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

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4,832 Holiday homes

(1) Excellent 

    18

    Holiday apartment rental

    Province of Siena / Montepulciano

    2 7 1 night min

    • 2 bedrooms
    • sleeps 7
    • 1 night min
    • Child friendly
    • Pet friendly
    • Private garden

    from £62 / night

    £413 - £766 / week

    Book View

    Responds fast!
    avg. 47 minutes

    from £62 / night

    (1) Excellent 

      12

      Holiday home rental

      Province of Siena / Montepulciano

      4 8 1 night min

      • 4 bedrooms
      • sleeps 8
      • 1 night min
      • Child friendly
      • Pet friendly
      • Private garden

      from £353 / night

      £2,468 / week

      Book View

      from £353 / night

      (1) Excellent 

        21

        Holiday townhouse rental

        Province of Siena / Montepulciano

        2 6 1 night min

        • 2 bedrooms
        • sleeps 6
        • 1 night min
        • Suitable for children age 5+

        from £126 / night

        £705 - £987 / week

        Book View

        from £126 / night

        (3) Excellent 

          16

          Montepulciano holiday b&b rental

          Province of Siena / Montepulciano

          6 12 2 nights min

          • 6 bedrooms
          • sleeps 12
          • 2 nights min
          • Beach / lakeside relaxation
          • Swimming pool
          • Child friendly

          from £172 / night

          £1,199 / week

          Book View

          from £172 / night

          (1) Excellent 

            23

            Holiday villa with shared pool in Montepulciano

            Province of Siena / Montepulciano

            4 2 1 night min

            • 4 bedrooms
            • sleeps 2
            • 1 night min
            • Nearest beach 120 km
            • Swimming pool
            • Ask owner if suitable for children

            from £41 / night

            £282 / week

            Book View

            Responds fast!
            avg. 3 hours 19 minutes

            from £41 / night

              11

              Holiday farmhouse rental

              Province of Siena / Montepulciano

              9 18 4 nights min

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

              from £806 / night

              £4,130 / week

              Book View

              Responds fast!
              avg. 2 hours 53 minutes

              from £806 / night

              (14) Excellent 

                19

                Holiday apartment in Montepulciano

                Province of Siena / Montepulciano

                2 4 2 nights min

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

                from £116 / night

                £695 - £1,013 / week

                Book View

                from £116 / night

                (2) Excellent 

                  7

                  Farmhouse rental in Montepulciano with shared pool

                  Province of Siena / Montepulciano

                  4 4 2 nights min

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

                  from £71 / night

                  £423 / week

                  Book View

                  from £71 / night

                    33

                    Holiday apartment rental

                    Province of Siena / Montepulciano

                    2 6 min stay varies

                    • 2 bedrooms
                    • sleeps 6
                    • min stay varies
                    • Nearest beach 115 km
                    • Swimming pool
                    • Child friendly

                    from £103 / night

                    £721 / week

                    Enquire View

                    from £103 / night

                    (1) Excellent 

                      18

                      Farmhouse rental in Montepulciano with shared pool

                      Province of Siena / Montepulciano

                      7 4 3 nights min

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

                      from £116 / night

                      £811 / week

                      Book View

                      from £116 / night

                      (2) Excellent 

                        29

                        Holiday farmhouse in Montepulciano

                        Province of Siena / Montepulciano

                        4 8 3 nights min

                        • 4 bedrooms
                        • sleeps 8
                        • 3 nights min
                        • Child friendly
                        • Air conditioning
                        • Pet friendly

                        from £353 / night

                        £1,914 - £2,619 / week

                        Book View

                        from £353 / night

                          33

                          Montepulciano holiday villa let

                          Province of Siena / Montepulciano

                          7 14 min stay varies

                          • 7 bedrooms
                          • sleeps 14
                          • min stay varies
                          • Swimming pool
                          • Child friendly
                          • Private garden

