enquired about villas in Cortona, villas in Macerata and apartments in San Gimignano

Make a holiday rental apartment or villa in Chianti, Tuscany, Italy your home away from home

An area of rolling hills and vineyard laden valleys, Chianti is a world famous section of the beautiful Province of Tuscany, Italy, famous for its wines. Situated between Florence and Siena, taking a Chianti villa rental not only puts you amongst the stunning rural scenery, surrounded by a selection of the best wines produced anywhere in the world, but also gives you access to some of the richest artistic heritage too. Self catering villas in Chianti, Tuscany, are a dream for wine connoisseurs everywhere.

Things to do in Chianti, Tuscany

The Tuscan countryside is ideal for exploration, by foot, on bicycle or, for those with a little less time or less energy, by car. Walking and cycling holidays using a Chianti rental villa are ideal, not only due to the idyllic setting and freedom provided, but also for the fact that there is very little that compares to the experience of sitting outside a self catering villa in Chianti, watching the sun set over the hills with a glass of local Chianti wine.

One of the nicest places to walk, relax and absorb the natural environment from a Chianti apartment rental or self catering villa is the Monte San Michele National Park, which lets you walk the hills to spectacular view points over hilltop towns and small vineyards bordered by woodland, well off the usual tourist trails.

Places to go on holiday in Chianti, Tuscany

Wine connoisseurs taking a villa in Chianti, Tuscany, will love Greve in September. Greve is the setting for the largest wine festival in Chianti, providing you the chance to sample, purchase and enjoy the huge variety of Chianti wines produced in the region.

San Casciano in the Val di Pesa is just 15km from Florence. San Casciano was a Roman outpost, and many of the old Roman villas, medieval fortresses and monasteries have now been turned into dramatic, luxury Chianti villas, overlooking the beautiful Val di Greve on one side and Val di Pesa to the other.

Impruneta is a rich, stately town bounded by the Florentine Hills and the rivers of both the Greve and Ema, with beautiful views and some magnificent restaurants and craft shops.

Weather in Chianti, Tuscany

Summers in Chianti are gloriously warm, with average daily temperatures from June until August of over 30°C, an average of 10°C higher than temperatures in the UK. Even during the winter, temperatures are over 10°C.

Travel to Chianti, Tuscany

Being ideally situated between Siena (SAY) and Florence (FLR) Airports, finding cheap flights to Chianti is easy, and reaching your self catering Chianti holiday villa is painless.

Cancel Clear Filters Apply Filters

Property Type

Popular Searches

Payment Options

Facilities

Managed By

Local Area

Property Details

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!
  • 1 - 30 of 1,148
    • 3 BR
    • 3 BA
    • Sleeps 8
    6
    Request Booking View Details
    24 hrs Confirmation within 24 hours
      • 6 BR
      • 6 BA
      • Separate Toilets
      • Sleeps 12
      12
      Request Booking View Details
      24 hrs Confirmation within 24 hours
        • 1 BR
        • 1 BA
        • Sleeps 4
        19
        Request Booking View Details
        24 hrs Confirmation within 24 hours
          • 3 BR
          • 3 BA
          • Sleeps 8
          11
          Request Booking View Details
          24 hrs Confirmation within 24 hours
            • 2 BR
            • 2 BA
            • Sleeps 6
            10
            Request Booking View Details
            24 hrs Confirmation within 24 hours
              • 6 BR
              • 5 BA
              • Sleeps 11
              23
              Request Booking View Details
              24 hrs Confirmation within 24 hours
                • 9 BR
                • 7 BA
                • Separate Toilet
                • Sleeps 18
                4
                Request Booking View Details
                24 hrs Confirmation within 24 hours
                  • 1 BR
                  • 1 BA
                  • Sleeps 4
                  24
                  Request Booking View Details
                  24 hrs Confirmation within 24 hours
                    • Studio
                    • 1 BA
                    • Sleeps 4
                    Request Booking View Details
                    24 hrs Confirmation within 24 hours
                      • 4 BR
                      • 2 BA
                      • Separate Toilet
                      • Sleeps 8
                      Request Booking View Details
                      24 hrs Confirmation within 24 hours
                        • 7 BR
                        • 6 BA
                        • Separate Toilet
                        • Sleeps 16
                        7
                        Request Booking View Details
                        24 hrs Confirmation within 24 hours
                          • 6 BR
                          • 6 BA
                          • Separate Toilet
                          • Sleeps 13
                          4
                          Request Booking View Details
                          24 hrs Confirmation within 24 hours
                            • 6 BR
                            • 6 BA
                            • Sleeps 12
                            Request Booking View Details
                            24 hrs Confirmation within 24 hours
                              • 8 BR
                              • 5 BA
                              • Sleeps 14
                              3
                              Request Booking View Details
                              24 hrs Confirmation within 24 hours
                                • 2 BR
                                • 1 BA
                                • Sleeps 5
                                10
                                Request Booking View Details
                                24 hrs Confirmation within 24 hours
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 6
                                  10
                                  Request Booking View Details
                                  24 hrs Confirmation within 24 hours
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 2
                                    4
                                    Request Booking View Details
                                    24 hrs Confirmation within 24 hours
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 4
                                      4
                                      Request Booking View Details
                                      24 hrs Confirmation within 24 hours
                                        • 7 BR
                                        • 6 BA
                                        • Sleeps 13
                                        4
                                        Request Booking View Details
                                        24 hrs Confirmation within 24 hours
                                          • 4 BR
                                          • 4 BA
                                          • Sleeps 10
                                          Request Booking View Details
                                          24 hrs Confirmation within 24 hours
                                            • 1 BR
                                            • 1 BA
                                            • Sleeps 3
                                            Request Booking View Details
                                            24 hrs Confirmation within 24 hours
                                              • 2 BR
                                              • 1 BA
                                              • Sleeps 6
                                              2 Reviews
                                              Request Booking View Details
                                              24 hrs Confirmation within 24 hours
                                                • 5 BR
                                                • 3 BA
                                                • Sleeps 10
                                                Request Booking View Details
                                                24 hrs Confirmation within 24 hours
                                                  • 2 BR
                                                  • 1 BA
                                                  • Sleeps 6
                                                  Request Booking View Details
                                                  24 hrs Confirmation within 24 hours
                                                    £194
                                                    avg/night
                                                    • 4 BR
                                                    • 4 BA
                                                    • Separate Toilet
                                                    • Sleeps 11
                                                    22
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 3
                                                      2 Reviews
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        2 Reviews
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 3
                                                          2 Reviews
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 7
                                                            44
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 5
                                                              10
                                                              • 1 - 30 of 1,148
                                                               

