Apartments in San Casciano in Val di Pesa and Villas – Holiday Lettings - Holiday Rentals San Casciano in Val di Pesa

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9,074 Holiday homes

(4) Excellent 

    45

    Holiday villa rental

    Province of Florence / San Casciano in Val di Pesa

    8 16 1 night min

    • 8 bedrooms
    • sleeps 16
    • 1 night min
    • Nearest beach 90 km
    • Swimming pool
    • Child friendly

    from £1,144 / night

    £8,004 - £10,467 / week

    Book View

    from £1,144 / night

    (2) Excellent 

      21

      Apartment rental in Campoli in Chianti with shared pool

      San Casciano in Val di Pesa / Campoli in Chianti

      2 6 3 nights min

      • 2 bedrooms
      • sleeps 6
      • 3 nights min
      • Swimming pool
      • Child friendly
      • Air conditioning

      from £126 / night

      £756 / week

      Book View

      from £126 / night

        17

        Campoli in Chianti holiday apartment rental

        San Casciano in Val di Pesa / Campoli in Chianti

        1 3 3 nights min

        • 1 bedroom
        • sleeps 3
        • 3 nights min
        • Swimming pool
        • Child friendly
        • Air conditioning

        from £91 / night

        £504 / week

        Book View

        from £91 / night

        (3) Excellent 

          15

          San Casciano in Val di Pesa holiday villa rental

          Province of Florence / San Casciano in Val di Pesa

          5 11 7 nights min

          • 5 bedrooms
          • sleeps 11
          • 7 nights min
          • Swimming pool
          • Child friendly
          • Private garden

          from £576 / night

          £4,029 / week

          Book View

          from £576 / night

            21

            Holiday farmhouse with swimming pool in San Casciano in Val di Pesa

            Province of Florence / San Casciano in Val di Pesa

            4 8 4 nights min

            • 4 bedrooms
            • sleeps 8
            • 4 nights min
            • Nearest beach 80 km
            • Swimming pool
            • Child friendly

            from £339 / night

            £2,370 / week

            Book View

            from £339 / night

              13

              Holiday b&b with shared pool in San Casciano in Val di Pesa

              Province of Florence / San Casciano in Val di Pesa

              1 4 1 night min

              • 1 bedroom
              • sleeps 4
              • 1 night min
              • Nearest beach 90 km
              • Swimming pool
              • Child friendly

              from £51 / night

              £353 - £466 / week

              Book View

              from £51 / night

                10

                Apartment rental in San Casciano in Val di Pesa

                Province of Florence / San Casciano in Val di Pesa

                1 5 1 night min

                • 1 bedroom
                • sleeps 5
                • 1 night min
                • Child friendly
                • Air conditioning

                from £101 / night

                £182 / week

                Book View

                from £101 / night

                (1) Excellent 

                  32

                  Holiday apartment in San Casciano in Val di Pesa

                  Province of Florence / San Casciano in Val di Pesa

                  2 4 min stay varies

                  • 2 bedrooms
                  • sleeps 4
                  • min stay varies
                  • Child friendly
                  • Car not necessary
                  • Air conditioning

                  from £86 / night

                  £564 - £776 / week

                  Book View

                  from £86 / night

                  (32) Excellent 

                    26

                    San Casciano in Val di Pesa holiday farmhouse rental

                    Province of Florence / San Casciano in Val di Pesa

                    2 5 min stay varies

                    • 2 bedrooms
                    • sleeps 5
                    • min stay varies
                    • Nearest beach 83 km
                    • Suitable for children age 5+
                    • Car not necessary

                    from £86 / night

                    £554 - £927 / week

                    Book View

                    Responds fast!
                    avg. 59 minutes

                    from £86 / night

                    (4) Excellent 

                      15

                      Holiday farmhouse with swimming pool, tennis court in San Casciano in Val di Pesa