                          from £192 / night

                          £1,340 - £2,468 / week

                          Book View

                          from £192 / night

                          (1) Excellent 

                            11

                            Montepulciano holiday home rental

                            Province of Siena / Montepulciano

                            2 6 1 night min

                            • 2 bedrooms
                            • sleeps 6
                            • 1 night min
                            • Child friendly
                            • Pet friendly

                            from £101 / night

                            £504 / week

                            Book View

                            from £101 / night

                              34

                              Holiday villa with swimming pool in Montepulciano

                              Province of Siena / Montepulciano

                              7 14 min stay varies

                              • 7 bedrooms
                              • sleeps 14
                              • min stay varies
                              • Nearest beach 150 km
                              • Swimming pool
                              • Child friendly

                              from £705 / night

                              £3,626 - £6,647 / week

                              Book View

                              from £705 / night

                                21

                                Holiday home with shared pool in Montepulciano

                                Province of Siena / Montepulciano

                                1 4 1 night min

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

                                from £110 / night

                                £756 / week

                                Book View

                                from £110 / night

                                (10) Very Good 

                                  41

                                  Holiday farmhouse with shared pool in Montepulciano

                                  Province of Siena / Montepulciano

                                  2 6 7 nights min

                                  • 2 bedrooms
                                  • sleeps 6
                                  • 7 nights min
                                  • Nearest beach 0 km
                                  • Swimming pool
                                  • Child friendly
                                  “A super house, with fabulous open views and a delightful garden and pool area.” The house was spacious even for 6 of us and the location was peaceful. Pool area was fantastic for the children and the sunsets from the patio were gorgeous. Well placed for sightseeing in Sienna, Florence, Lake Trasiemo and lots of other hill top towns.

                                  from £115 / night

                                  £802 - £974 / week

                                  Book View

                                  from £115 / night

                                  (17) Excellent 

                                    34

                                    Holiday home in Montepulciano

                                    Province of Siena / Montepulciano

                                    2 4 2 nights min

                                    • 2 bedrooms
                                    • sleeps 4
                                    • 2 nights min
                                    • Nearest beach 120 km
                                    • Child friendly
                                    • Air conditioning

                                    from £76 / night

                                    £504 - £746 / week

                                    Book View

                                    from £76 / night

                                    (5) Excellent 

                                      24

                                      Holiday farmhouse with swimming pool in Montepulciano

                                      Province of Siena / Montepulciano

                                      5 10 min stay varies

                                      • 5 bedrooms
                                      • sleeps 10
                                      • min stay varies
                                      • Nearest beach 200 km
                                      • Swimming pool
                                      • Child friendly

                                      from £464 / night

                                      £2,417 - £3,928 / week

                                      Book View

                                      from £464 / night

                                      (2) Excellent 

                                        17

                                        Holiday farmhouse in Montepulciano

                                        Province of Siena / Montepulciano

                                        2 4 7 nights min

                                        • 2 bedrooms
                                        • sleeps 4
                                        • 7 nights min
                                        • Nearest beach 106 km
                                        • Child friendly
                                        • Car not necessary

                                        from £144 / night

                                        £1,007 / week

                                        Book View

                                        from £144 / night

                                          7

                                          Holiday apartment with shared pool in Valiano

                                          Montepulciano / Valiano

                                          1 4 3 nights min

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

                                          from £151 / night

                                          £917 / week

                                          Book View

                                          Responds fast!
                                          avg. 2 hours 53 minutes

                                          from £151 / night

                                          (26) Excellent 

                                            24

                                            Holiday apartment in Montepulciano

                                            Province of Siena / Montepulciano

                                            2 6 min stay varies

                                            • 2 bedrooms
                                            • sleeps 6
                                            • min stay varies
                                            • Nearest beach 170 km
                                            • Child friendly
                                            • Car not necessary

                                            from £116 / night

                                            £654 - £1,198 / week

                                            Book View

                                            Responds fast!
                                            avg. 1 hour 55 minutes

