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382 Holiday homes

(6) Excellent 

    29

    Holiday apartment with shared pool in Gaiole in Chianti

    Province of Siena / Gaiole in Chianti

    2 6 7 nights min

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

    from £108 / night

    £753 - £1,099 / week

    Book View

    Responds fast!
    avg. 1 hour 40 minutes

    from £108 / night

    (7) Very Good 

      43

      Montefienali holiday home accommodation

      Gaiole in Chianti / Montefienali

      3 6 min stay varies

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

      from £55 / night

      £314 / week

      Book View

      Responds fast!
      avg. 1 hour 19 minutes

      from £55 / night

      (8) Excellent 

        20

        Apartment accommodation in Gaiole in Chianti with shared pool

        Province of Siena / Gaiole in Chianti

        2 6 2 nights min

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

        from £81 / night

        £573 / week

        Book View

        from £81 / night

        (14) Very Good 

          39

          Holiday villa with swimming pool, tennis court in Gaiole in Chianti

          Province of Siena / Gaiole in Chianti

          2 5 min stay varies

          • 2 bedrooms
          • sleeps 5
          • min stay varies
          • Nearest beach 110 km
          • Swimming pool
          • Child friendly

          from £206 / night

          £1,447 - £2,411 / week

          Book View

          Responds fast!
          avg. 3 hours 56 minutes

          from £206 / night

          (3) Excellent 

            28

            Gaiole in Chianti holiday barn let

            Province of Siena / Gaiole in Chianti

            2 4 2 nights min

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

            from £111 / night

            £704 / week

            Book View

            from £111 / night

            (14) Excellent 

              34

              Holiday apartment with shared pool in Gaiole in Chianti

              Province of Siena / Gaiole in Chianti

              3 8 min stay varies

              • 3 bedrooms
              • sleeps 8
              • min stay varies
              • Swimming pool
              • Child friendly
              • Air conditioning

              from £200 / night

              £1,200 - £1,600 / week

              Book View

              from £200 / night

                17

                Nusenna holiday apartment rental

                Gaiole in Chianti / Nusenna

                2 5 min stay varies

                • 2 bedrooms
                • sleeps 5
                • min stay varies
                • Swimming pool
                • Child friendly
                • Pet friendly

                from £81 / night

                £562 / week

                Book View

                from £81 / night

                (18) Excellent 

                  33

                  Holiday apartment with shared pool in Gaiole in Chianti

                  Province of Siena / Gaiole in Chianti

                  1 4 min stay varies

                  • 1 bedroom
                  • sleeps 4
                  • min stay varies
                  • Nearest beach 80 km
                  • Swimming pool
                  • Child friendly
                  “Comfort and relaxation in Chianti” We enjoyed everything about Casacorvo. The view from the terrace is still in our minds weeks after we returned. Those beautiful rolling hills and the view over to Barbischio. Great pool which, in September was very quiet. We visited Siena, Florence, San Gimignano, Arezzo andthe wine festival at Greve in Chianti. Nice local wine left by Phil was much appreciated. The facilities in the Borgo were great. Gaiole is lovely and friendly and you don't have to go far to find nice meals and bars.

                  from £125 / night

                  £575 - £775 / week

                  Book View

                  from £125 / night

                  (4) Excellent 

                    21

                    Holiday villa rental

                    Province of Siena / Gaiole in Chianti

                    2 7 min stay varies

                    • 2 bedrooms
                    • sleeps 7
                    • min stay varies
                    • Nearest beach 110 km
                    • Swimming pool
                    • Child friendly

                    from £91 / night

                    £452 - £1,004 / week

                    Book View

                    Responds fast!
                    avg. 27 minutes

                    from £91 / night

                      33

                      Apartment rental in Gaiole in Chianti with shared pool

                      Province of Siena / Gaiole in Chianti

                      2 5 7 nights min

                      • 2 bedrooms
                      • sleeps 5
                      • 7 nights min
                      • Nearest beach 107 km
                      • Swimming pool
                      • Child friendly

                      from £52 / night

                      £360 - £781 / week

                      Enquire View

                      from £52 / night

                        21

                        Holiday guest house in Montefienali

                        Gaiole in Chianti / Montefienali

                        2 6 min stay varies

                        • 2 bedrooms
                        • sleeps 6
                        • min stay varies
                        • Child friendly
                        • Ask about pets
                        • Private garden

                        from £55 / night

                        £352 / week

                        Book View

                        Responds fast!
                        avg. 1 hour 19 minutes

                        from £55 / night

                          25

                          Apartment rental in Gaiole in Chianti with shared pool, golf nearby

                          Province of Siena / Gaiole in Chianti

                          2 5 7 nights min

                          • 2 bedrooms
                          • sleeps 5
                          • 7 nights min
                          • Nearest beach 107 km
                          • Swimming pool
                          • Child friendly

