Apartments in Monteriggioni and Houses – Holiday Lettings - Holiday Rentals Monteriggioni

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5,818 Holiday homes

(3) Excellent 

    6

    Apartment rental in Monteriggioni

    Province of Siena / Monteriggioni

    3 4 1 night min

    • 3 bedrooms
    • sleeps 4
    • 1 night min

    from £100 / night

    £669 / week

    Book View

    from £100 / night

    (10) Excellent 

      41

      Holiday villa with shared pool in Monteriggioni

      Province of Siena / Monteriggioni

      6 18 min stay varies

      • 6 bedrooms
      • sleeps 18
      • min stay varies
      • Nearest beach 76 km
      • Swimming pool
      • Child friendly

      from £129 / night

      £902 / week

      Book View

      Responds fast!
      avg. 1 hour 47 minutes

      from £129 / night

        6

        Holiday home with swimming pool in Monteriggioni

        Province of Siena / Monteriggioni

        1 4 7 nights min

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

        from £248 / night

        £1,734 / week

        Book View

        Responds fast!
        avg. 27 minutes

        from £248 / night

          46

          Monteriggioni holiday apartment rental

          Province of Siena / Monteriggioni

          2 6 1 night min

          • 2 bedrooms
          • sleeps 6
          • 1 night min
          • Nearest beach 84 km
          • Swimming pool
          • Child friendly

          from £198 / night

          £1,387 / week

          Book View

          Responds fast!
          avg. 2 hours 29 minutes

          from £198 / night

          (9) Very Good 

            25

            Holiday apartment in Monteriggioni

            Province of Siena / Monteriggioni

            1 3 min stay varies

            • 1 bedroom
            • sleeps 3
            • min stay varies
            • Nearest beach 60 km
            • Child friendly
            • Pet friendly

            from £50 / night

            £347 / week

            Book View

            Responds fast!
            avg. 36 minutes

            from £50 / night

            (5) Excellent 

              34

              Holiday farmhouse with swimming pool in Monteriggioni

              Province of Siena / Monteriggioni

              1 2 2 nights min

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

              from £90 / night

              £624 / week

              Book View

              Responds fast!
              avg. 2 hours 42 minutes

              from £90 / night

              (2) Excellent 

                14

                Monteriggioni holiday b&b rental

                Province of Siena / Monteriggioni

                2 4 3 nights min

                • 2 bedrooms
                • sleeps 4
                • 3 nights min
                • Ask owner if suitable for children
                • Air conditioning
                • Pet friendly

                from £70 / night

                £446 - £931 / week

                Book View

                from £70 / night

                  20

                  Monteriggioni holiday apartment rental

                  Province of Siena / Monteriggioni

                  1 2 7 nights min

                  • 1 bedroom
                  • sleeps 2
                  • 7 nights min
                  • Air conditioning

                  from £43 / night

                  £298 / week

                  Book View

                  from £43 / night

                  (2) Very Good 

                    27

                    Holiday barn with swimming pool in Quercegrossa

                    Monteriggioni / Quercegrossa

                    1 3 min stay varies

                    • 1 bedroom
                    • sleeps 3
                    • min stay varies
                    • Nearest beach 80 km
                    • Swimming pool
                    • Child friendly

                    from £85 / night

                    £486 - £922 / week

                    Book View

                    from £85 / night

                      6

                      Holiday b&b in Monteriggioni

                      Province of Siena / Monteriggioni

                      3 6 1 night min

                      • 3 bedrooms
                      • sleeps 6
                      • 1 night min
                      • Child friendly
                      • Ask about pets

                      from £149 / night

                      £991 / week

                      Book View

                      from £149 / night

                      (1) Excellent 

                        19

                        Holiday apartment in Monteriggioni

                        Province of Siena / Monteriggioni

                        1 4 3 nights min

                        • 1 bedroom
                        • sleeps 4
                        • 3 nights min
                        • Nearest beach 100 km
                        • Child friendly
                        • Private garden

                        from £85 / night

                        £590 / week

                        Book View

                        from £85 / night

                        (1) Excellent 

                          43

                          Monteriggioni holiday apartment accommodation

                          Province of Siena / Monteriggioni

                          3 8 1 night min

                          • 3 bedrooms
                          • sleeps 8
                          • 1 night min
                          • Nearest beach 84 km
                          • Swimming pool
                          • Child friendly

