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.
Verified Review icon 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 pet-dog svg-multiunit

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.

  • Showing 1-50 of 300+
Additional service fee may apply.
  View Map Map
    • 2 BR
    • 2 BA
    • Sleeps 4
    Multiple rentals Villa #812782
    1
      Exceptional! 5.0/5
      (7 reviews)
      avg/night
      • 4 BR
      • 4 BA
      • Sleeps 8
      Multiple rentals Villa #812782
      7
      Viewed 7 times in the last 48 hours
        Exceptional! 5.0/5
        (16 reviews)
        avg/night
        • 2 BR
        • 2 BA
        • Sleeps 4
        Apartment #486189vb
        16
        Viewed 9 times in the last 48 hours
          Excellent! 4.4/5
          (16 reviews)
          avg/night
          • 2 BR
          • 2 BA
          • Sleeps 5
          Apartment #167744vb
          16
          Viewed 8 times in the last 48 hours
            • 1 BR
            • 1 BA
            • Sleeps 2
            House #2486857
            1
              • 1 BR
              • 1 BA
              • Sleeps 2
              Apartment #6710973
                • 2 BR
                • 1 BA
                • Sleeps 5
                Apartment #6816248
                  • 8 BR
                  • 8 BA
                  • Sleeps 12
                  Villa #6556491
                    • 4 BR
                    • 4 BA
                    • Separate Toilets
                    • Sleeps 10
                    Villa #4315688
                      • 8 BR
                      • 8 BA
                      • Separate Toilet
                      • Sleeps 19
                      Villa #6548383
                        • 4 BR
                        • 4 BA
                        • Sleeps 8
                        Villa #1810426
                          • 8 BR
                          • 1 BA
                          • Sleeps 19
                          Villa #1810676
                            • 7 BR
                            • 5 BA
                            • Sleeps 15
                            Villa #6489127
                              • 6 BR
                              • 6 BA
                              • Sleeps 10
                              Villa #6487445
                                • 8 BR
                                • 8 BA
                                • Sleeps 14
                                Villa #1799629
                                  • 6 BR
                                  • 6 BA
                                  • Sleeps 11
                                  Villa #1810198
                                    • 6 BR
                                    • 6 BA
                                    • Sleeps 14
                                    Villa #1799610
                                      • 5 BR
                                      • 3 BA
                                      • Sleeps 13
                                      Villa #1810450
                                        • 5 BR
                                        • 6 BA
                                        • Sleeps 10
                                        Villa #1810197
                                          • 2 BR
                                          • 2 BA
                                          • Sleeps 4
                                          Apartment #1810585
                                            • 2 BR
                                            • 2 BA
                                            • Sleeps 4
                                            Apartment #1810586
                                              • 1 BR
                                              • 2 BA
                                              • Sleeps 4
                                              House #2486839
                                                • 1 BR
                                                • 1 BA
                                                • Sleeps 2
                                                House #2486856
                                                  • 3 BR
                                                  • 4 BA
                                                  • Sleeps 8
                                                  House #2488973
                                                    avg/night
                                                    • 4 BR
                                                    • 5 BA
                                                    • Sleeps 9
                                                    House #6667331
                                                    Viewed 13 times in the last 48 hours
                                                      Exceptional! 5.0/5
                                                      (8 reviews)
                                                      avg/night
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 2
                                                      Chateau / Country House #6115214
                                                      8
                                                      Viewed 80 times in the last 48 hours
                                                        Exceptional! 5.0/5
                                                        (26 reviews)
                                                        avg/night
                                                        • 4 BR
                                                        • 3 BA
                                                        • Sleeps 10
                                                        Villa #6415307
                                                        26
                                                        Viewed 71 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (75 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          Chateau / Country House #436049vb
                                                          75
                                                          Viewed 43 times in the last 48 hours
                                                            Exceptional! 5.0/5
                                                            (11 reviews)
                                                            avg/night
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            Apartment #757059vb
                                                            11
                                                            Viewed 6 times in the last 48 hours
                                                              Wonderful! 4.9/5
                                                              (35 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 3 BA
                                                              • Sleeps 5
                                                              Villa #62257
                                                              35
                                                              Viewed 43 times in the last 48 hours
                                                                Exceptional! 5.0/5
                                                                (9 reviews)
                                                                avg/night
                                                                • 5 BR
                                                                • 5 BA
                                                                • Sleeps 12
                                                                Villa #1812215
                                                                9
                                                                Viewed 16 times in the last 48 hours
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 3
                                                                  Apartment #1996686
                                                                  2
                                                                  Viewed 20 times in the last 48 hours
                                                                    Exceptional! 5.0/5
                                                                    (6 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    Apartment #479613vb
                                                                    6
                                                                    Viewed 58 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (42 reviews)
                                                                      avg/night
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 3
                                                                      Apartment #50681
                                                                      42
                                                                      Viewed 15 times in the last 48 hours
                                                                        Exceptional! 5.0/5
                                                                        (13 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 6
                                                                        Cottage #1760582
                                                                        13
                                                                        Viewed 26 times in the last 48 hours
                                                                          Exceptional! 5.0/5
                                                                          (14 reviews)
