Villas in Montalcino and Apartments - Holiday Lettings - Holiday Rentals Montalcino

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2,204 Holiday homes

(11) Excellent 

    39

    Holiday villa rental

    Montalcino / San Giovanni d'Asso

    8 16 min stay varies

    • 8 bedrooms
    • sleeps 16
    • min stay varies
    • Nearest beach 120 km
    • Swimming pool
    • Child friendly

    from £619 / night

    £4,335 - £5,517 / week

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    Responds fast!
    avg. 3 hours 14 minutes

    from £619 / night

    (4) Excellent 

      8

      Castelnuovo dell'Abate holiday apartment rental

      Montalcino / Castelnuovo dell'Abate

      1 4 1 night min

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

      from £85 / night

      £591 / week

      Book View

      from £85 / night

      (1) Excellent 

        18

        Holiday villa with shared pool in Val d'Orcia

        Montalcino / Val d'Orcia

        2 6 min stay varies

        • 2 bedrooms
        • sleeps 6
        • min stay varies
        • Nearest beach 25 km
        • Swimming pool
        • Child friendly

        from £99 / night

        £636 - £1,325 / week

        Book View

        Responds fast!
        avg. 2 hours 19 minutes

        from £99 / night

        (5) Excellent 

          18

          Holiday home in Castelnuovo dell'Abate

          Montalcino / Castelnuovo dell'Abate

          2 4 1 night min

          • 2 bedrooms
          • sleeps 4
          • 1 night min
          • Nearest beach 50 km
          • Child friendly

          from £128 / night

          £897 / week

          Book View

          from £128 / night

          (14) Excellent 

            20

            Holiday apartment with golf nearby in Sant'Angelo in Colle

            Montalcino / Sant'Angelo in Colle

            2 4 min stay varies

            • 2 bedrooms
            • sleeps 4
            • min stay varies
            • Nearest beach 68 km
            • Child friendly
            • Private garden

            from £74 / night

            £463 - £808 / week

            Book View

            from £74 / night

            (1) Excellent 

              45

              Montalcino holiday farmhouse accommodation

              Province of Siena / Montalcino

              3 8 3 nights min

              • 3 bedrooms
              • sleeps 8
              • 3 nights min
              • Swimming pool
              • Child friendly
              • Pet friendly

              from £325 / night

              £2,276 / week

              Book View

              from £325 / night

              (2) Excellent 

                17

                Holiday farmhouse in San Giovanni d'Asso

                Montalcino / San Giovanni d'Asso

                2 4 5 nights min

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

                from £138 / night

                £690 / week

                Book View

                Responds fast!
                avg. 3 hours 26 minutes

                from £138 / night

                  27

                  Villa rental in Poggio alle Mura with swimming pool

                  Montalcino / Poggio alle Mura

                  5 10 7 nights min

                  • 5 bedrooms
                  • sleeps 10
                  • 7 nights min
                  • Nearest beach 66 km
                  • Swimming pool

                  from £817 / night

                  £5,717 - £9,405 / week

                  Book View

                  from £817 / night

                  (31) Excellent 

                    26

                    Holiday farmhouse with swimming pool in Val d'Orcia

                    Montalcino / Val d'Orcia

                    2 5 2 nights min

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

                    from £119 / night

                    £828 / week

                    Book View

                    from £119 / night

                      4

                      Apartment rental in Montalcino

                      Province of Siena / Montalcino

                      1 2 2 nights min

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

                      from £95 / night

                      £660 / week

                      Book View

                      from £95 / night

                        12

                        Montalcino holiday b&b rental

                        Province of Siena / Montalcino

                        1 3 1 night min

                        • 1 bedroom
                        • sleeps 3
                        • 1 night min

                        from £159 / night

                        £1,112 / week

                        Book View

                        from £159 / night

                        (4) Excellent 

                          21

                          Holiday villa in Montalcino

                          Province of Siena / Montalcino

                          6 12 2 nights min

                          • 6 bedrooms
                          • sleeps 12
                          • 2 nights min
                          • Child friendly

                          from £500 / night

                          £3,498 / week

                          Book View

                          from £500 / night

                          (5) Very Good 

                            40

                            Holiday farmhouse in Montalcino

                            Province of Siena / Montalcino

                            7 14 1 night min

                            • 7 bedrooms
                            • sleeps 14
                            • 1 night min
                            • Nearest beach 65 km
                            • Swimming pool
                            • Child friendly

                            from £119 / night

                            £834 / week

                            Book View

                            from £119 / night

                            (6) Excellent 

                              51

                              Holiday villa with swimming pool in Montalcino

                              Province of Siena / Montalcino

                              4 11 min stay varies

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

                              from £466 / night

                              £3,258 / week

                              Book View

                              from £466 / night

                                33

                                Montalcino holiday villa rental

                                Province of Siena / Montalcino

                                2 5 2 nights min

                                • 2 bedrooms
                                • sleeps 5
                                • 2 nights min
                                • Nearest beach 60 km
                                • Swimming pool
                                • Child friendly