                      Province of Florence / San Casciano in Val di Pesa

                      2 6 min stay varies

                      • 2 bedrooms
                      • sleeps 6
                      • min stay varies
                      • Swimming pool
                      • Child friendly
                      • Pet friendly

                      from £86 / night

                      £600 - £1,093 / week

                      Book View

                      Responds fast!
                      avg. 3 hours 16 minutes

                      from £86 / night

                      (1) Very Good 

                        23

                        San Casciano in Val di Pesa holiday finca rental

                        Province of Florence / San Casciano in Val di Pesa

                        1 4 3 nights min

                        • 1 bedroom
                        • sleeps 4
                        • 3 nights min
                        • Child friendly
                        • Ask about pets

                        from £66 / night

                        £413 / week

                        Book View

                        from £66 / night

                        (2) Very Good 

                          10

                          Holiday apartment in San Casciano in Val di Pesa

                          Province of Florence / San Casciano in Val di Pesa

                          2 4 1 night min

                          • 2 bedrooms
                          • sleeps 4
                          • 1 night min
                          • Child friendly
                          • Air conditioning
                          • Ask about pets

                          from £90 / night

                          £625 / week

                          Book View

                          from £90 / night

                            99

                            San Casciano in Val di Pesa holiday apartment rental

                            Province of Florence / San Casciano in Val di Pesa

                            13 27 3 nights min

                            • 13 bedrooms
                            • sleeps 27
                            • 3 nights min
                            • Nearest beach 90 km
                            • Swimming pool
                            • Child friendly

                            from £637 / night

                            £3,917 / week

                            Book View

                            from £637 / night

                              26

                              Holiday villa accommodation

                              Province of Florence / San Casciano in Val di Pesa

                              11 26 min stay varies

                              • 11 bedrooms
                              • sleeps 26
                              • min stay varies
                              • Swimming pool
                              • Child friendly
                              • Air conditioning

                              from £1,108 / night

                              £7,453 - £9,014 / week

                              Book View

                              from £1,108 / night

                                29

                                Holiday apartment in San Casciano in Val di Pesa

                                Province of Florence / San Casciano in Val di Pesa

                                1 4 1 night min

                                • 1 bedroom
                                • sleeps 4
                                • 1 night min
                                • Child friendly

                                from £61 / night

                                £353 - £564 / week

                                Book View

                                from £61 / night

                                  14

                                  B&b rental in San Casciano in Val di Pesa

                                  Province of Florence / San Casciano in Val di Pesa

                                  8 16 1 night min

                                  • 8 bedrooms
                                  • sleeps 16
                                  • 1 night min
                                  • Child friendly
                                  • Air conditioning
                                  • Pet friendly

                                  from £76 / night

                                  £529 / week

                                  Book View

                                  from £76 / night

                                  (2) Excellent 

                                    23

                                    Villa rental in San Casciano in Val di Pesa with swimming pool

                                    Province of Florence / San Casciano in Val di Pesa

                                    4 12 7 nights min

                                    • 4 bedrooms
                                    • sleeps 12
                                    • 7 nights min
                                    • Swimming pool
                                    • Child friendly
                                    • Air conditioning

                                    from £410 / night

                                    £2,871 / week

                                    Book View

                                    from £410 / night

                                      4

                                      Holiday b&b rental

                                      Province of Florence / San Casciano in Val di Pesa

                                      4 3 1 night min

                                      • 4 bedrooms
                                      • sleeps 3
                                      • 1 night min
                                      • Nearest beach 110 km
                                      • Child friendly
                                      • Private garden

                                      from £76 / night

                                      £529 / week

                                      Book View

                                      from £76 / night

                                      (3) Very Good 

                                        24

                                        Holiday townhouse with shared pool in Chiesanuova

                                        San Casciano in Val di Pesa / Chiesanuova

                                        1 3 3 nights min

                                        • 1 bedroom
                                        • sleeps 3
                                        • 3 nights min
                                        • Swimming pool
                                        • Child friendly
                                        • Air conditioning