                                            from £116 / night

                                            (11) Excellent 

                                              37

                                              Apartment rental in Montepulciano with shared pool

                                              Province of Siena / Montepulciano

                                              2 4 1 night min

                                              • 2 bedrooms
                                              • sleeps 4
                                              • 1 night min
                                              • Nearest beach 120 km
                                              • Swimming pool
                                              • Child friendly

                                              from £51 / night

                                              £353 / week

                                              Book View

                                              Responds fast!
                                              avg. 3 hours 19 minutes

                                              from £51 / night

                                                5

                                                Holiday b&b in Montepulciano

                                                Province of Siena / Montepulciano

                                                1 3 1 night min

                                                • 1 bedroom
                                                • sleeps 3
                                                • 1 night min
                                                • Child friendly

                                                from £101 / night

                                                £705 / week

                                                Book View

                                                from £101 / night

                                                (1) Excellent 

                                                  17

                                                  Holiday apartment with shared pool in Montepulciano

                                                  Province of Siena / Montepulciano

                                                  1 2 min stay varies

                                                  • 1 bedroom
                                                  • sleeps 2
                                                  • min stay varies
                                                  • Swimming pool
                                                  • Child friendly
                                                  • Air conditioning

                                                  from £66 / night

                                                  £373 - £811 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 2 hours 49 minutes

                                                  from £66 / night

                                                    26

                                                    Holiday villa with swimming pool in Montepulciano

                                                    Province of Siena / Montepulciano

                                                    5 10 5 nights min

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

                                                    from £504 / night

                                                    £3,022 / week

                                                    Book View

                                                    from £504 / night

                                                    (56) Excellent 

                                                    Certificate of Excellence

                                                      21

                                                      Holiday cottage in Montepulciano

                                                      Province of Siena / Montepulciano

                                                      3 5 3 nights min

                                                      • 3 bedrooms
                                                      • sleeps 5
                                                      • 3 nights min
                                                      • Nearest beach 158 km
                                                      • Child friendly
                                                      • Air conditioning
                                                      “AWESOME HOUSE!!” We loved this house. It was extremely clean both inside and out. Well decorated and had everything we need during our stay. We fixed breakfast each morning and enjoyed sitting in the garden, admiring the wonderful view. We enjoyed the privacy of the property, yet a short walk into Montepuliciano. We rented a car and drove through the beautiful countryside of Tuscany, visiting several cities. Davide was great to work with, he quickly responded to all my emails, answered all question promptly. The location was perfect to shop, enjoy fabulous restraunts and great wines I highly recommend this house for your stay in Tuscany. I'm sure you'll love it!!

                                                      Certificate of Excellence

                                                      from £71 / night

                                                      £454 - £705 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 2 hours 21 minutes

                                                      from £71 / night

                                                        9

                                                        Holiday apartment with shared pool in Montepulciano

                                                        Province of Siena / Montepulciano

                                                        1 4 2 nights min

                                                        • 1 bedroom
                                                        • sleeps 4
                                                        • 2 nights min
                                                        • Swimming pool
                                                        • Child friendly
                                                        • Pet friendly

                                                        from £111 / night

                                                        £705 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 3 hours 30 minutes

                                                        from £111 / night

                                                          6

                                                          Holiday apartment with shared pool in Montepulciano

                                                          Province of Siena / Montepulciano

                                                          1 2 4 nights min

                                                          • 1 bedroom
                                                          • sleeps 2
                                                          • 4 nights min
                                                          • Swimming pool
                                                          • Child friendly

                                                          from £151 / night

                                                          £756 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 2 hours 53 minutes

                                                          from £151 / night

                                                          (3) Very Good 

                                                            17

                                                            Holiday apartment in Montepulciano

                                                            Province of Siena / Montepulciano

                                                            2 5 4 nights min

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

                                                            from £101 / night

                                                            £600 - £1,164 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 2 hours 4 minutes