                                                              Recent Reviews

                                                              Perfect

                                                              5 of 5
                                                              Our goal was to stay in the Tuscan countryside and this house did not disappoint. Had everything we needed including a huge fireplace that we utilized daily. Close to town but out far enough to get gorgeous views of the countryside. Sunrises were breathtaking as well. We will definetly stay here again on our next trip back to Imprunetta. If you are looking to stay in the countryside in an authentic Italian house, this is the place.
                                                              • Review Submitted: 02-Feb-2016
                                                              • Date of Stay: Oct 2015

                                                              Idyllic Italian haven!

                                                              5 of 5
                                                              San Casciano Val Di Pesa epitomizes all that there is to love and savor about Italian life. Each morning my four year old would dramatically throw open our wooden shutters, shouting out Bon Journo to the cockerel, hens and cuckoo birds that inhabited our stunning gardens. Our 280 degree view was framed by the Florentine mountains in the back ground to the rolling valley of vineyards and olive groves in the foreground. As we cooked, chatted and played with our children in the kitchen, this view peered in at us, catching our breath each time. The villa is sensitively and immaculately preserved, the pictures show the interior as it is. The photos of the gardens however do not indicate how vast that space is. It is beautifully planted, with real privacy offered from each veranda. You also are free to wander throughout the proprietor's estate. Walks through the vineyards and forests provided my four year old with a great adventures. I also went for my morning run around the estate - a 4 km circuit, providing stunning views of the area and much safer than running on the local, narrow roads. Maurizio and Antonio, were very gracious hosts. Always courteous and readily available to resolve any queries we had. We were also treated to a tour of their cellar and a bottle of their exquisite Chianti wine. San Casciano, only 8 km away, (Mercatale - 4 km away, fine for grocery shopping and had a charming playground) was a real find. We went there nearly every evening, and we felt like we were the only tourists there. It's an affluent, effortlessly elegant town, with a sufficient array of restaurants, cafes and shops to create an ambient atmosphere. They playground had the most incredible view of a river valley, in the cool of the evening all the locals loved to amble along its edge; a perfect spot for people watching. My only reservation was the road leading up to the villa, it was eroded quite severely in parts, making driving a hired car quite a precarious experience. Lastly San Casciano, is the perfect spot for exploring Chianti. We were 30 mins from Florence, 40 from Sienna. Two other towns I must recommend are San Gimignano, home to the worlds first skyscraper and apparently the best icecream too. I loved it for its piazza that contained the best set of steps, far superior to the Steps of Rome, much more atmospheric. The other town is Panzano, a hill top town with a famously cultured butcher. Incredible views while there and enroute.
                                                              • Review Submitted: 18-Jul-2015
                                                              • Date of Stay: Jun 2015

                                                              Beautiful & Relaxing Stay

                                                              5 of 5
                                                              My husband and I visited this property the last week of July 2009 and stayed for one week. Where do I begin...The apartment was perfect! It contained everything that you would ever need for your stay including laundry facilities and a dishwasher. We shopped in the local market and prepared most of our meals. We typically ate out once per day depending on where our travels took us. This property is located in perfect proximity for day trips to Pisa, Florence and Siena (which we did). We did a day trip every other day and just hung back at the little villages nearby on the off days. Rita offers cooking classes at an extremely inexpensive price and we used the vegetables and herbs fresh from her garden. And let me assure you...the meal was delicious. The view from the back garden is magnificent. We ate overlooking the rolling hillside of vineyards and olive groves. The village is a 2 minute drive and could be walked (it’s just a bit hilly). Nice village with an internet cafe/coffee shop if you didn’t bring your computer. Rosita, Rita and Faustus not only welcomed us into their home, but also into their hearts. We flew into Rome on a Sunday morning where we picked up our rental car and drove straight to the castle for our first week (of a 2 week trip). Of course, nothing is open on Sundays so Rita prepared a wonderful dinner for us and we enjoyed it in the back garden with a bottle of wine from Faustus' vineyard. We also chose the option for breakfast the next morning as we had yet to get groceries. When we left, we went to Venice for 3 nights where we rented an apartment that seemed so cold to us after having stayed at Castello di Colognole. If they had not had our apartment already rented for the next week. I would have much rather stayed there longer. They have two dogs who are very playful and well behaved. As we lost our puppy early July, we felt so blessed to be around Bacco and Jemma. There is no air conditioning, however, there are fans and we did not have any trouble sleeping. They do have misquittos but so do we here in Canada. Rosita speaks english with minimal difficulty. Rita is learning and we really didn't have any trouble communicating. If you are looking to enrich your life by experiencing the authenic life in Tuscany, this place is a must! It was truly like a second honeymoon for us! We will definitely return...but next time, for a longer period of time. Corrinne & Stephen
                                                              • Review Submitted: 16-Nov-2009
                                                              • Date of Stay: Jul 2009