                          from £199 / night

                          £1,387 / week

                          Book View

                          Responds fast!
                          avg. 2 hours 29 minutes

                          from £199 / night

                            34

                            Holiday villa in Monteriggioni

                            Province of Siena / Monteriggioni

                            3 5 7 nights min

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

                            from £112 / night

                            £783 - £1,110 / week

                            Book View

                            from £112 / night

                            (6) Excellent 

                              22

                              Apartment rental in Monteriggioni with swimming pool

                              Province of Siena / Monteriggioni

                              2 5 1 night min

                              • 2 bedrooms
                              • sleeps 5
                              • 1 night min
                              • Nearest beach 100 km
                              • Swimming pool
                              • Child friendly

                              from £70 / night

                              £446 - £550 / week

                              Book View

                              from £70 / night

                                24

                                Holiday farmhouse rental

                                Province of Siena / Monteriggioni

                                2 8 3 nights min

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

                                from £65 / night

                                £451 / week

                                Book View

                                from £65 / night

                                (4) Excellent 

                                  31

                                  Holiday farmhouse with swimming pool in Monteriggioni

                                  Province of Siena / Monteriggioni

                                  1 2 3 nights min

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

                                  from £90 / night

                                  £624 / week

                                  Book View

                                  Responds fast!
                                  avg. 2 hours 42 minutes

                                  from £90 / night

                                    23

                                    Holiday farmhouse with swimming pool in Monteriggioni

                                    Province of Siena / Monteriggioni

                                    1 24 2 nights min

                                    • 1 bedroom
                                    • sleeps 24
                                    • 2 nights min
                                    • Swimming pool
                                    • Child friendly
                                    • Air conditioning

                                    from £129 / night

                                    £902 / week

                                    Book View

                                    from £129 / night

                                    (7) Excellent 

                                      22

                                      Holiday home letting

                                      Province of Siena / Monteriggioni

                                      2 5 2 nights min

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

                                      from £90 / night

                                      £595 - £1,209 / week

                                      Book View

                                      Responds fast!
                                      avg. 1 hour 48 minutes

                                      from £90 / night

                                        17

                                        Holiday apartment in Monteriggioni

                                        Province of Siena / Monteriggioni

                                        2 4 1 night min

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

                                        from £45 / night

                                        £312 / week

                                        Book View

                                        from £45 / night

                                          25

                                          Holiday apartment with shared pool in Castellina Scalo

                                          Monteriggioni / Castellina Scalo

                                          2 4 min stay varies

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

                                          from £81 / night

                                          £564 - £1,194 / week

                                          Book View

                                          Responds fast!
                                          avg. 1 hour 30 minutes

                                          from £81 / night

                                            8

                                            Monteriggioni holiday home rental

                                            Province of Siena / Monteriggioni

                                            4 8 min stay varies

                                            • 4 bedrooms
                                            • sleeps 8
                                            • min stay varies
                                            • Nearest beach 100 km
                                            • Swimming pool
                                            • Suitable for children age 5+

                                            Pricing unknown

                                            Book View

                                            Pricing unknown

                                              19

                                              Holiday home rental

                                              Province of Siena / Monteriggioni

                                              15 30 min stay varies

                                              • 15 bedrooms
                                              • sleeps 30
                                              • min stay varies
                                              • Nearest beach 84 km
                                              • Swimming pool
                                              • Child friendly

                                              Pricing unknown

                                              Book View

                                              Responds fast!
                                              avg. 2 hours 29 minutes

                                              Pricing unknown

                                                18

                                                Apartment rental in Monteriggioni

                                                Province of Siena / Monteriggioni

                                                2 6 7 nights min

                                                • 2 bedrooms
                                                • sleeps 6
                                                • 7 nights min
                                                • Child friendly
                                                • Pet friendly

                                                from £77 / night

                                                £534 - £929 / week

                                                Book View

                                                Responds fast!
                                                avg. 2 hours 13 minutes

                                                from £77 / night

                                                  4

                                                  Holiday farmhouse with shared pool, golf nearby in Monteriggioni

                                                  Province of Siena / Monteriggioni

                                                  1 2 min stay varies

                                                  • 1 bedroom
                                                  • sleeps 2
                                                  • min stay varies
                                                  • Nearest beach 60 km
                                                  • Swimming pool
                                                  • Child friendly

