Gaiole in Chianti Holidays & City Breaks - Holiday Lettings

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Filters applied: City breaks

633 properties suitable for city breaks and holidays

(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

    £1,455 - £2,424 / week

    Book View

    Responds fast!
    avg. 3 hours 56 minutes

    from £207 / 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 £527 / night

      £3,466 - £5,666 / week

      Book View

      Responds fast!
      avg. 3 hours 56 minutes

      from £527 / 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

        £505 - £5,878 / week

        Book View

        from £77 / night

        (3) Very Good 

          33

          Holiday villa with shared pool in Gaiole in Chianti

          Province of Siena / Gaiole in Chianti

          3 8 7 nights min

          • 3 bedrooms
          • sleeps 8
          • 7 nights min
          • Nearest beach 107 km
          • Swimming pool
          • Child friendly

          from £95 / night

          £661 - £1,326 / week

          Enquire View

          from £95 / night

            11

            Gaiole in Chianti holiday apartment rental

            Province of Siena / Gaiole in Chianti

            3 5 1 night min

            • 3 bedrooms
            • sleeps 5
            • 1 night min
            • Swimming pool
            • Child friendly
            • Pet friendly

            from £222 / night

            £1,362 / week

            Book View

            from £222 / 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 £607 / night

              £4,245 / week

              Book View

              from £607 / night

                8

                Holiday apartment in Gaiole in Chianti

                Province of Siena / Gaiole in Chianti

                1 4 3 nights min

                • 1 bedroom
                • sleeps 4
                • 3 nights min
                • Child friendly

                from £91 / night

                £635 / week

                Book View

                from £91 / night

                  8

                  Holiday apartment in Gaiole in Chianti

                  Province of Siena / Gaiole in Chianti

                  1 4 3 nights min

                  • 1 bedroom
                  • sleeps 4
                  • 3 nights min
                  • Child friendly

                  from £91 / night

                  £633 / week

                  Book View

                  from £91 / night

                  Great rentals within 20 miles that match your search

                  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 9.08 miles from Gaiole in Chianti Show on Map

                    (13) Excellent 

                      17

                      Holiday apartment rental

                      Province of Arezzo / Ambra

                      2 4 7 nights min

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

                      from £79 / night

                      £549 / week

                      Book View

                      from £79 / night

                      Distance approx 17.05 miles from Gaiole in Chianti

                      (3) Excellent 

                        21

                        Home rental in Impruneta

                        Province of Florence / Impruneta

                        2 6 min stay varies

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

                        from £111 / night

                        £704 / week

                        Book View

                        from £111 / night

                        Distance approx 4.17 miles from Gaiole in Chianti Show on Map

                        (1) Excellent 

                          55

                          Holiday villa with swimming pool, golf nearby in Cavriglia

                          Province of Arezzo / Cavriglia

                          4 8 7 nights min

                          • 4 bedrooms
                          • sleeps 8
                          • 7 nights min
                          • Swimming pool
                          • Child friendly
                          • Pet friendly

                          from £234 / night

                          £1,638 - £2,612 / week

                          Book View

                          from £234 / night

                          Distance approx 4.79 miles from Gaiole in Chianti Show on Map

                          (28) Excellent 

                            122

                            Tuscany holiday villa rental

                            Tuscany

                            7 16 7 nights min

                            • 7 bedrooms
                            • sleeps 16
                            • 7 nights min
                            • Nearest beach 140 km
                            • Swimming pool
                            • Child friendly

                            from £1,596 / night

                            £11,172 / week

                            Book View

                            from £1,596 / night

                            Distance approx 4.44 miles from Gaiole in Chianti Show on Map

                              35

                              Holiday apartment in Moncioni

                              Montevarchi / Moncioni

                              1 2 3 nights min

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

                              from £91 / night

                              £593 / week

                              Book View

                              from £91 / night

                              Distance approx 19.8 miles from Gaiole in Chianti

                              (17) Excellent 

                                35

                                Villa rental in Bagno a Ripoli

                                Province of Florence / Bagno a Ripoli

                                3 8 2 nights min

                                • 3 bedrooms
                                • sleeps 8
                                • 2 nights min
                                • Nearest beach 50 km
                                • Child friendly
                                • Air conditioning

