Gaiole in Chianti apartment or villa with a high chair | Holiday Lettings

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788 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

    £756 - £1,104 / 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

      (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

        (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

          (13) Excellent 

            69

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

            Province of Siena / Gaiole in Chianti

            4 10 min stay varies

            • 4 bedrooms
            • sleeps 10
            • min stay varies
            • Nearest beach 110 km
            • Swimming pool
            • Child friendly
            “Excellent, spacious accommodation with a fantastic pool and view.” Very good, clear communication with the owner. Spacious, clean property Wonderful pool About 2 miles from villa to nearest village with bar, restaurant and small store Character property with high ceilings and lots of room Keeps cool indoors

            from £526 / night

            £3,459 - £5,655 / week

            Book View

            Responds fast!
            avg. 3 hours 56 minutes

            from £526 / 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

              (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 £207 / night

                £1,452 - £2,419 / week

                Book View

                Responds fast!
                avg. 3 hours 56 minutes

                from £207 / night

                  44

                  Holiday home with shared pool in Gaiole in Chianti

                  Province of Siena / Gaiole in Chianti

                  3 7 7 nights min

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

                  from £112 / night

                  £784 / week

                  Book View

                  from £112 / night

                    24

                    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
                    • Nearest beach 105 km
                    • Swimming pool
                    • Suitable for children age 5+

                    from £50 / night

                    £351 - £806 / week

                    Enquire View

                    from £50 / 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

                      (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

                        £3,316 / week

                        Book View

                        from £474 / night

                        (2) Very Good 

                          13

                          Holiday apartment with swimming pool in Gaiole in Chianti

                          Province of Siena / Gaiole in Chianti

                          2 4 2 nights min

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

                          from £56 / night

                          £352 - £915 / week

                          Book View

                          from £56 / 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

                              47

                              Gaiole in Chianti holiday apartment rental

                              Province of Siena / Gaiole in Chianti

                              2 4 7 nights min

                              • 2 bedrooms
                              • sleeps 4
                              • 7 nights min
                              • Nearest beach 100 km
                              • Child friendly
                              • Private garden

                              from £142 / night

                              £988 / week

                              Book View

                              from £142 / 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

                                £508 / week

                                Book View

                                from £73 / night

                                  4

                                  Holiday townhouse in Gaiole in Chianti

                                  Province of Siena / Gaiole in Chianti

                                  2 4 3 nights min

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

                                  from £201 / night

                                  £1,407 / week

                                  Book View

                                  from £201 / 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 £605 / night

                                    £4,232 / week

                                    Book View

                                    from £605 / night

                                    (1) Excellent 

                                      74

                                      Holiday villa in Barbischio

                                      Gaiole in Chianti / Barbischio

                                      3 6 7 nights min

                                      • 3 bedrooms
                                      • sleeps 6
                                      • 7 nights min
                                      • Ask owner if suitable for children
                                      • Air conditioning
                                      • Ask about pets

                                      from £383 / night

                                      £2,676 - £3,931 / week

                                      Book View

                                      from £383 / night

                                      (1) Excellent 

                                        26

                                        Home rental in Gaiole in Chianti with shared pool

                                        Province of Siena / Gaiole in Chianti

                                        1 2 3 nights min

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

                                        from £131 / night

                                        £803 - £1,014 / week

                                        Book View

                                        from £131 / night

                                          26

                                          Home accommodation in Gaiole in Chianti

                                          Province of Siena / Gaiole in Chianti

                                          1 2 2 nights min

                                          • 1 bedroom
                                          • sleeps 2
                                          • 2 nights min
                                          • Child friendly
                                          • Pet friendly

                                          from £71 / night

                                          £653 / week

                                          Book View

                                          from £71 / 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

                                            (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

                                              £7,732 - £12,308 / week

                                              Book View

                                              from £1,254 / night

                                              (2) Excellent 

                                                21

                                                Holiday home with shared pool in Gaiole in Chianti

                                                Province of Siena / Gaiole in Chianti

                                                2 5 6 nights min

                                                • 2 bedrooms
                                                • sleeps 5
                                                • 6 nights min
                                                • Swimming pool
                                                • Child friendly