                                                  Pricing unknown

                                                  Book View

                                                  Pricing unknown

                                                    20

                                                    Castellina Scalo holiday home rental

                                                    Monteriggioni / Castellina Scalo

                                                    2 4 min stay varies

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

                                                    from £79 / night

                                                    £550 - £1,194 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 2 hours 9 minutes

                                                    from £79 / night

                                                      15

                                                      Holiday villa rental

                                                      Monteriggioni / Quercegrossa

                                                      1 3 7 nights min

                                                      • 1 bedroom
                                                      • sleeps 3
                                                      • 7 nights min
                                                      • Swimming pool
                                                      • Child friendly
                                                      • Air conditioning

                                                      from £148 / night

                                                      £1,033 - £1,261 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 2 hours 13 minutes

                                                      from £148 / night

                                                      (2) Excellent 

                                                        12

                                                        Monteriggioni holiday hotel apartment rental

                                                        Province of Siena / Monteriggioni

                                                        10 20 min stay varies

                                                        • 10 bedrooms
                                                        • sleeps 20
                                                        • min stay varies
                                                        • Nearest beach 70 km
                                                        • Swimming pool
                                                        • Air conditioning

                                                        Pricing unknown

                                                        Book View

                                                        Pricing unknown

                                                          18

                                                          Home rental in Monteriggioni

                                                          Province of Siena / Monteriggioni

                                                          2 6 min stay varies

                                                          • 2 bedrooms
                                                          • sleeps 6
                                                          • min stay varies
                                                          • Child friendly
                                                          • Pet friendly

                                                          from £51 / night

                                                          £354 - £673 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 2 hours 22 minutes

                                                          from £51 / night

                                                            20

                                                            Castellina Scalo holiday home rental

                                                            Monteriggioni / Castellina Scalo

                                                            2 4 min stay varies

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

                                                            from £72 / night

                                                            £500 - £1,194 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 2 hours 22 minutes

                                                            from £72 / night

                                                              45

                                                              Monteriggioni holiday home rental

                                                              Province of Siena / Monteriggioni

                                                              6 14 7 nights min

                                                              • 6 bedrooms
                                                              • sleeps 14
                                                              • 7 nights min
                                                              • Swimming pool
                                                              • Child friendly

                                                              from £223 / night

                                                              £1,491 - £4,150 / week

                                                              Book View

                                                              from £223 / night

                                                              (5) Excellent 

                                                                53

                                                                Monteriggioni holiday villa rental

                                                                Province of Siena / Monteriggioni

                                                                2 6 7 nights min

                                                                • 2 bedrooms
                                                                • sleeps 6
                                                                • 7 nights min
                                                                • Nearest beach 80 km
                                                                • Swimming pool
                                                                • Child friendly

                                                                from £107 / night

                                                                £743 - £2,051 / week

                                                                Book View

                                                                from £107 / night

                                                                  19

                                                                  Holiday apartment in Quercegrossa

                                                                  Monteriggioni / Quercegrossa

                                                                  1 2 7 nights min

                                                                  • 1 bedroom
                                                                  • sleeps 2
                                                                  • 7 nights min
                                                                  • Child friendly
                                                                  • Air conditioning
                                                                  • Ask about pets

                                                                  from £99 / night

                                                                  £690 - £1,215 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 2 hours 13 minutes

                                                                  from £99 / night

                                                                    14

                                                                    Holiday home in Monteriggioni

                                                                    Province of Siena / Monteriggioni

                                                                    1 3 min stay varies

                                                                    • 1 bedroom
                                                                    • sleeps 3
                                                                    • min stay varies
                                                                    • Child friendly
                                                                    • Pet friendly

                                                                    from £38 / night

                                                                    £264 - £465 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 2 hours 9 minutes

                                                                    from £38 / night

                                                                      14

                                                                      Holiday apartment with shared pool in Monteriggioni

                                                                      Province of Siena / Monteriggioni

                                                                      2 5 7 nights min

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

                                                                      from £83 / night

                                                                      £575 - £1,061 / week

                                                                      Book View

                                                                      Responds fast!
                                                                      avg. 2 hours 13 minutes