                                        from £76 / night

                                        £554 / week

                                        Book View

                                        from £76 / night

                                        (2) Very Good 

                                          29

                                          San Casciano in Val di Pesa holiday villa rental

                                          Province of Florence / San Casciano in Val di Pesa

                                          3 6 3 nights min

                                          • 3 bedrooms
                                          • sleeps 6
                                          • 3 nights min
                                          • Swimming pool
                                          • Child friendly
                                          • Private garden

                                          from £252 / night

                                          £1,511 - £1,864 / week

                                          Book View

                                          Responds fast!
                                          avg. 2 hours 55 minutes

                                          from £252 / night

                                            12

                                            Holiday apartment with shared pool in San Casciano in Val di Pesa

                                            Province of Florence / San Casciano in Val di Pesa

                                            2 4 2 nights min

                                            • 2 bedrooms
                                            • sleeps 4
                                            • 2 nights min
                                            • Swimming pool
                                            • Child friendly
                                            • Pet friendly

                                            from £81 / night

                                            £564 / week

                                            Book View

                                            from £81 / night

                                            (4) Excellent 

                                              22

                                              Holiday apartment in San Casciano in Val di Pesa

                                              Province of Florence / San Casciano in Val di Pesa

                                              1 3 4 nights min

                                              • 1 bedroom
                                              • sleeps 3
                                              • 4 nights min
                                              • Child friendly
                                              • Air conditioning
                                              • Private garden

                                              from £61 / night

                                              £403 / week

                                              Book View

                                              from £61 / night

                                                18

                                                San Casciano in Val di Pesa holiday villa rental

                                                Province of Florence / San Casciano in Val di Pesa

                                                2 5 7 nights min

                                                • 2 bedrooms
                                                • sleeps 5
                                                • 7 nights min
                                                • Nearest beach 100 km
                                                • Child friendly
                                                • Air conditioning

                                                from £65 / night

                                                £454 / week

                                                Book View

                                                from £65 / night

                                                (2) Excellent 

                                                  24

                                                  Holiday home with swimming pool in San Casciano in Val di Pesa

                                                  Province of Florence / San Casciano in Val di Pesa

                                                  2 4 min stay varies

                                                  • 2 bedrooms
                                                  • sleeps 4
                                                  • min stay varies
                                                  • Swimming pool
                                                  • Child friendly
                                                  • Private garden

                                                  from £111 / night

                                                  £846 - £1,174 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 3 hours 59 minutes

                                                  from £111 / night

                                                  (1) Very Good 

                                                    21

                                                    Townhouse rental in Chiesanuova with shared pool

                                                    San Casciano in Val di Pesa / Chiesanuova

                                                    1 3 2 nights min

                                                    • 1 bedroom
                                                    • sleeps 3
                                                    • 2 nights min
                                                    • Swimming pool
                                                    • Child friendly
                                                    • Private garden

                                                    from £71 / night

                                                    £403 / week

                                                    Book View

                                                    from £71 / night

                                                    (1) Very Good 

                                                      32

                                                      Holiday apartment in San Casciano in Val di Pesa

                                                      Province of Florence / San Casciano in Val di Pesa

                                                      2 4 min stay varies

                                                      • 2 bedrooms
                                                      • sleeps 4
                                                      • min stay varies
                                                      • Child friendly
                                                      • Car not necessary
                                                      • Air conditioning

                                                      from £86 / night

                                                      £600 - £776 / week

                                                      Book View

                                                      from £86 / night

                                                      (1) Very Good 

                                                        16

                                                        Holiday apartment rental

                                                        Province of Florence / San Casciano in Val di Pesa

                                                        1 2 4 nights min

                                                        • 1 bedroom
                                                        • sleeps 2
                                                        • 4 nights min
                                                        • Nearest beach 100 km
                                                        • Child friendly
                                                        • Air conditioning

                                                        from £56 / night

                                                        £363 / week

                                                        Book View

                                                        from £56 / night

                                                          13

                                                          B&b rental in San Casciano in Val di Pesa

                                                          Province of Florence / San Casciano in Val di Pesa

                                                          1 2 3 nights min

                                                          • 1 bedroom
                                                          • sleeps 2
                                                          • 3 nights min
                                                          • Nearest beach 90 km
                                                          • Child friendly
                                                          • Pet friendly