                                from £161 / night

                                £916 - £1,374 / week

                                Book View

                                Responds fast!
                                avg. 50 minutes

                                from £161 / night

                                Distance approx 12.21 miles from Gaiole in Chianti

                                (5) Excellent 

                                  47

                                  Loro Ciuffenna holiday b&b rental

                                  Province of Arezzo / Loro Ciuffenna

                                  1 3 1 night min

                                  • 1 bedroom
                                  • sleeps 3
                                  • 1 night min
                                  • Nearest beach 130 km
                                  • Child friendly
                                  • Private garden

                                  from £63 / night

                                  £392 - £462 / week

                                  Book View

                                  from £63 / night

                                  Distance approx 13.1 miles from Gaiole in Chianti

                                    6

                                    Holiday b&b in Greve in Chianti

                                    Province of Florence / Greve in Chianti

                                    6 17 1 night min

                                    • 6 bedrooms
                                    • sleeps 17
                                    • 1 night min
                                    • Air conditioning

                                    from £81 / night

                                    £562 / week

                                    Book View

                                    Responds fast!
                                    avg. 34 minutes

                                    from £81 / night

                                    Distance approx 5.56 miles from Gaiole in Chianti Show on Map

                                      14

                                      Holiday apartment accommodation

                                      Province of Arezzo / Montevarchi

                                      1 2 min stay varies

                                      • 1 bedroom
                                      • sleeps 2
                                      • min stay varies
                                      • Air conditioning
                                      • Ask about pets
                                      • Private garden

                                      Pricing unknown

                                      Book View

                                      Pricing unknown

                                      Distance approx 6.55 miles from Gaiole in Chianti Show on Map

                                        11

                                        Holiday farmhouse with shared pool in San Giovanni Valdarno

                                        Province of Arezzo / San Giovanni Valdarno

                                        4 4 min stay varies

                                        • 4 bedrooms
                                        • sleeps 4
                                        • min stay varies
                                        • Swimming pool
                                        • Child friendly
                                        • Car not necessary

                                        Pricing unknown

                                        Book View

                                        Pricing unknown

                                        Distance approx 15.57 miles from Gaiole in Chianti

                                        (3) Excellent 

                                          20

                                          Holiday villa with shared pool in Mercatale di Val di Pesa

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

                                          5 10 7 nights min

                                          • 5 bedrooms
                                          • sleeps 10
                                          • 7 nights min
                                          • Swimming pool
                                          • Child friendly
                                          • Air conditioning

                                          from £1,434 / night

                                          £10,038 / week

                                          Book View

                                          from £1,434 / night

                                          Distance approx 17.87 miles from Gaiole in Chianti

                                            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

                                            £844 - £1,054 / week

                                            Book View

                                            from £121 / night

                                            Distance approx 12.7 miles from Gaiole in Chianti

                                            (6) Excellent 

                                              32

                                              Castelfranco di Sopra holiday cottage rental

                                              Castelfranco Piandisco / Castelfranco di Sopra

                                              2 4 1 night min

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

                                              from £126 / night

                                              £864 / week

                                              Book View

                                              Responds fast!
                                              avg. 1 hour 31 minutes

                                              from £126 / night

                                              Distance approx 17.82 miles from Gaiole in Chianti

                                              (2) Excellent 

                                                22

                                                Holiday apartment with shared pool in Monte San Savino

                                                Province of Arezzo / Monte San Savino

                                                2 6 1 night min

                                                • 2 bedrooms
                                                • sleeps 6
                                                • 1 night min
                                                • Nearest beach 140 km
                                                • Swimming pool
                                                • Child friendly

                                                from £151 / night

                                                £1,054 / week

                                                Book View

                                                from £151 / night

                                                Distance approx 18.93 miles from Gaiole in Chianti

                                                (2) Very Good 

                                                  12

                                                  Holiday farmhouse letting

                                                  Province of Siena / San Gimignano

                                                  1 2 3 nights min

                                                  • 1 bedroom
                                                  • sleeps 2
                                                  • 3 nights min
                                                  • Beach / lakeside relaxation
                                                  • Nearest beach 80 km
                                                  • Swimming pool