                          from £52 / night

                          £360 - £781 / week

                          Enquire View

                          from £52 / night

                            33

                            Gaiole in Chianti holiday apartment rental

                            Province of Siena / Gaiole in Chianti

                            2 5 7 nights min

                            • 2 bedrooms
                            • sleeps 5
                            • 7 nights min
                            • Nearest beach 107 km
                            • Swimming pool
                            • Child friendly

                            from £52 / night

                            £360 - £781 / week

                            Enquire View

                            from £52 / night

                            (3) Average 

                              12

                              Holiday apartment with shared pool in Gaiole in Chianti

                              Province of Siena / Gaiole in Chianti

                              1 2 7 nights min

                              • 1 bedroom
                              • sleeps 2
                              • 7 nights min
                              • Swimming pool
                              • Child friendly
                              • Pet friendly

                              from £85 / night

                              £593 / week

                              Book View

                              from £85 / night

                              (1) Excellent 

                                62

                                Holiday villa in Gaiole in Chianti

                                Province of Siena / Gaiole in Chianti

                                5 10 7 nights min

                                • 5 bedrooms
                                • sleeps 10
                                • 7 nights min
                                • Child friendly
                                • Pet friendly

                                from £474 / night

                                £3,313 / week

                                Book View

                                from £474 / night

                                  16

                                  Holiday apartment with shared pool in Nusenna

                                  Gaiole in Chianti / Nusenna

                                  2 4 min stay varies

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

                                  from £71 / night

                                  £493 / week

                                  Book View

                                  from £71 / night

                                    13

                                    Nusenna holiday apartment rental

                                    Gaiole in Chianti / Nusenna

                                    2 5 min stay varies

                                    • 2 bedrooms
                                    • sleeps 5
                                    • min stay varies
                                    • Swimming pool
                                    • Child friendly
                                    • Pet friendly

                                    from £91 / night

                                    £633 / week

                                    Book View

                                    from £91 / night

                                      18

                                      Gaiole in Chianti holiday apartment rental

                                      Province of Siena / Gaiole in Chianti

                                      2 5 7 nights min

                                      • 2 bedrooms
                                      • sleeps 5
                                      • 7 nights min
                                      • Nearest beach 107 km
                                      • Swimming pool
                                      • Child friendly

                                      from £52 / night

                                      £360 - £781 / week

                                      Enquire View

                                      from £52 / night

                                      (1) Excellent 

                                        24

                                        Holiday apartment with shared pool in Gaiole in Chianti

                                        Province of Siena / Gaiole in Chianti

                                        4 10 min stay varies

                                        • 4 bedrooms
                                        • sleeps 10
                                        • min stay varies
                                        • Nearest beach 80 km
                                        • Swimming pool
                                        • Child friendly

                                        from £350 / night

                                        £2,000 - £2,400 / week

                                        Book View

                                        from £350 / night

                                          15

                                          Gaiole in Chianti holiday farmhouse rental

                                          Province of Siena / Gaiole in Chianti

                                          9 22 1 night min

                                          • 9 bedrooms
                                          • sleeps 22
                                          • 1 night min
                                          • Child friendly
                                          • Private garden

                                          from £77 / night

                                          £502 - £5,842 / week

                                          Book View

                                          from £77 / night

                                            26

                                            Holiday villa with swimming pool in Gaiole in Chianti

                                            Province of Siena / Gaiole in Chianti

                                            4 12 min stay varies

                                            • 4 bedrooms
                                            • sleeps 12
                                            • min stay varies
                                            • Swimming pool
                                            • Child friendly
                                            • Pet friendly

                                            from £302 / night

                                            £2,110 / week

                                            Book View

                                            Responds fast!
                                            avg. 11 minutes

                                            from £302 / night

                                              15

                                              Holiday apartment in Gaiole in Chianti

                                              Province of Siena / Gaiole in Chianti

                                              1 4 1 night min

                                              • 1 bedroom
                                              • sleeps 4
                                              • 1 night min
                                              • Child friendly
                                              • Air conditioning
                                              • Pet friendly

                                              from £73 / night

                                              £506 / week

                                              Book View

                                              from £73 / night

                                                17

                                                Nusenna holiday apartment let

                                                Gaiole in Chianti / Nusenna

                                                4 8 1 night min

                                                • 4 bedrooms
                                                • sleeps 8
                                                • 1 night min
                                                • Swimming pool
                                                • Child friendly
                                                • Pet friendly