                                                          from £81 / night

                                                          £559 / week

                                                          Book View

                                                          from £81 / night

                                                            25

                                                            Holiday apartment with shared pool in San Casciano in Val di Pesa

                                                            Province of Florence / San Casciano in Val di Pesa

                                                            2 6 3 nights min

                                                            • 2 bedrooms
                                                            • sleeps 6
                                                            • 3 nights min
                                                            • Swimming pool
                                                            • Child friendly
                                                            • Pet friendly

                                                            from £121 / night

                                                            £846 - £1,058 / week

                                                            Book View

                                                            from £121 / night

                                                              9

                                                              San Casciano in Val di Pesa holiday b&b rental

                                                              Province of Florence / San Casciano in Val di Pesa

                                                              9 2 1 night min

                                                              • 9 bedrooms
                                                              • sleeps 2
                                                              • 1 night min
                                                              • Swimming pool
                                                              • Air conditioning
                                                              • Ask about pets

                                                              from £135 / night

                                                              £898 / week

                                                              Book View

                                                              from £135 / night

                                                                83

                                                                Villa rental in San Casciano in Val di Pesa with swimming pool

                                                                Province of Florence / San Casciano in Val di Pesa

                                                                4 12 7 nights min

                                                                • 4 bedrooms
                                                                • sleeps 12
                                                                • 7 nights min
                                                                • Nearest beach 115 km
                                                                • Swimming pool
                                                                • Child friendly

                                                                from £189 / night

                                                                £1,320 - £2,287 / week

                                                                Enquire View

                                                                from £189 / night

                                                                (1) Excellent 

                                                                  57

                                                                  Campoli in Chianti holiday cottage rental

                                                                  San Casciano in Val di Pesa / Campoli in Chianti

                                                                  3 6 3 nights min

                                                                  • 3 bedrooms
                                                                  • sleeps 6
                                                                  • 3 nights min
                                                                  • Nearest beach 120 km
                                                                  • Child friendly
                                                                  • Ask about pets

                                                                  from £131 / night

                                                                  £877 / week

                                                                  Book View

                                                                  from £131 / night

                                                                    17

                                                                    Holiday townhouse in San Casciano in Val di Pesa

                                                                    Province of Florence / San Casciano in Val di Pesa

                                                                    1 2 2 nights min

                                                                    • 1 bedroom
                                                                    • sleeps 2
                                                                    • 2 nights min
                                                                    • Air conditioning
                                                                    • Pet friendly
                                                                    • Private garden

                                                                    from £46 / night

                                                                    £333 / week

                                                                    Book View

                                                                    from £46 / night

                                                                      19

                                                                      San Casciano in Val di Pesa holiday villa rental

                                                                      Province of Florence / San Casciano in Val di Pesa

                                                                      2 4 5 nights min

                                                                      • 2 bedrooms
                                                                      • sleeps 4
                                                                      • 5 nights min
                                                                      • Swimming pool
                                                                      • Child friendly
                                                                      • Private garden

                                                                      from £383 / night

                                                                      £2,679 / week

                                                                      Book View

                                                                      from £383 / night

                                                                      (4) Excellent 

                                                                        39

                                                                        San Casciano in Val di Pesa holiday finca accommodation

                                                                        Province of Florence / San Casciano in Val di Pesa

                                                                        4 6 min stay varies

                                                                        • 4 bedrooms
                                                                        • sleeps 6
                                                                        • min stay varies
                                                                        • Nearest beach 120 km
                                                                        • Swimming pool
                                                                        • Child friendly

                                                                        from £141 / night

                                                                        £907 - £1,612 / week

                                                                        Book View

                                                                        from £141 / night

                                                                        (3) Excellent 

                                                                          19

                                                                          Holiday farmhouse rental

                                                                          Province of Florence / San Casciano in Val di Pesa

                                                                          2 4 7 nights min

                                                                          • 2 bedrooms
                                                                          • sleeps 4
                                                                          • 7 nights min
                                                                          • Swimming pool
                                                                          • Child friendly
                                                                          • Air conditioning