                                                  from £91 / night

                                                  £603 / week

                                                  Book View

                                                  from £91 / night

                                                  Distance approx 17.54 miles from Gaiole in Chianti

                                                  (11) Excellent 

                                                    14

                                                    Holiday farmhouse with shared pool in Rignano sull'Arno

                                                    Province of Florence / Rignano sull'Arno

                                                    2 6 min stay varies

                                                    • 2 bedrooms
                                                    • sleeps 6
                                                    • min stay varies
                                                    • Nearest beach 60 km
                                                    • Swimming pool
                                                    • Child friendly

                                                    Pricing unknown

                                                    Book View

                                                    Pricing unknown

                                                    Distance approx 12.02 miles from Gaiole in Chianti

                                                    (1) Excellent 

                                                      11

                                                      Holiday farmhouse with shared pool in Cicogna

                                                      Province of Arezzo / Cicogna

                                                      2 7 min stay varies

                                                      • 2 bedrooms
                                                      • sleeps 7
                                                      • min stay varies
                                                      • Swimming pool
                                                      • Child friendly
                                                      • Air conditioning

                                                      from £186 / night

                                                      £1,275 / week

                                                      Book View

                                                      from £186 / night

                                                      Distance approx 4.47 miles from Gaiole in Chianti Show on Map

                                                        45

                                                        Holiday apartment in Moncioni

                                                        Montevarchi / Moncioni

                                                        1 4 1 night min

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

                                                        from £121 / night

                                                        £793 / week

                                                        Book View

                                                        from £121 / night

                                                        Distance approx 3.46 miles from Gaiole in Chianti Show on Map

                                                        (3) Excellent 

                                                          30

                                                          Holiday farmhouse rental

                                                          Province of Arezzo / Montevarchi

                                                          1 3 min stay varies

                                                          • 1 bedroom
                                                          • sleeps 3
                                                          • min stay varies
                                                          • Nearest beach 130 km
                                                          • Swimming pool
                                                          • Child friendly

                                                          from £81 / night

                                                          £558 - £885 / week

                                                          Book View

                                                          from £81 / night

                                                          Distance approx 18.28 miles from Gaiole in Chianti

                                                          (1) Excellent 

                                                            41

                                                            Holiday apartment with shared pool in Lucardo

                                                            Montespertoli / Lucardo

                                                            3 7 2 nights min

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

                                                            from £206 / night

                                                            £995 / week

                                                            Book View

                                                            from £206 / night

                                                            Distance approx 18.69 miles from Gaiole in Chianti

                                                            (25) Excellent 

                                                              19

                                                              Apartment rental in San Gimignano

                                                              Province of Siena / San Gimignano

                                                              1 3 3 nights min

                                                              • 1 bedroom
                                                              • sleeps 3
                                                              • 3 nights min
                                                              • Nearest beach 72 km
                                                              • Child friendly
                                                              • Private garden

                                                              from £66 / night

                                                              £402 - £453 / week

                                                              Book View

                                                              Responds fast!
                                                              avg. 3 hours 7 minutes

                                                              from £66 / night

                                                              Distance approx 15.61 miles from Gaiole in Chianti

                                                              (1) Excellent 

                                                                18

                                                                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
                                                                • Car not necessary

                                                                from £1,434 / night

                                                                £10,038 / week

                                                                Book View

                                                                from £1,434 / night

                                                                Distance approx 4.86 miles from Gaiole in Chianti Show on Map

                                                                (3) Excellent 

                                                                  33

                                                                  Holiday home letting

                                                                  Castelnuovo Berardenga / San Gusme

                                                                  3 8 7 nights min

                                                                  • 3 bedrooms
                                                                  • sleeps 8
                                                                  • 7 nights min
                                                                  • Child friendly
                                                                  • Pet friendly