                                from £197 / night

                                £1,380 / week

                                Book View

                                from £197 / night

                                  23

                                  San Giovanni d'Asso holiday home rental

                                  Montalcino / San Giovanni d'Asso

                                  3 6 3 nights min

                                  • 3 bedrooms
                                  • sleeps 6
                                  • 3 nights min
                                  • Nearest beach 90 km
                                  • Swimming pool
                                  • Child friendly

                                  from £128 / night

                                  £739 / week

                                  Book View

                                  from £128 / night

                                  (1) Excellent 

                                    6

                                    Holiday b&b accommodation

                                    Province of Siena / Montalcino

                                    1 2 1 night min

                                    • 1 bedroom
                                    • sleeps 2
                                    • 1 night min
                                    • Child friendly

                                    from £60 / night

                                    £414 / week

                                    Book View

                                    Responds fast!
                                    avg. 2 hours 36 minutes

                                    from £60 / night

                                      50

                                      Holiday apartment in Montalcino

                                      Province of Siena / Montalcino

                                      3 6 3 nights min

                                      • 3 bedrooms
                                      • sleeps 6
                                      • 3 nights min
                                      • Suitable for children age 5+

                                      from £349 / night

                                      £2,442 / week

                                      Book View

                                      from £349 / night

                                        20

                                        Holiday farmhouse in San Giovanni d'Asso

                                        Montalcino / San Giovanni d'Asso

                                        4 8 7 nights min

                                        • 4 bedrooms
                                        • sleeps 8
                                        • 7 nights min
                                        • Nearest beach 90 km
                                        • Swimming pool
                                        • Child friendly

                                        from £189 / night

                                        £1,323 / week

                                        Book View

                                        from £189 / night

                                          24

                                          Holiday apartment in Val d'Orcia

                                          Montalcino / Val d'Orcia

                                          2 6 1 night min

                                          • 2 bedrooms
                                          • sleeps 6
                                          • 1 night min
                                          • Child friendly
                                          • Air conditioning
                                          • Private garden

                                          from £229 / night

                                          £1,598 / week

                                          Book View

                                          from £229 / night

                                          (12) Excellent 

                                            39

                                            Holiday villa with swimming pool in San Giovanni d'Asso

                                            Montalcino / San Giovanni d'Asso

                                            3 5 3 nights min

                                            • 3 bedrooms
                                            • sleeps 5
                                            • 3 nights min
                                            • Nearest beach 120 km
                                            • Swimming pool
                                            • Child friendly

                                            from £268 / night

                                            £1,873 - £2,694 / week

                                            Book View

                                            Responds fast!
                                            avg. 3 hours 14 minutes

                                            from £268 / night

                                              8

                                              Castelnuovo dell'Abate holiday home rental

                                              Montalcino / Castelnuovo dell'Abate

                                              3 7 2 nights min

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

                                              from £196 / night

                                              £1,274 / week

                                              Book View

                                              from £196 / night

                                              (3) Excellent 

                                                37

                                                Holiday villa with swimming pool in San Giovanni d'Asso

                                                Montalcino / San Giovanni d'Asso

                                                3 6 3 nights min

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

                                                from £307 / night

                                                £2,149 - £2,873 / week

                                                Book View

                                                Responds fast!
                                                avg. 3 hours 14 minutes

                                                from £307 / night

                                                  12

                                                  Holiday b&b rental

                                                  Montalcino / Val d'Orcia

                                                  1 2 2 nights min

                                                  • 1 bedroom
                                                  • sleeps 2
                                                  • 2 nights min
                                                  • Nearest beach 80 km
                                                  • Swimming pool
                                                  • Child friendly

                                                  from £119 / night

                                                  £794 / week

                                                  Book View

                                                  from £119 / night

                                                  (3) Excellent 

                                                    15

                                                    Holiday farmhouse in San Giovanni d'Asso

                                                    Montalcino / San Giovanni d'Asso

                                                    2 4 5 nights min

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

                                                    from £118 / night

                                                    £735 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 3 hours 26 minutes

                                                    from £118 / night

                                                      15

                                                      Val d'Orcia holiday apartment rental

                                                      Montalcino / Val d'Orcia

                                                      1 2 3 nights min

                                                      • 1 bedroom
                                                      • sleeps 2
                                                      • 3 nights min
                                                      • Nearest beach 80 km

