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Holidaymakers searching for holiday rentals in San Casciano in Val di Pesa also enquired about villas in Cortona, apartments in Greve in Chianti and apartments in Lucca

Make a holiday rental property or villa in San Casciano in Val di Pesa, Italy your home away from home

Deep in the hills of the Chianti region of Tuscany is the hilltop town of San Casciano in Val di Pesa. Inhabited since the 7th century BC, San Casciano Val di Pesa has an ancient feel, with buildings and monuments of many styles mixing perfectly throughout the village in amazing harmony. Holiday rental accommodation in San Casciano in Val di Pesa is a fantastic option for those who wish to sample true Tuscan life in the peace of the stunning Chianti landscape, yet with all the major attractions of Tuscany at your disposal.

Things to do on holiday in San Casciano in Val di Pesa, Italy

There are some excellent historical attractions in the area worth visiting. Sections of the 14th century defensive walls which once protected San Casciano in Val di Pesa can still be seen, and there are some wonderful works of art adorning the interior of the Collegiata, the Church of the Miserocordia and the Compagnia del Suffragio which are certainly worth investigating if you have any interest in art. The huge 14th century castle, the Castello di Bibbione dominates the landscape, and can be seen from almost anywhere in the village. The Sacred Arts Museum is located in the Church of Santa Maria del Gesu, displaying many important works.

Walking the streets of San Casciano in Val di Pesa is a delight. The wide boulevards are filled with delightful little boutiques, sunny pavement cafes and restaurants pouring mouth watering smells into the air. Sitting in the sun outside a café and watching the world go by is a timeless delight in San Casciano Val di Pesa, with beautiful terracotta villas and ancient stone defences providing a backdrop that even seasoned travellers will be affected by.

The Pesa Valley is a great place to walk too. The blossoming groves and colourful meadows of the Pesa Valley make it a great place to walk, and if you get up onto any of the ridge ways which dissect the area, you can discover some magnificent viewpoints over the Tuscan countryside.

Places to visit on holiday in San Casciano in Val di Pesa, Italy

The highly popular Renaissance cities of Florence and Siena are both within easy reach of any self catering holiday property in San Casciano in Val di Pesa. The birthplace of the Renaissance movement, Florence is a magnificent place to visit, and one you should really see at least once during your lifetime. The famous city centre has been declared a UNESCO World Heritage Site due to the amazing concentration of important works, and although it really is an amazing place to visit, being able to escape the crowds in the evenings is a true delight.

Weather in San Casciano in Val di Pesa, Italy

Summers in San Casciano in Val di Pesa are blissfully warm, with temperatures averaging around 30°C. In the winter months, temperatures average 8°C during January and February, with daily conditions often perfect for sightseeing or walking through the vineyards of the Tuscan countryside.

Travel to San Casciano in Val di Pesa, Italy

A holiday rental villa in San Casciano Val di Pesa is just 16km from Florence International Airport (FLR). Luckily for those of us visiting from the UK, Meridiana Airlines run a service from London Gatwick (LGW) straight to Florence. There are many transfer options, with car hire companies, bus services and pre-paid taxis.