                                                            from £101 / night

                                                              8

                                                              Apartment rental in Montepulciano

                                                              Province of Siena / Montepulciano

                                                              3 6 2 nights min

                                                              • 3 bedrooms
                                                              • sleeps 6
                                                              • 2 nights min
                                                              • Private garden

                                                              from £131 / night

                                                              £655 / week

                                                              Book View

                                                              from £131 / night

                                                              (1) Excellent 

                                                                13

                                                                Holiday chalet in Valiano

                                                                Montepulciano / Valiano

                                                                2 4 1 night min

                                                                • 2 bedrooms
                                                                • sleeps 4
                                                                • 1 night min
                                                                • Beach / lakeside relaxation
                                                                • Swimming pool
                                                                • Child friendly

                                                                from £121 / night

                                                                £856 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 2 hours 53 minutes

                                                                from £121 / night

                                                                (5) Very Good 

                                                                  27

                                                                  Apartment rental in Montepulciano with shared pool

                                                                  Province of Siena / Montepulciano

                                                                  2 4 1 night min

                                                                  • 2 bedrooms
                                                                  • sleeps 4
                                                                  • 1 night min
                                                                  • Nearest beach 120 km
                                                                  • Swimming pool
                                                                  • Child friendly

                                                                  from £71 / night

                                                                  £494 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 3 hours 19 minutes

                                                                  from £71 / night

                                                                    21

                                                                    Holiday apartment in Montepulciano

                                                                    Province of Siena / Montepulciano

                                                                    2 5 2 nights min

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

                                                                    from £86 / night

                                                                    £534 - £661 / week

                                                                    Book View

                                                                    from £86 / night

                                                                      10

                                                                      Valiano holiday apartment rental

                                                                      Montepulciano / Valiano

                                                                      1 2 2 nights min

                                                                      • 1 bedroom
                                                                      • sleeps 2
                                                                      • 2 nights min
                                                                      • Swimming pool
                                                                      • Child friendly
                                                                      • Car not necessary

                                                                      from £101 / night

                                                                      £705 / week

                                                                      Book View

                                                                      from £101 / night

                                                                      (5) Excellent 

                                                                        24

                                                                        Montepulciano holiday apartment rental

                                                                        Province of Siena / Montepulciano

                                                                        1 4 3 nights min

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

                                                                        from £79 / night

                                                                        £464 / week

                                                                        Book View

                                                                        from £79 / night

                                                                          5

                                                                          B&b rental in Montepulciano

                                                                          Province of Siena / Montepulciano

                                                                          1 4 1 night min

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

                                                                          from £121 / night

                                                                          £846 / week

                                                                          Book View

                                                                          from £121 / night

                                                                            32

                                                                            Valiano holiday farmhouse rental

                                                                            Montepulciano / Valiano

                                                                            1 2 1 night min

                                                                            • 1 bedroom
                                                                            • sleeps 2
                                                                            • 1 night min
                                                                            • Child friendly
                                                                            • Ask about pets

                                                                            from £81 / night

                                                                            £454 / week

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 37 minutes

                                                                            from £81 / night

                                                                            (17) Excellent 

                                                                              31

                                                                              Holiday apartment in Montepulciano

                                                                              Province of Siena / Montepulciano

                                                                              3 6 2 nights min

                                                                              • 3 bedrooms
                                                                              • sleeps 6
                                                                              • 2 nights min
                                                                              • Child friendly
                                                                              • Car not necessary

                                                                              from £246 / night

                                                                              £1,451 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 51 minutes

                                                                              from £246 / night

                                                                                8

                                                                                Holiday apartment in Valiano

                                                                                Montepulciano / Valiano

                                                                                2 5 4 nights min

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

                                                                                from £202 / night

                                                                                £1,108 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 2 hours 53 minutes

                                                                                from £202 / night

                                                                                (9) Very Good 

                                                                                  6

                                                                                  Valiano holiday home rental

                                                                                  Montepulciano / Valiano

                                                                                  1 2 4 nights min

                                                                                  • 1 bedroom
                                                                                  • sleeps 2
                                                                                  • 4 nights min
                                                                                  • Beach / lakeside relaxation
                                                                                  • Pet friendly