                                                                          from £288 / night

                                                                          £2,017 / week

                                                                          Book View

                                                                          Responds fast!
                                                                          avg. 42 minutes

                                                                          from £288 / night

                                                                            20

                                                                            Holiday villa with shared pool in Mercatale di Val di Pesa

                                                                            San Casciano in Val di Pesa / Mercatale di Val di Pesa

                                                                            3 7 7 nights min

                                                                            • 3 bedrooms
                                                                            • sleeps 7
                                                                            • 7 nights min
                                                                            • Swimming pool
                                                                            • Child friendly
                                                                            • Air conditioning

                                                                            from £1,439 / night

                                                                            £10,071 / week

                                                                            Book View

                                                                            from £1,439 / night

                                                                            (2) Excellent 

                                                                              19

                                                                              Holiday apartment with shared pool in Mercatale di Val di Pesa

                                                                              San Casciano in Val di Pesa / Mercatale di Val di Pesa

                                                                              2 6 7 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 6
                                                                              • 7 nights min
                                                                              • Swimming pool
                                                                              • Child friendly
                                                                              • Air conditioning

                                                                              from £1,439 / night

                                                                              £10,071 / week

                                                                              Book View

                                                                              from £1,439 / night

                                                                                27

                                                                                Holiday villa with swimming pool in San Casciano in Val di Pesa

                                                                                Province of Florence / San Casciano in Val di Pesa

                                                                                11 15 7 nights min

                                                                                • 11 bedrooms
                                                                                • sleeps 15
                                                                                • 7 nights min
                                                                                • Nearest beach 120 km
                                                                                • Swimming pool
                                                                                • Child friendly

                                                                                from £993 / night

                                                                                £6,949 - £8,268 / week

                                                                                Enquire View

                                                                                from £993 / night

                                                                                (1) Excellent 

                                                                                  15

                                                                                  Holiday b&b in San Casciano in Val di Pesa

                                                                                  Province of Florence / San Casciano in Val di Pesa

                                                                                  1 2 1 night min

                                                                                  • 1 bedroom
                                                                                  • sleeps 2
                                                                                  • 1 night min
                                                                                  • Private garden

                                                                                  from £91 / night

                                                                                  £585 / week

                                                                                  Book View

                                                                                  from £91 / night

                                                                                  Top Destination reviews

                                                                                  Tenuta Villa Barberino Apartment The Campolino She
                                                                                  Fantastic Villa with amazing views!

                                                                                  We stayed at this villa with our teenage children and we all loved the tranquil setting on this working vineyard. The views are amazing and the house stylishly decorated. The aircon in both bedrooms was really welcome and the Wifi is useful. Antonio's communication was excellent and he is on hand if needed during your stay but very much in the background, a perfect mix. You are assigned your own private cabana within the garden with a stunning view and comfortable loungers, dining table and chairs under a permanent shade. This was really private and well thought out and thoroughly relaxing. We had access to the pool, which although shared with the other apartment and villa was never crowded. I cannot recommend this place highly enough for a relaxing holiday - away from it all and yet within close driving distance from Florence and Sienna and charming towns and pretty villages. Many thanks for such a great stay!see more
                                                                                  Villa Il Portico
                                                                                  A beautiful haven

                                                                                  Villa il Portico, a.k.a. Montepaldi a.k.a.Fume - whichever is the proper name - was a slice of paradise and a welcome haven during some unexpected vacation crises. I traveled to Tuscany with extended family, 10 people, and we were all stunned by how beautiful the property is. When we arrived we couldn't believe how much more amazing it is; photos cannot do it justice. The beautiful views will stay with you forever. The location is really great - you feel away from everything but a grocery store with everything you could need is only a 5 minute drive away and Florence is only a 20 to 30 minute drive or bus ride. My family did experience a bit of trauma on our trip; no fault of the Villa - my 80 year old father had a bad fall while sightseeing and ended up in the hospital for two days - Manola, Loredana and Lupo were all so gracious, caring and helpful. Luckily, my Dad seems to have recovered fully and we have beautiful memories of our stay at the villa. We hope to return again sometime.see more
                                                                                  Delicious country house
                                                                                  Relaxing, Welcoming, Wonderful place to stay.