                                                from £186 / night

                                                £1,300 / week

                                                Book View

                                                from £186 / night

                                                (1) Excellent 

                                                  30

                                                  Villa rental in Gaiole in Chianti with swimming pool

                                                  Province of Siena / Gaiole in Chianti

                                                  7 14 7 nights min

                                                  • 7 bedrooms
                                                  • sleeps 14
                                                  • 7 nights min
                                                  • Nearest beach 100 km
                                                  • Swimming pool
                                                  • Child friendly

                                                  from £604 / night

                                                  £4,227 / week

                                                  Book View

                                                  from £604 / night

                                                    12

                                                    Holiday villa in Nusenna

                                                    Gaiole in Chianti / Nusenna

                                                    2 4 3 nights min

                                                    • 2 bedrooms
                                                    • sleeps 4
                                                    • 3 nights min
                                                    • Child friendly

                                                    from £162 / night

                                                    £1,132 - £1,413 / week

                                                    Book View

                                                    from £162 / night

                                                      20

                                                      Gaiole in Chianti holiday home rental

                                                      Province of Siena / Gaiole in Chianti

                                                      2 4 7 nights min

                                                      • 2 bedrooms
                                                      • sleeps 4
                                                      • 7 nights min
                                                      • Swimming pool
                                                      • Child friendly
                                                      • Ask about pets

                                                      from £111 / night

                                                      £774 / week

                                                      Book View

                                                      from £111 / night

                                                        37

                                                        Holiday home rental

                                                        Province of Siena / Gaiole in Chianti

                                                        5 10 5 nights min

                                                        • 5 bedrooms
                                                        • sleeps 10
                                                        • 5 nights min
                                                        • Nearest beach 124 km
                                                        • Swimming pool
                                                        • Child friendly

                                                        from £211 / night

                                                        £1,477 / week

                                                        Book View

                                                        from £211 / night

                                                        (30) Excellent 

                                                          71

                                                          Holiday villa in Gaiole in Chianti

                                                          Province of Siena / Gaiole in Chianti

                                                          5 13 min stay varies

                                                          • 5 bedrooms
                                                          • sleeps 13
                                                          • min stay varies
                                                          • Nearest beach 40 km
                                                          • Swimming pool
                                                          • Child friendly
                                                          “Idyllic stay in very comfortable, beautifully furnished house” Driving up to La Pratola you get a great view of the house as you climb the hill to it, but nothing could have prepared us for the amazing view back down the hill and across the valley from the infinity pool. Breathtaking. We were supplied with amazing food and service by a really sweet lady who looked after us well, whilst also discretely blending in, never making us feel self-conscious, and the maid service was excellent. Nearby Gaiole has all you could need, and is pretty, but Florence and Siena are wonderfully close by for a day trip. There are good walks and bike rides ( or runs) straight out from the house, but we just wanted to chill out by the pool or in the lovely courtyard most of the time. The Interior is very comfortably furnished to a high standard, with plenty of places for people to relax, so if you are in a big group it works well to go off and do you own thing for a while - the upstairs living room is great- huge squishy leather sofas and a big screen TV. We particularly enjoyed the pool table too. We weren't disappointed by La Pratola and would happily go back there again.

                                                          from £1,254 / night

                                                          £7,730 - £12,305 / week

                                                          Book View

                                                          from £1,254 / night

                                                          Great rentals within 20 miles that match your search

                                                          Distance approx 16.91 miles from Gaiole in Chianti

                                                            16

                                                            Reggello holiday apartment let

                                                            Province of Florence / Reggello

                                                            2 5 3 nights min

                                                            • 2 bedrooms
                                                            • sleeps 5
                                                            • 3 nights min
                                                            • Nearest beach 100 km
                                                            • Child friendly
                                                            • Pet friendly

                                                            from £150 / night

                                                            £847 - £1,265 / week

                                                            Book View

                                                            from £150 / night

                                                            Distance approx 4.48 miles from Gaiole in Chianti Show on Map

                                                              42

                                                              Moncioni holiday apartment rental

                                                              Montevarchi / Moncioni

                                                              1 2 3 nights min

                                                              • 1 bedroom
                                                              • sleeps 2
                                                              • 3 nights min
                                                              • Swimming pool
                                                              • Pet friendly

                                                              from £80 / night

                                                              £548 / week

                                                              Book View

                                                              from £80 / night

                                                              Distance approx 4.57 miles from Gaiole in Chianti Show on Map

                                                                55

                                                                Moncioni holiday apartment rental

                                                                Montevarchi / Moncioni

                                                                1 2 3 nights min

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

                                                                from £125 / night

                                                                £840 / week

                                                                Book View

                                                                from £125 / night

                                                                Distance approx 19.49 miles from Gaiole in Chianti

                                                                  83

                                                                  Home rental in Impruneta with swimming pool

                                                                  Province of Florence / Impruneta

                                                                  4 8 7 nights min

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

                                                                  from £200 / night

                                                                  £1,400 - £1,820 / week

                                                                  Book View

                                                                  from £200 / night

                                                                  Distance approx 8.6 miles from Gaiole in Chianti Show on Map

                                                                    24

                                                                    Colle di Val d'Elsa holiday apartment rental

                                                                    Province of Siena / Colle di Val d'Elsa

                                                                    3 5 7 nights min

                                                                    • 3 bedrooms
                                                                    • sleeps 5
                                                                    • 7 nights min
                                                                    • Swimming pool
                                                                    • Child friendly
                                                                    • Air conditioning