  • Showing 1-50 of 300+
Additional service fee may apply.
    Wonderful! 4.9/5
    (38 reviews)
    avg/night
    • 2 BR
    • 2 BA
    • Sleeps 6
    Multiple rentals Apartment #632967a
    38
    Viewed 61 times in the last 48 hours
      • 1 BR
      • 1 BA
      • Sleeps 3
      Multiple rentals Apartment #6622282
      4
      Viewed 25 times in the last 48 hours
        Wonderful! 4.9/5
        (14 reviews)
        avg/night
        • 4 BR
        • 3 BA
        • Sleeps 10
        House #6042176
        14
        Viewed 101 times in the last 48 hours
          Exceptional! 5.0/5
          (39 reviews)
          avg/night
          • 2 BR
          • 2 BA
          • Sleeps 6
          Multiple rentals Chateau / Country House #6153067
          39
          Viewed 32 times in the last 48 hours
            Excellent! 4.7/5
            (11 reviews)
            avg/night
            • 1 BR
            • 1 BA
            • Sleeps 2
            Multiple rentals Studio #632967a
            11
            Viewed 5 times in the last 48 hours
              Wonderful! 4.9/5
              (30 reviews)
              avg/night
              • 2 BR
              • 2 BA
              • Sleeps 5
              Multiple rentals Chateau / Country House #6153067
              30
              Viewed 37 times in the last 48 hours
                Exceptional! 5.0/5
                (43 reviews)
                avg/night
                • 2 BR
                • 1 BA
                • Sleeps 4
                Multiple rentals Apartment #6055204
                43
                Viewed 56 times in the last 48 hours
                  Excellent! 4.7/5
                  (10 reviews)
                  avg/night
                  • 3 BR
                  • 3 BA
                  • Sleeps 8
                  Villa #342134vb
                  10
                  Viewed 47 times in the last 48 hours
                    Exceptional! 5.0/5
                    (19 reviews)
                    avg/night
                    • 3 BR
                    • 2 BA
                    • Sleeps 8
                    Villa #467172vb
                    19
                    Viewed 53 times in the last 48 hours
                      Exceptional! 5.0/5
                      (5 reviews)
                      avg/night
                      • 8 BR
                      • 8 BA
                      • Separate Toilets
                      • Sleeps 16
                      Villa #804869vb
                      5
                      Viewed 63 times in the last 48 hours
                        Excellent! 4.7/5
                        (7 reviews)
                        avg/night
                        • 2 BR
                        • 2 BA
                        • Sleeps 5
                        Barn #1697270
                        7
                        Viewed 23 times in the last 48 hours
                          Wonderful! 4.9/5
                          (29 reviews)
                          avg/night
                          • 1 BR
                          • 1 BA
                          • Sleeps 4
                          Multiple rentals Farmhouse #450158
                          29
                          Viewed 33 times in the last 48 hours
                            Exceptional! 5.0/5
                            (38 reviews)
                            avg/night
                            • 2 BR
                            • 1 BA
                            • Sleeps 4
                            Multiple rentals Apartment #6055204
                            38
                            Viewed 29 times in the last 48 hours
                              • 2 BR
                              • 1 BA
                              • Sleeps 6
                              Multiple rentals Apartment #6622282
                              4
                              Viewed 94 times in the last 48 hours
                                Wonderful! 4.8/5
                                (19 reviews)
                                avg/night
                                • 3 BR
                                • 3 BA
                                • Sleeps 6
                                Apartment #6350241
                                19
                                Viewed 85 times in the last 48 hours
                                  • 4 BR
                                  • 4 BA
                                  • Sleeps 10
                                  Multiple rentals Villa #6622282
                                  2
                                  Viewed 36 times in the last 48 hours
                                    • Studio
                                    • 1 BA
                                    • Sleeps 4
                                    Multiple rentals Apartment #450158
                                    Viewed 16 times in the last 48 hours
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 8
                                      Villa #1834327
                                      22
                                      Viewed 42 times in the last 48 hours
                                        avg/night
                                        • 5 BR
                                        • 2 BA
                                        • Sleeps 6
                                        House #399314vb
                                        2
                                        Viewed 21 times in the last 48 hours
                                          Wonderful! 4.8/5
                                          (30 reviews)
                                          avg/night
                                          • 4 BR
                                          • 3 BA
                                          • Sleeps 11
                                          Multiple rentals Chateau / Country House #6255150
                                          30
                                          Viewed 20 times in the last 48 hours
                                            Wonderful! 4.8/5
                                            (37 reviews)
                                            avg/night
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 3
                                            Apartment #72021
                                            37
                                            Viewed 7 times in the last 48 hours
                                              Excellent! 4.7/5
                                              (6 reviews)
                                              avg/night
                                              • 2 BR
                                              • 3 BA
                                              • Separate Toilets
                                              • Sleeps 11
                                              Guest House #682691a
                                              6
                                              Viewed 40 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (33 reviews)
                                                avg/night
                                                • 1 BR
                                                • 1 BA
                                                • Sleeps 4
                                                Chateau / Country House #6042181
                                                33
                                                Viewed 18 times in the last 48 hours
                                                  Exceptional! 5.0/5
                                                  (15 reviews)
                                                  avg/night
                                                  • 2 BR
                                                  • 1 BA
                                                  • Sleeps 7
                                                  Multiple rentals Chateau / Country House #6255150
                                                  15
                                                  Viewed 8 times in the last 48 hours
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 3
                                                    Apartment #587384vb
                                                    3
                                                    Viewed 32 times in the last 48 hours
                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 4
                                                      Apartment #20210
                                                      17
                                                        • 4 BR
                                                        • 3 BA
                                                        • Sleeps 12
                                                        Villa #1619355
                                                        7
                                                          Exceptional! 5.0/5
                                                          (6 reviews)
                                                          avg/night
                                                          • 5 BR
                                                          • 3 BA
                                                          • Separate Toilet
                                                          • Sleeps 10
                                                          Villa #6318488
                                                          6
                                                          Viewed 7 times in the last 48 hours
                                                            Exceptional! 5.0/5
                                                            (5 reviews)
                                                            avg/night
                                                            • 1 BR
                                                            • 1 BA
                                                            • Separate Toilet
                                                            • Sleeps 2
                                                            Studio #6450649
                                                            5
                                                              Excellent! 4.7/5
                                                              (15 reviews)
                                                              avg/night
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 2
                                                              Cottage #6621133
                                                              15
                                                              Viewed 9 times in the last 48 hours
                                                                • 5 BR
                                                                • 6 BA
                                                                • Sleeps 12
                                                                Villa #6870184
                                                                3
                                                                Viewed 5 times in the last 48 hours
                                                                  Wonderful! 4.8/5
                                                                  (5 reviews)
                                                                  avg/night
                                                                  • 3 BR
                                                                  • 1 BA
                                                                  • Sleeps 6
                                                                  Apartment #3466748
                                                                  5
                                                                  Viewed 7 times in the last 48 hours
                                                                    Wonderful! 4.9/5
                                                                    (15 reviews)
                                                                    avg/night
                                                                    • 6 BR
                                                                    • 5 BA
                                                                    • Separate Toilet
                                                                    • Sleeps 12
                                                                    Villa #1192463
                                                                    15
                                                                    Viewed 18 times in the last 48 hours
                                                                      Exceptional! 5.0/5
                                                                      (5 reviews)
                                                                      avg/night
                                                                      • Studio
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      House #1749773
                                                                      5
                                                                      Viewed 9 times in the last 48 hours
                                                                        Exceptional! 5.0/5
                                                                        (5 reviews)
                                                                        avg/night
                                                                        • 7 BR
                                                                        • 7 BA
                                                                        • Sleeps 14
                                                                        Villa #1336481
                                                                        5
                                                                        Viewed 12 times in the last 48 hours
                                                                          • 8 BR
                                                                          • 9 BA
                                                                          • Sleeps 17
                                                                          Villa #6908175
                                                                          2
                                                                          Viewed 25 times in the last 48 hours
                                                                            Exceptional! 5.0/5
                                                                            (16 reviews)
                                                                            avg/night
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Sleeps 7
                                                                            Villa #36918vb
                                                                            16
                                                                            Viewed 7 times in the last 48 hours
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 8
                                                                              Barn #6273803
                                                                              7
                                                                                • 4 BR
                                                                                • 3 BA
                                                                                • Sleeps 8
                                                                                Apartment #1084998
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 3 BA
                                                                                  • Sleeps 6
                                                                                  Cottage #1975918
                                                                                  Viewed 5 times in the last 48 hours
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 6
                                                                                    Apartment #1085544
                                                                                      • 5 BR
                                                                                      • 4 BA
                                                                                      • Sleeps 10
                                                                                      Villa #826215
                                                                                      2
                                                                                      Viewed 17 times in the last 48 hours
                                                                                        Exceptional! 5.0/5
                                                                                        (20 reviews)
                                                                                        avg/night
                                                                                        • 6 BR
                                                                                        • 4 BA
                                                                                        • Sleeps 12
                                                                                        Villa #6124320
                                                                                        20
                                                                                        Viewed 6 times in the last 48 hours
                                                                                          avg/night
                                                                                          • 5 BR
                                                                                          • 4 BA
                                                                                          • Separate Toilet
                                                                                          • Sleeps 11
                                                                                          Multiple rentals Chateau / Country House #6369421
                                                                                          4
                                                                                          Viewed 11 times in the last 48 hours
                                                                                            Excellent! 4.4/5
                                                                                            (7 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Separate Toilet
                                                                                            • Sleeps 4
                                                                                            Multiple rentals Farmhouse #6369421
                                                                                            7
                                                                                            Viewed 17 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (9 reviews)
                                                                                              avg/night
                                                                                              • 3 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 8
                                                                                              Villa #1658572
                                                                                              9
                                                                                              Viewed 14 times in the last 48 hours
                                                                                                Exceptional! 5.0/5
                                                                                                (25 reviews)
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 5
                                                                                                Chateau / Country House #6023842
                                                                                                25
                                                                                                Viewed 6 times in the last 48 hours
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 2
                                                                                                  Apartment #2066493
                                                                                                  2
                                                                                                    avg/night
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 4
                                                                                                    Apartment #577218a
                                                                                                    3
                                                                                                    Viewed 9 times in the last 48 hours
                                                                                                    • 1 - 50 of 300+