                                                      from £98 / night

                                                      £686 / week

                                                      Book View

                                                      from £98 / night

                                                        16

                                                        Montalcino holiday apartment rental

                                                        Province of Siena / Montalcino

                                                        2 6 2 nights min

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

                                                        from £373 / night

                                                        £2,449 / week

                                                        Book View

                                                        from £373 / night

                                                          24

                                                          Holiday home in Montalcino

                                                          Province of Siena / Montalcino

                                                          2 5 1 night min

                                                          • 2 bedrooms
                                                          • sleeps 5
                                                          • 1 night min
                                                          • Child friendly
                                                          • Pet friendly

                                                          from £98 / night

                                                          £686 / week

                                                          Book View

                                                          from £98 / night

                                                            15

                                                            Holiday b&b in Val d'Orcia

                                                            Montalcino / Val d'Orcia

                                                            2 4 3 nights min

                                                            • 2 bedrooms
                                                            • sleeps 4
                                                            • 3 nights min
                                                            • Nearest beach 80 km

                                                            from £89 / night

                                                            £618 / week

                                                            Book View

                                                            from £89 / night

                                                              12

                                                              Montalcino holiday b&b rental

                                                              Province of Siena / Montalcino

                                                              1 1 1 night min

                                                              • 1 bedroom
                                                              • sleeps 1
                                                              • 1 night min

                                                              from £75 / night

                                                              £521 / week

                                                              Book View

                                                              from £75 / night

                                                                15

                                                                Apartment rental in Montalcino with shared pool

                                                                Province of Siena / Montalcino

                                                                2 4 2 nights min

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

                                                                from £270 / night

                                                                £1,764 / week

                                                                Book View

                                                                from £270 / night

                                                                  12

                                                                  B&b rental in Montalcino

                                                                  Province of Siena / Montalcino

                                                                  1 2 1 night min

                                                                  • 1 bedroom
                                                                  • sleeps 2
                                                                  • 1 night min

                                                                  from £119 / night

                                                                  £794 / week

                                                                  Book View

                                                                  from £119 / night

                                                                  (7) Excellent 

                                                                    47

                                                                    Holiday villa in Montalcino

                                                                    Province of Siena / Montalcino

                                                                    9 18 7 nights min

                                                                    • 9 bedrooms
                                                                    • sleeps 18
                                                                    • 7 nights min
                                                                    • Swimming pool
                                                                    • Child friendly
                                                                    • Private garden

                                                                    from £524 / night

                                                                    £3,669 - £7,340 / week

                                                                    Book View

                                                                    from £524 / night

                                                                      26

                                                                      Home rental in San Giovanni d'Asso with shared pool

                                                                      Montalcino / San Giovanni d'Asso

                                                                      3 8 3 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 8
                                                                      • 3 nights min
                                                                      • Nearest beach 90 km
                                                                      • Swimming pool
                                                                      • Child friendly

                                                                      from £138 / night

                                                                      £828 / week

                                                                      Book View

                                                                      from £138 / night

                                                                        12

                                                                        B&b rental in Montalcino

                                                                        Province of Siena / Montalcino

                                                                        1 2 1 night min

                                                                        • 1 bedroom
                                                                        • sleeps 2
                                                                        • 1 night min

                                                                        from £119 / night

                                                                        £788 / week

                                                                        Book View

                                                                        from £119 / night

                                                                          51

                                                                          Holiday villa with swimming pool in Poggio alle Mura

                                                                          Montalcino / Poggio alle Mura

                                                                          5 10 7 nights min

                                                                          • 5 bedrooms
                                                                          • sleeps 10
                                                                          • 7 nights min
                                                                          • Nearest beach 66 km
                                                                          • Swimming pool
                                                                          • Child friendly

                                                                          from £664 / night

                                                                          £4,641 - £7,722 / week

                                                                          Book View

                                                                          from £664 / night

                                                                          (1) Very Good 

                                                                            29

                                                                            Villa rental in Castelnuovo dell'Abate with swimming pool

                                                                            Montalcino / Castelnuovo dell'Abate

                                                                            5 8 min stay varies

                                                                            • 5 bedrooms
                                                                            • sleeps 8
                                                                            • min stay varies
                                                                            • Nearest beach 90 km
                                                                            • Swimming pool
                                                                            • Child friendly

                                                                            from £1,162 / night

                                                                            £5,027 / week

                                                                            Enquire View

                                                                            from £1,162 / night

                                                                            (14) Excellent 

                                                                              46

                                                                              Holiday villa in San Giovanni d'Asso

                                                                              Montalcino / San Giovanni d'Asso

                                                                              5 10 min stay varies

                                                                              • 5 bedrooms
                                                                              • sleeps 10
                                                                              • min stay varies
                                                                              • Nearest beach 120 km
                                                                              • Swimming pool
                                                                              • Child friendly

