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Holidaymakers searching for holiday rentals in Pienza also enquired about apartments in Montepulciano, villas in Cortona and apartments in Lucca

Make a holiday rental home or villa in Pienza, Italy your home away from home

Pienza is a town located in the heart of Tuscany, Italy. It is known as the “Touchstone of Renaissance Urbanism” and has been a UNESCO-declared World Heritage Site since 1996.

Due to its location deep in the heart of the Val d’Orcia, the surrounding landscape is untouched, and houses some of the region’s most beautiful landscape. Pienza is slightly off the usual tourist route, so allows visitors to get off the beaten track and experience a model of real Tuscan life.

Popular accommodations include renovated farm houses and other rental accommodations. Why not enjoy a holiday rental in Pienza, Tuscany for your next vacation?

Things to do in Pienza, Italy

The town’s central piazza is defined by four buildings. One the west side is the Palazzo Piccolomini, known for its beautiful gardens, which offer spectacular views of the surrounding Val d’Orcia countryside. The piazza is dominated by the Duomo, one of the first cathedrals to be designed during the Renaissance. The Piccolomini and Borgia Palaces and also are a testimony to architect Bernardo Rosselino. His extraordinary vision has made the town’s historic centre one of the finest in the world. Many other 14th and 15th Century buildings are dotted around the town, making it an enjoyable sightseeing opportunity.

A popular method of enjoying the surrounding countryside is to hire a bike, allowing you to cover more distance than on foot (though trekking in the hills is also popular). By hiring a bike you will be able to visit several of the regions farms and wineries for tasting sessions, though don’t overdo it if you have to cycle back! Some of these also offer food, making a winery tour a day-long excursion. What could be better than soaking up the Tuscan sun with a glass of locally-made wine?

Places to visit on holiday in Pienza, Italy

Whilst holidaying in Pienza you may wish to get out of the countryside and into the bigger cities. Indeed, as you will likely be flying into either Rome or Pisa, you are presented with a great opportunity to explore one of these historic cities and world-famous monuments.

If you hired a car to get to Pienza, you could also use this to see more of the Val d’Orcia region, which extends from the hills south of Siena to Monte Amiata. Recommended destinations include Radicofani and Montalcino

Weather in Pienza, Italy

The climate of Tuscany has different characteristics depending on the area, and Pienza is no different. The summer months reach an average of 28C, making it more bearable than some other Tuscan regions. Autumn and Spring are also pleasant times to visit, and the winters are mild, so in short, any time of year is great for a holiday rental in Pienza.

Flights to Pienza, Italy

There are two choices of Airport in order to reach Pienza, - Rome (FCO) and Pisa (PSA). Several UK airlines run regular flights to these destinations. You can then take public transport from there to Pienza, though car hire is a lot easier as buses do not run that frequently.