                                                                                                    San Casciano in Val di Pesa Holiday Apartments & Villas (300+)

                                                                                                     

                                                                                                    Recent Reviews

                                                                                                    Charming and peaceful

                                                                                                    5 of 5
                                                                                                    Charming, pretty apartment with enchanting views. Peaceful and quiet, no road noise! Very knowledgeable and informative host. We recommend it!!
                                                                                                    • Review Submitted: 23-Aug-2016
                                                                                                    • Date of Stay: Aug 2016

                                                                                                    Perfect stay for a family with children

                                                                                                    5 of 5
                                                                                                    Very good place with nice views. Good facilities and nice pool area. Everything is clean. Good location near Firenze. Alessandra is very helpful and friendly person. I would recommend this place to my friends.
                                                                                                    • Review Submitted: 05-Aug-2016
                                                                                                    • Date of Stay: Jul 2016

                                                                                                    Villa Gentile is a lovely rural rustic retreat, we loved it and will return

                                                                                                    5 of 5
                                                                                                    Villa Gentile is a lovely rural rustic retreat, we loved it and will return. The building is over 200 years old and has retained its character and charm and is located within the vineyard and olive trees. The indoor table tennis great for a few minutes cool off from the heat or evening entertainment. Swimming in a warm pool in the early morning and late evening a daily 'treat'. We loved it, lovely location and wonderfully welcoming, we wouldn't want to see anything changed. The owners are very welcoming and friendly. We have had a great service from Summer In Italy and will not hesitate to book again. You advised fully of the nature of the property and we were well prepared for its rustic style, it more than lived up to our expectations. We loved it and have already recommended it to others.
                                                                                                    • Review Submitted: 24-Oct-2015
                                                                                                    • Date of Stay: Aug 2015