                                                from £151 / night

                                                £980 / week

                                                Book View

                                                from £151 / night

                                                Great rentals within 20 miles that match your search

                                                Distance approx 14.96 miles from Gaiole in Chianti

                                                (17) Excellent 

                                                  37

                                                  Villa rental in Barberino Val d'Elsa with swimming pool

                                                  Province of Florence / Barberino Val d'Elsa

                                                  3 8 min stay varies

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

                                                  from £203 / night

                                                  £1,218 - £3,218 / week

                                                  Enquire View

                                                  from £203 / night

                                                  Distance approx 18.23 miles from Gaiole in Chianti

                                                  (4) Average 

                                                    28

                                                    Holiday villa with swimming pool in Bagno a Ripoli

                                                    Province of Florence / Bagno a Ripoli

                                                    8 16 min stay varies

                                                    • 8 bedrooms
                                                    • sleeps 16
                                                    • min stay varies
                                                    • Nearest beach 193 km
                                                    • Swimming pool
                                                    • Child friendly

                                                    from £1,332 / night

                                                    £6,987 - £8,724 / week

                                                    Enquire View

                                                    from £1,332 / night

                                                    Distance approx 9.4 miles from Gaiole in Chianti

                                                    (2) Very Good 

                                                      30

                                                      Holiday home with swimming pool in San Donato in Poggio

                                                      Tavarnelle Val di Pesa / San Donato in Poggio

                                                      3 6 min stay varies

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

                                                      from £193 / night

                                                      £1,252 - £1,647 / week

                                                      Book View

                                                      from £193 / night

                                                      Distance approx 16.66 miles from Gaiole in Chianti

                                                        28

                                                        Holiday villa with swimming pool in Asciano

                                                        Province of Siena / Asciano

                                                        4 10 2 nights min

                                                        • 4 bedrooms
                                                        • sleeps 10
                                                        • 2 nights min
                                                        • Nearest beach 100 km
                                                        • Swimming pool
                                                        • Child friendly

                                                        from £301 / night

                                                        £2,106 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 3 hours 38 minutes

                                                        from £301 / night

                                                        Distance approx 12.01 miles from Gaiole in Chianti

                                                          8

                                                          Holiday apartment in Poggibonsi

                                                          Province of Siena / Poggibonsi

                                                          2 5 3 nights min

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

                                                          from £93 / night

                                                          £602 / week

                                                          Book View

                                                          from £93 / night

                                                          Distance approx 14.32 miles from Gaiole in Chianti

                                                          (2) Average 

                                                            32

                                                            Holiday farmhouse with shared pool in San Giustino Valdarno

                                                            Province of Arezzo / San Giustino Valdarno

                                                            1 2 3 nights min

                                                            • 1 bedroom
                                                            • sleeps 2
                                                            • 3 nights min
                                                            • Nearest beach 110 km
                                                            • Swimming pool
                                                            • Child friendly

                                                            from £76 / night

                                                            £522 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 2 hours 12 minutes

                                                            from £76 / night

                                                            Distance approx 19.74 miles from Gaiole in Chianti

                                                              7

                                                              Holiday apartment in Certaldo

                                                              Province of Florence / Certaldo

                                                              2 4 2 nights min

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

                                                              from £131 / night

                                                              £602 / week

                                                              Book View

                                                              from £131 / night

                                                              Distance approx 16 miles from Gaiole in Chianti

                                                                23

                                                                Holiday castle with swimming pool in Monte San Savino

                                                                Province of Arezzo / Monte San Savino

                                                                11 25 4 nights min

                                                                • 11 bedrooms
                                                                • sleeps 25
                                                                • 4 nights min
                                                                • Swimming pool
                                                                • Child friendly
                                                                • Air conditioning

                                                                from £988 / night

                                                                £6,517 / week

                                                                Book View

                                                                from £988 / night

                                                                Distance approx 16.81 miles from Gaiole in Chianti

                                                                (16) Very Good 

                                                                  46

                                                                  Holiday hotel apartment in Impruneta

                                                                  Province of Florence / Impruneta

                                                                  1 4 3 nights min

                                                                  • 1 bedroom
                                                                  • sleeps 4
                                                                  • 3 nights min
                                                                  • Child friendly
                                                                  • Car not necessary
                                                                  • Pet friendly