                                                                  from £249 / night

                                                                  £1,738 / week

                                                                  Book View

                                                                  from £249 / night

                                                                  Distance approx 17.94 miles from Gaiole in Chianti

                                                                    62

                                                                    Villa rental in Rignano sull'Arno with swimming pool

                                                                    Province of Florence / Rignano sull'Arno

                                                                    8 15 7 nights min

                                                                    • 8 bedrooms
                                                                    • sleeps 15
                                                                    • 7 nights min
                                                                    • Nearest beach 134 km
                                                                    • Swimming pool
                                                                    • Ask owner if suitable for children

                                                                    from £486 / night

                                                                    £3,399 - £5,922 / week

                                                                    Book View

                                                                    from £486 / night

                                                                    Distance approx 12.73 miles from Gaiole in Chianti

                                                                    (20) Excellent 

                                                                      19

                                                                      Holiday apartment in Poggio alla Croce

                                                                      Greve in Chianti / Poggio alla Croce

                                                                      2 5 3 nights min

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

                                                                      from £81 / night

                                                                      £473 - £513 / week

                                                                      Book View

                                                                      Responds fast!
                                                                      avg. 3 hours 0 minutes

                                                                      from £81 / night

                                                                      Distance approx 11.89 miles from Gaiole in Chianti Show on Map

                                                                        28

                                                                        B&b rental in Siena

                                                                        Province of Siena / Siena

                                                                        1 1 1 night min

                                                                        • 1 bedroom
                                                                        • sleeps 1
                                                                        • 1 night min
                                                                        • Nearest beach 80 km

                                                                        from £50 / night

                                                                        £282 / week

                                                                        Book View

                                                                        from £50 / night

                                                                        Distance approx 18.93 miles from Gaiole in Chianti

                                                                        (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 £409 / night

                                                                          £2,864 / week

                                                                          Book View

                                                                          from £409 / night

                                                                          Distance approx 6.92 miles from Gaiole in Chianti Show on Map

                                                                            18

                                                                            Apartment rental in Castellina In Chianti with shared pool

                                                                            Province of Siena / Castellina In Chianti

                                                                            2 5 1 night min

                                                                            • 2 bedrooms
                                                                            • sleeps 5
                                                                            • 1 night min
                                                                            • Swimming pool
                                                                            • Child friendly
                                                                            • Air conditioning

                                                                            from £252 / night

                                                                            £1,759 / week

                                                                            Book View

                                                                            from £252 / night

                                                                            Distance approx 19.24 miles from Gaiole in Chianti

                                                                              48

                                                                              Holiday home rental

                                                                              Sinalunga / Rigomagno

                                                                              5 10 min stay varies

                                                                              • 5 bedrooms
                                                                              • sleeps 10
                                                                              • min stay varies
                                                                              • Swimming pool
                                                                              • Child friendly
                                                                              • Private garden

                                                                              from £255 / night

                                                                              £1,668 - £2,194 / week

                                                                              Book View

                                                                              from £255 / night

                                                                              Distance approx 13.75 miles from Gaiole in Chianti

                                                                                43

                                                                                Loro Ciuffenna holiday finca rental

                                                                                Province of Arezzo / Loro Ciuffenna

                                                                                5 12 4 nights min

                                                                                • 5 bedrooms
                                                                                • sleeps 12
                                                                                • 4 nights min
                                                                                • Swimming pool
                                                                                • Child friendly
                                                                                • Private garden

                                                                                from £151 / night

                                                                                £1,055 / week

                                                                                Book View

                                                                                from £151 / night

                                                                                Distance approx 11.27 miles from Gaiole in Chianti Show on Map

                                                                                  25

                                                                                  Holiday apartment in Siena

                                                                                  Province of Siena / Siena

                                                                                  3 6 min stay varies

                                                                                  • 3 bedrooms
                                                                                  • sleeps 6
                                                                                  • min stay varies
                                                                                  • Child friendly

                                                                                  from £109 / night

                                                                                  £654 - £977 / week

                                                                                  Book View

                                                                                  Responds fast!
                                                                                  avg. 1 hour 32 minutes

                                                                                  from £109 / night

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