                                                                                  We stayed in the apartment in June this year and would definitely return again. Upon arrival we were greeted warmly with a welcome pack of delicious cake, wine, fruit etc. The apartment was a good size and the bedroom was beautiful. Throughout our stay we had the windows opened and had the beautiful smell of jasmine throughout the room. The views were spectacular and we throughly enjoyed every minute of our stay. The location was excellent to get to all the points of interest in Tuscany and we were kindly provided with details of where to park etc upon visiting the major cities. We had an amazing time and cannot wait to return in the future.see more
                                                                                  Atelier 1
                                                                                  What a beautiful place to spend our holiday

                                                                                  Our apartment was situated on a large estate Villa Licia with beautiful classic gardens. We really enjoyed the spacious house, everything was taken well care of with perfect furniture and 100% cleanliness. Was near Florence and Siena so we had all chance to see the treasures. We come back for sure … see more
                                                                                  Honeymoon apartment in country villa
                                                                                  Holiday rental that ticked all the right boxes!

                                                                                  We chose Borgo Rosa for our long term stay in Italy, as it fitted all the criteria that were important to us., We planned to stay in Tuscany for 2 to 3months, so we were looking for accomodation that was reasonably priced, self contained and comfortable, with mod cons such as washing machine and dryer, air conditions and heating, a functional kitchen, pleasant surrounds and a swimming pool to cool off in during hot August days. We also wanted to be within reasonable driving distance from all the towns and villages that we wanted to visit. We also wanted to be able to walk to a nearby village for coffee ( very important ) and to be able to shop for staples, without necessarily having to drive. Borgo Rosa is situated in Chianti, near San Casciano in Val di Pesa, and Mercatale was our nearest village. We were a 5 minute drive from the autostrada between Siena and Florence. Less than half an hour from Florence and 45 minutes from Siena. Perfect! We stayed initially in Suite 3, a one bedroom appartment, and later in the season moved to Suite 4, with two bedrooms. Both were perfect for our needs, tastefully decorated and most comfortable. Each had, like all the other suites, a private garden area and/or terrace which we could use for outdoor eating, and were within the larger property of olive groves, with pool and a BBQ! Very important for Aussies! Our fellow guests were charming, some with families and some gravelling in groups, of diverse origins, which made life interesting. Our host, Andrea was perfectly delightful. He was full of information re local places, events and most importantly, eating places, and was happy to drive us to where we wanted to go until we organised a car. He went out of his way to give help when needed, and we would look forward to hearing his morning " hello" when checking on us. My one and only complaint would be that Andrea was keen to practise his English, when I was keen to practise my Italian! Having grown up and lived in Floorence, meant that he was full of inside information from where to park, how to avoid limited traffic zones and restaurants frequented by locals, with wonderful food. We ended by becoming very good friends and we wouldn't hesitate to return should we be lucky enough to do so.see more
                                                                                  Farmhouse in a traditional Tuscan country Villa
                                                                                  Bravissimo

                                                                                  My daughters and I went on the trip of a lifetime with dear friends to Tuscany. We had the great fortune to stay at the breathtaking Il Frantoio di Villa Caserotta. The villa was nothing short of spectacular. The property was beautifully landscaped, the apartment well appointed with every amenity, and we were minutes from Florence, the farmers market, the coop (grocery store) and the train station. The pool was a highlight, as well as the outdoor bbq and patio dining area. We often prepared meals in the kitchen which had every item you could possibly need. Andrea and Claudia, the property owners, were wonderful hosts and so attentive and gracious in helping us plan our day trips and restaurant choices. We haven't stopped talking about the villa since we've returned, and hope to return soon.see more

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