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  • 1 - 50 of 300+
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    • 4 BR
    • 4 BA
    • Sleeps 10
    Villa #1455695
    Viewed 18 times in the last 48 hours
      Exceptional! 5.0/5
      (9 reviews)
      avg/night
      • 5 BR
      • 5 BA
      • Sleeps 12
      Villa #1812215
      9
      Viewed 15 times in the last 48 hours
        Exceptional! 5.0/5
        (70 reviews)
        avg/night
        • 3 BR
        • 2 BA
        • Sleeps 6
        Chateau / Country House #436049vb
        70
        Viewed 6 times in the last 48 hours
          Wonderful! 4.9/5
          (8 reviews)
          avg/night
          • 1 BR
          • 1 BA
          • Sleeps 3
          Apartment #515580
          8
          Viewed 7 times in the last 48 hours
            • 2 BR
            • 2 BA
            • Sleeps 4
            Multiple rentals Apartment #7160
            9
              Exceptional! 5.0/5
              (11 reviews)
              avg/night
              • 3 BR
              • 4 BA
              • Sleeps 7
              Villa #6240427
              11
              Viewed 9 times in the last 48 hours
                • 2 BR
                • 1 BA
                • Separate Toilet
                • Sleeps 6
                Multiple rentals House #447800
                1
                  Excellent! 4.3/5
                  (7 reviews)
                  avg/night
                  • 2 BR
                  • 1 BA
                  • Separate Toilet
                  • Sleeps 6
                  Multiple rentals House #411866
                  7
                  Viewed 55 times in the last 48 hours
                    • 4 BR
                    • 4 BA
                    • Separate Toilet
                    • Sleeps 10
                    Villa #1674525
                    10
                      • 3 BR
                      • 3 BA
                      • Sleeps 10
                      Multiple rentals Villa #447800
                      1
                        • 1 BR
                        • 1 BA
                        • Sleeps 3
                        Multiple rentals Apartment #7160
                        1
                          Exceptional! 5.0/5
                          (5 reviews)
                          avg/night
                          • 3 BR
                          • 3 BA
                          • Sleeps 8
                          Multiple rentals Villa #411866
                          5
                          Viewed 8 times in the last 48 hours
                            • 4 BR
                            • 4 BA
                            • Sleeps 9
                            Villa #1633045
                            1
                              • 6 BR
                              • 5 BA
                              • Separate Toilet
                              • Sleeps 12
                              Villa #1150695
                                • 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
                                          • 2 BR
                                          • 2 BA
                                          • Sleeps 4
                                          Villa #1544793
                                            • 5 BR
                                            • 7 BA
                                            • Sleeps 10
                                            Villa #1908361
                                              Exceptional! 5.0/5
                                              (19 reviews)
                                              avg/night
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 6
                                              Apartment #615969vb
                                              19
                                              Viewed 5 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (42 reviews)
                                                avg/night
                                                • 1 BR
                                                • 1 BA
                                                • Sleeps 3
                                                Apartment #50681
                                                42
                                                Viewed 19 times in the last 48 hours
                                                  avg/night
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 3
                                                  Apartment #1770926
                                                  4
                                                  Viewed 7 times in the last 48 hours
                                                    Wonderful! 4.9/5
                                                    (47 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 7
                                                    Apartment #6066867
                                                    47
                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 5
                                                      Apartment #6176004
                                                      50
                                                        • 7 BR
                                                        • 5 BA
                                                        • Sleeps 16
                                                        Multiple rentals Villa #6347473
                                                        2
                                                        Viewed 7 times in the last 48 hours
                                                          Exceptional! 5.0/5
                                                          (13 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 5
                                                          Apartment #620994vb
                                                          13
                                                          Viewed 5 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (35 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 3 BA
                                                            • Sleeps 5
                                                            Villa #62257
                                                            35
                                                            Viewed 11 times in the last 48 hours
                                                              Exceptional! 5.0/5
                                                              (32 reviews)
                                                              avg/night
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 2
                                                              Apartment #204437vb
                                                              32
                                                              Viewed 10 times in the last 48 hours
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                Villa #1506754
                                                                1
                                                                  Exceptional! 5.0/5
                                                                  (8 reviews)
                                                                  avg/night
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 2
                                                                  Chateau / Country House #6115214
                                                                  8
                                                                  Viewed 7 times in the last 48 hours
                                                                    Exceptional! 5.0/5
                                                                    (11 reviews)
                                                                    avg/night
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 2
                                                                    Apartment #3967191
                                                                    11
                                                                    Viewed 9 times in the last 48 hours
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • Sleeps 5
                                                                      Apartment #402597
                                                                      9
                                                                        • 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 13 times in the last 48 hours
                                                                            • 8 BR
                                                                            • 7 BA
                                                                            • Sleeps 18
                                                                            Villa #442376
                                                                            1
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              Multiple rentals House #8038414
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Separate Toilet
                                                                                • Sleeps 8
                                                                                Multiple rentals House #8038414
                                                                                  • 3 BR
                                                                                  • 3 BA
                                                                                  • Sleeps 8
                                                                                  Multiple rentals Villa #8038414
                                                                                  1
                                                                                    • 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
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 4
                                                                                        Multiple rentals Villa #812782
                                                                                        1
                                                                                          • 4 BR
                                                                                          • 4 BA
                                                                                          • Sleeps 8
                                                                                          Multiple rentals Villa #812782
                                                                                          7
                                                                                            Exceptional! 5.0/5
                                                                                            (26 reviews)
                                                                                            avg/night
                                                                                            • 4 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 10
                                                                                            Villa #6415307
                                                                                            26
                                                                                            Viewed 27 times in the last 48 hours
                                                                                            • 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

                                                                                            Comfortable and quiet property in a super location!

                                                                                            5 of 5
                                                                                            This property is ideally situated for exploring some beautiful Tuscan towns and viewing the beautiful scenery. Easy to get to from the motorway. Comfortable villa with everything you need. The hosts were wonderful, helpful and informative at every point. There's plenty to do in the area without having to travel miles to get there. If you want a quiet day at home then the pool area is comfortable and private. We would certainly return and book this villa again.
                                                                                            • Review Submitted: 29-Sep-2016
                                                                                            • Date of Stay: Sep 2016

                                                                                            Beautiful, spacious, air conditioned Tuscan villa

                                                                                            5 of 5
                                                                                            The property was as beautiful as the pictures and even more spacious inside -- the main house is very large and the other two cottages are very nice as well (one more kid oriented, the other more luxurious and great for a couple) the bedrooms and bathrooms are all very beautifully finished with a luxurious feel and lots of storage space and other extras. The kitchen and common areas have everything you would want in a holiday home, the pool was warm and sunny with a great view and a great size for either swimming laps or kids playing. The grounds were big enough for the kids (aged 6-8) to run around and play. Service was great as was the night with the chef. The air conditioning worked well and a great benefit. We had only 2 families (could easily fit more) but chose to pay the supplement for one extra bed as we wanted the 3 kids all together in one room /cottage and that was the only way to get that arrangement. The perfect place for a holiday/vacation in Italy.
                                                                                            • Review Submitted: 11-Sep-2016
                                                                                            • Date of Stay: Aug 2016