                                                                              from £471 / night

                                                                              £3,292 - £4,311 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 3 hours 14 minutes

                                                                              from £471 / night

                                                                                24

                                                                                Holiday apartment in Val d'Orcia

                                                                                Montalcino / Val d'Orcia

                                                                                1 4 1 night min

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

                                                                                from £199 / night

                                                                                £1,390 / week

                                                                                Book View

                                                                                from £199 / night

                                                                                  24

                                                                                  Holiday home in San Giovanni d'Asso

                                                                                  Montalcino / San Giovanni d'Asso

                                                                                  2 6 min stay varies

                                                                                  • 2 bedrooms
                                                                                  • sleeps 6
                                                                                  • min stay varies
                                                                                  • Nearest beach 150 km
                                                                                  • Child friendly
                                                                                  • Ask about pets

                                                                                  Pricing unknown

                                                                                  Book View

                                                                                  Pricing unknown

                                                                                  Top Destination reviews

                                                                                  Podere Ferranino Townhouses- Cimabue
                                                                                  Beautifully designed and equipped townhouse in a stunning setting.

                                                                                  Four of us had a fantastic stay at Cimabue and were sorry to leave. The converted coach house is excellently laid out and equipped - including washing machine, micro, toaster, coffee maker, air-conditioning and high speed broadband. The grounds are beautiful and the views across the valley are utterly stunning. We were also very pleasantly surprised by the size of the pool and the fact that it had an adjacent jacuzzi. There are some lovely walks in the vicinity. If you like to run off road or to cycle the terrain and available routes in the locality are terrific. We followed the recommendations for restaurants given by our hosts and were not disappointed. We also tried another restaurant in nearby Trequanda. All the restaurants were excellent and very good value. Patricia was a wonderful host - nothing was too much trouble. We won't hesitate to return if we get the chance!see more
                                                                                  Bright and beautiful 4 bedroom Tuscan villa with pool, private garden and barbecue, sleeps 8
                                                                                  Great location, fits all types of travellers specially family reunions

                                                                                  The Villa is placed in a very special and beautiful area in the Tuscany region. Near (up to 1h - 1.20h) many special places and famous cities, such as Siena and Montalcino. The access to the Vila is by a not paved road, and be carefull to enter the road from Torrenieri. The house is great, comfortable and has many facilities. All new and beautiful. I really recommend this house and the hospitality we have received.see more
                                                                                  5BDR Casale ,view on the Crete Senesi,walking to a village,private pool,WiFi
                                                                                  Gorgeous villa in Tuscany

                                                                                  This is a gorgeous villa in the tuscan countryside. The villa was beautiful, spotless and had everything we needed. It is right next to the small town of San Giovanni D'Osso. My 16-year-old loved it as well. While we day-tripped to surrounding towns including Sienna and Florence, we always enjoyed coming back to the villa to swim and prepare dinner. I can't wait for the next time when we can return there with our friends. Great hosts as well.see more
                                                                                  8BDR Historic villa in the Crete Senesi walking to a village : view,pool,garden
                                                                                  unforgettable tuscan paradise

                                                                                  Wonderful historic house, charming atmosphere, you feel at home. We were a group of 16 friends, the house was perfect, nothing was missing. Nice accommodations very clean, housekeeping every day. Unforgettable breakfast on the terrace in front of the scenic, lunch in the beautiful garden and dinner by the cooker (so delicious!!) Federica, the owner , and all the staff are kind and helpful. If you need an address, do not hesitate to ask her, especially for tasting Brunello. One of the best places toto stay for visiting and appreciating Tuscany!see more
                                                                                  3BDR Casale Il Tribbio Il ,view on the Crete ,close to a village
                                                                                  Perfect.

                                                                                  The owner was most helpful in terms of booking, meeting us, and checking in to ensure all was going well. We took advantage of her offer to arrange for a chef to cook for us our first night - delicious food and very good wines. If you arrive on a Saturday, have them bring in some groceries - everything is shut up tight on Sunday. The villa itself is lovely, the views spectacular and location convenient for touring. The highlight at the end of each day was returning to the pool and quiet evenings outside.see more
                                                                                  Fonte Aulente Montalcino
                                                                                  Great Location

                                                                                  We can only reiterate the excellent reviews that have gone before. Fonte Aulente is in a great location, quiet and secluded with amazing views of the Tuscan countryside and close to the beautiful town of Montalcino. The accommodation, including the extensive garden with its large fresh water pool, offered everything our family of four needed. We were close enough to visit Siena, Florence, Pisa and the beach on day trips. Our hostess Alexandra was welcoming and helpful throughout the stay without ever being intrusive, suggesting local drives and sharing her passion for the local wines. We thoroughly enjoyed our two week stay at Fonte Aulente and look forward to returning in the future.see more

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