                                                                          avg/night
                                                                          • 3 BR
                                                                          • 3 BA
                                                                          • Sleeps 10
                                                                          Farmhouse #3749715
                                                                          14
                                                                          Viewed 16 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
                                                                            Viewed 10 times in the last 48 hours
                                                                              Exceptional! 5.0/5
                                                                              (25 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              Apartment #3877682
                                                                              25
                                                                              Viewed 11 times in the last 48 hours
                                                                                • 6 BR
                                                                                • 3 BA
                                                                                • Sleeps 12
                                                                                Villa #1893413
                                                                                3
                                                                                Viewed 17 times in the last 48 hours
                                                                                  Wonderful! 4.9/5
                                                                                  (21 reviews)
                                                                                  avg/night
                                                                                  • 4 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 10
                                                                                  House #376809vb
                                                                                  21
                                                                                  Viewed 35 times in the last 48 hours
                                                                                    Exceptional! 5.0/5
                                                                                    (5 reviews)
                                                                                    avg/night
                                                                                    • 7 BR
                                                                                    • 5 BA
                                                                                    • Sleeps 14
                                                                                    Villa #6804820
                                                                                    5
                                                                                    Viewed 48 times in the last 48 hours
                                                                                      Exceptional! 5.0/5
                                                                                      (14 reviews)
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 6
                                                                                      Apartment #1017638
                                                                                      14
                                                                                      Viewed 7 times in the last 48 hours
                                                                                        Wonderful! 4.9/5
                                                                                        (50 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 5
                                                                                        Apartment #6176004
                                                                                        50
                                                                                        Viewed 8 times in the last 48 hours
                                                                                          Exceptional! 5.0/5
                                                                                          (11 reviews)
                                                                                          avg/night
                                                                                          • 3 BR
                                                                                          • 4 BA
                                                                                          • Sleeps 7
                                                                                          Villa #6240427
                                                                                          11
                                                                                          Viewed 13 times in the last 48 hours
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 3
                                                                                            Multiple rentals Apartment #1105349
                                                                                            3
                                                                                              Wonderful! 4.8/5
                                                                                              (8 reviews)
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 7
                                                                                              Multiple rentals Chateau / Country House #1105349
                                                                                              8
                                                                                              Viewed 10 times in the last 48 hours
                                                                                                Exceptional! 5.0/5
                                                                                                (15 reviews)
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 4 BA
                                                                                                • Sleeps 9
                                                                                                Villa #3718707
                                                                                                15
                                                                                                Viewed 42 times in the last 48 hours
                                                                                                  Exceptional! 5.0/5
                                                                                                  (9 reviews)
                                                                                                  avg/night
                                                                                                  • 7 BR
                                                                                                  • 6 BA
                                                                                                  • Sleeps 14
                                                                                                  Villa #1694354
                                                                                                  9
                                                                                                  Viewed 12 times in the last 48 hours
                                                                                                  • 1 - 50 of 300+
                                                                                                   

                                                                                                  Recent Reviews

                                                                                                  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

                                                                                                  Villa l' Anitca Posta was magnificent!

                                                                                                  5 of 5
                                                                                                  Five friends and I stayed at this wonderful property and we all enjoyed it very much. Belinda was an excellent and considerate host. The property is meticulously maintained with beautiful furnishings, large rooms, a chef's kitchen, wonderful scenery and outdoor areas. It exceeded all of our expectations, even though the photos and descriptions were clear and accurate. We all agreed that we would be very happy to return for a stay sometime in the future.
                                                                                                  • Review Submitted: 19-Aug-2016
                                                                                                  • Date of Stay: Apr 2016