                                                                                  from £51 / night

                                                                                  £303 / week

                                                                                  Book View

                                                                                  from £51 / night

                                                                                  Top Destination reviews

                                                                                  Bibi 5 seater House Montepulciano
                                                                                  A fabulous place to stay

                                                                                  The villa is well situated, within walking distance from the old town. It has beautiful views across the countryside. It was lovely to sit on the terrace in the cool as the sun was setting. We had a wonderful stay, as the villa was very well set up, with everything you need to make your own meals. The beds were comfortable and it was great to have two bathrooms. It was very clean, we were warmly welcomed, and an added surprise was a delicious cake, warm from the oven, made by Silvana. We felt very much at home in your lovely villa. Thank you for a fantastic stay.see more
                                                                                  Charming Cottage in Peaceful Country Setting - Sleeps 6
                                                                                  We will come back!

                                                                                  It was great staying here! We found a nice little place to feel at home. The cottage is lovely furnished, very clean and has everything we needed for the week (including fast heating for some rainy and cold evenings (20minutes was enough to get the humid air out!) and free Wi-Fi, thats working perfectly and fast). We really loved sitting in the beautiful garden full of roses, looking over the wine-yards and listening to all the birds (also nightingales!!!). The cottage is set in a great surrounding - Tuscany like in a picture book! Laura was a perfect host. We felt very welcomed, we could ask her for everything and she could give us good hints for restaurants, hiking-paths and everything else you need to know for holiday. Thank you very much, Laura!see more
                                                                                  La Casina Toscana, central with parking and wi-fi
                                                                                  Clean, comfortable and cozy house with privacy and convenience to Montepuciano

                                                                                  We had a very enjoyable stay at Davide's house. It is a truly charming place offering the privacy you need as a family and at the same time the convenience of being close enough to walk to the Montepulciano town. The place was very clean and thoughtfully renovated. It also has a nice view of the town and the Tuscan landscape. We were there in Dec so were able to make use of the wood-burning fireplace that added to the coziness. The whole rental experience was very pleasant as Davide was extremely responsive and provided helpful information from arrival to departure. We highly recommend the place and would not hesitate to go back again!see more
                                                                                  The Beautiful Sun Apartment
                                                                                  Well maintained apartment and very helpful owner

                                                                                  Elias iwas most helpful meeting us on arrival and going through everything with us and all places to visit in the area even giving us a map with this all marked on The apartment is beautifully kept and everything we needed was there. All to a good standard. The only thing we would say if anything is that we really expected the balcony area to look over the Tuscan hills as from the picture this is what we thought. But it actually looks over a school and onto other buildings.see more
                                                                                  Unique, charming farmhouse in Tuscany countryside with shared outdoor pool, sleeps up to 6
                                                                                  Stunning Views

                                                                                  We had a most enjoyable time at this house and would recommend it for its location and closeness to Montepulciano. The house was delightful and the views across the valley and surrounding countryside were excellent. We can recommend the local farm nearby called the Il Greppo Family Farm. We enjoyed their weekly Saturday evening meal and sent wine home to taste at Christmas. Unfortunately, not long after our arrival, my husband was admitted to the local hospital with bronchial pneumonia and stayed there for 9 nights. The care he received while in hospital was fantastic so we can certainly recommend the local hospital.see more
                                                                                  Villa in Tuscany
                                                                                  Fantastic

                                                                                  A great villa in a great location. Because of a minor error in the booking the owner treated us all to a meal by personal chefs Dorians Ottaviana and Claudio from Cooking for You. They came to the villa and prepared a sumptuous 4 course meal. We got them back a second time at our own expense. The Villa is well appointed with an on-site caretaker. You must have a car if you stay here.see more

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