                                                                    from £285 / night

                                                                    £2,000 / week

                                                                    Book View

                                                                    from £285 / night

                                                                    Distance approx 13.36 miles from Gaiole in Chianti

                                                                      46

                                                                      Holiday b&b in Pian di Sco

                                                                      Castelfranco Piandisco / Pian di Sco

                                                                      4 9 3 nights min

                                                                      • 4 bedrooms
                                                                      • sleeps 9
                                                                      • 3 nights min
                                                                      • Swimming pool
                                                                      • Child friendly
                                                                      • Pet friendly

                                                                      from £250 / night

                                                                      £1,600 / week

                                                                      Book View

                                                                      from £250 / night

                                                                      Distance approx 7.73 miles from Gaiole in Chianti Show on Map

                                                                      (1) Excellent 

                                                                        30

                                                                        Holiday hotel apartment in Montebenichi

                                                                        Bucine / Montebenichi

                                                                        17 40 3 nights min

                                                                        • 17 bedrooms
                                                                        • sleeps 40
                                                                        • 3 nights min
                                                                        • Child friendly
                                                                        • Air conditioning
                                                                        • Ask about pets

                                                                        from £3,234 / night

                                                                        £16,499 / week

                                                                        Book View

                                                                        from £3,234 / night

                                                                        Distance approx 16.01 miles from Gaiole in Chianti

                                                                        (1) Excellent 

                                                                          50

                                                                          Holiday apartment in Rignano sull'Arno

                                                                          Province of Florence / Rignano sull'Arno

                                                                          2 6 min stay varies

                                                                          • 2 bedrooms
                                                                          • sleeps 6
                                                                          • min stay varies
                                                                          • Nearest beach 80 km
                                                                          • Child friendly
                                                                          • Pet friendly

                                                                          from £80 / night

                                                                          £490 - £1,020 / week

                                                                          Book View

                                                                          from £80 / night

                                                                          Distance approx 13.91 miles from Gaiole in Chianti

                                                                          (10) Excellent 

                                                                            25

                                                                            Apartment rental in Siena

                                                                            Province of Siena / Siena

                                                                            2 6 min stay varies

                                                                            • 2 bedrooms
                                                                            • sleeps 6
                                                                            • min stay varies
                                                                            • Nearest beach 100 km
                                                                            • Child friendly

                                                                            from £70 / night

                                                                            £450 - £730 / week

                                                                            Book View

                                                                            from £70 / night

                                                                            Distance approx 12.09 miles from Gaiole in Chianti

                                                                            (39) Excellent 

                                                                              30

                                                                              Greve in Chianti holiday villa rental

                                                                              Province of Florence / Greve in Chianti

                                                                              8 17 7 nights min

                                                                              • 8 bedrooms
                                                                              • sleeps 17
                                                                              • 7 nights min
                                                                              • Swimming pool
                                                                              • Child friendly
                                                                              • Air conditioning

                                                                              from £475 / night

                                                                              £3,321 - £8,446 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 3 hours 40 minutes

                                                                              from £475 / night

                                                                              Distance approx 6.29 miles from Gaiole in Chianti Show on Map

                                                                                27

                                                                                Apartment rental in Castellina In Chianti

                                                                                Province of Siena / Castellina In Chianti

                                                                                2 8 5 nights min

                                                                                • 2 bedrooms
                                                                                • sleeps 8
                                                                                • 5 nights min
                                                                                • Child friendly

                                                                                from £114 / night

                                                                                £794 / week

                                                                                Book View

                                                                                from £114 / night

                                                                                Distance approx 10.84 miles from Gaiole in Chianti

                                                                                  17

                                                                                  Holiday townhouse rental

                                                                                  Province of Florence / Greve in Chianti

                                                                                  1 2 7 nights min

                                                                                  • 1 bedroom
                                                                                  • sleeps 2
                                                                                  • 7 nights min
                                                                                  • Nearest beach 100 km
                                                                                  • Swimming pool
                                                                                  • Child friendly

                                                                                  from £100 / night

                                                                                  £700 / week

                                                                                  Book View

                                                                                  from £100 / night

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