                                                                  from £60 / night

                                                                  £394 - £531 / week

                                                                  Book View

                                                                  from £60 / night

                                                                  Distance approx 12.15 miles from Gaiole in Chianti

                                                                    12

                                                                    Holiday apartment with shared pool in Castelfranco di Sopra

                                                                    Castelfranco Piandisco / Castelfranco di Sopra

                                                                    1 2 1 night min

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

                                                                    from £71 / night

                                                                    £553 / week

                                                                    Book View

                                                                    from £71 / night

                                                                    Distance approx 18.9 miles from Gaiole in Chianti

                                                                    (23) Excellent 

                                                                      7

                                                                      Holiday apartment in Rosia

                                                                      Province of Siena / Rosia

                                                                      1 4 1 night min

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

                                                                      from £75 / night

                                                                      £412 / week

                                                                      Book View

                                                                      from £75 / night

                                                                      Distance approx 4.59 miles from Gaiole in Chianti Show on Map

                                                                      (1) Excellent 

                                                                        18

                                                                        Holiday farmhouse in Radda in Chianti

                                                                        Province of Siena / Radda in Chianti

                                                                        3 7 3 nights min

                                                                        • 3 bedrooms
                                                                        • sleeps 7
                                                                        • 3 nights min
                                                                        • Child friendly
                                                                        • Pet friendly
                                                                        • Private garden

                                                                        from £151 / night

                                                                        £804 / week

                                                                        Book View

                                                                        from £151 / night

                                                                        Distance approx 13.16 miles from Gaiole in Chianti

                                                                        (4) Excellent 

                                                                          14

                                                                          Holiday apartment in Greve in Chianti

                                                                          Province of Florence / Greve in Chianti

                                                                          2 4 min stay varies

                                                                          • 2 bedrooms
                                                                          • sleeps 4
                                                                          • min stay varies
                                                                          • Child friendly
                                                                          • Air conditioning
                                                                          • Ask about pets

                                                                          Pricing unknown

                                                                          Book View

                                                                          Pricing unknown

                                                                          Distance approx 15.96 miles from Gaiole in Chianti

                                                                            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 £990 / night

                                                                            £6,931 - £8,246 / week

                                                                            Enquire View

                                                                            from £990 / night

                                                                            Distance approx 8.3 miles from Gaiole in Chianti Show on Map

                                                                            (8) Excellent 

                                                                            Certificate of Excellence

                                                                              65

                                                                              Holiday apartment with shared pool in Lucolena

                                                                              Greve in Chianti / Lucolena

                                                                              2 4 min stay varies

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

                                                                              Certificate of Excellence

                                                                              from £101 / night

                                                                              £553 - £1,206 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 2 hours 0 minutes

                                                                              from £101 / night

                                                                              Distance approx 18.08 miles from Gaiole in Chianti

                                                                                17

                                                                                Holiday farmhouse with shared pool in Colle di Val d'Elsa

                                                                                Province of Siena / Colle di Val d'Elsa

                                                                                1 4 min stay varies

                                                                                • 1 bedroom
                                                                                • sleeps 4
                                                                                • min stay varies
                                                                                • Swimming pool
                                                                                • Child friendly
                                                                                • Pet friendly

                                                                                Pricing unknown

                                                                                Book View

                                                                                Pricing unknown

                                                                                Distance approx 13.11 miles from Gaiole in Chianti

                                                                                  24

                                                                                  Holiday farmhouse rental

                                                                                  Province of Siena / Monteriggioni

                                                                                  2 8 3 nights min

                                                                                  • 2 bedrooms
                                                                                  • sleeps 8
                                                                                  • 3 nights min
                                                                                  • Nearest beach 80 km
                                                                                  • Child friendly
                                                                                  • Pet friendly

                                                                                  from £66 / night

                                                                                  £457 / week

                                                                                  Book View

                                                                                  from £66 / night

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