                                                                      from £83 / night

                                                                        35

                                                                        Holiday home in Quercegrossa

                                                                        Monteriggioni / Quercegrossa

                                                                        5 10 min stay varies

                                                                        • 5 bedrooms
                                                                        • sleeps 10
                                                                        • min stay varies
                                                                        • Child friendly

                                                                        from £234 / night

                                                                        £1,637 - £3,599 / week

                                                                        Book View

                                                                        Responds fast!
                                                                        avg. 2 hours 22 minutes

                                                                        from £234 / night

                                                                        (1) Average 

                                                                          38

                                                                          Apartment rental in Monteriggioni with shared pool

                                                                          Province of Siena / Monteriggioni

                                                                          1 2 min stay varies

                                                                          • 1 bedroom
                                                                          • sleeps 2
                                                                          • min stay varies
                                                                          • Nearest beach 84 km
                                                                          • Swimming pool
                                                                          • Child friendly

                                                                          Pricing unknown

                                                                          Book View

                                                                          Responds fast!
                                                                          avg. 2 hours 29 minutes

                                                                          Pricing unknown

                                                                            36

                                                                            Holiday apartment in Monteriggioni

                                                                            Province of Siena / Monteriggioni

                                                                            1 4 min stay varies

                                                                            • 1 bedroom
                                                                            • sleeps 4
                                                                            • min stay varies
                                                                            • Nearest beach 84 km
                                                                            • Swimming pool
                                                                            • Child friendly

                                                                            Pricing unknown

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 2 hours 29 minutes

                                                                            Pricing unknown

                                                                            (1) Excellent 

                                                                              13

                                                                              Monteriggioni holiday villa rental

                                                                              Province of Siena / Monteriggioni

                                                                              3 6 min stay varies

                                                                              • 3 bedrooms
                                                                              • sleeps 6
                                                                              • min stay varies
                                                                              • Nearest beach 100 km
                                                                              • Swimming pool
                                                                              • Private garden

                                                                              Pricing unknown

                                                                              Book View

                                                                              Pricing unknown

                                                                                20

                                                                                Holiday apartment with shared pool in Quercegrossa

                                                                                Monteriggioni / Quercegrossa

                                                                                2 4 7 nights min

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

                                                                                from £136 / night

                                                                                £947 - £1,722 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 2 hours 13 minutes

                                                                                from £136 / night

                                                                                  25

                                                                                  Holiday apartment with shared pool in Castellina Scalo

                                                                                  Monteriggioni / Castellina Scalo

                                                                                  2 4 7 nights min

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

                                                                                  from £108 / night

                                                                                  £750 - £1,345 / week

                                                                                  Book View

                                                                                  Responds fast!
                                                                                  avg. 2 hours 13 minutes

                                                                                  from £108 / night

                                                                                  Top Destination reviews

                                                                                  Farmhouse in old mill in the Chianti hills
                                                                                  A fantastic Tuscany retreat

                                                                                  We spent 2 weeks in the guest residence and found the location ideal to visit all of the wonders Tuscany has to offer with even a train station that will take you to Siena in 15 minutes within walking distance if you prefer not to drive. Monteriggioni is a short walk away along footpaths and the whole area is beautiful. The property had everything we as a family of 4 needed plus the added Tuscany charm of a traditional building. My children used the pool every day we were there and we couldn't fault the pool area and gardens for appearance and facilities. The owners are very friendly, available when you need them and can offer a lot of help with deciding where to go or on practical matters such as which supermarket to go to. We were also helped out by the owners with a wine tour booking while we were there which we enjoyed thoroughly. We left with a lot of fond memories of our stay and a camera full of beautiful photographs.see more
                                                                                  Agriturismo Sammonti
                                                                                  Beautiful apartment in glorious country setting in easy reach of Florence, Sienna and other picturesque Tuscan towns

                                                                                  Our host, Grazia, was spot on, really lovely. We were able to communicate in a hilarious mixture of English and Italian. She was friendly, enthusiastic about the region giving lots of top tips and local knowledge about places to visit, bus routes, best places to park etc. Grazia provided a good selection of useful English brochures for the surrounding area and some town/city maps. She was very welcoming but left us to it otherwise and didn't interfere. The apartment felt very private. The apartment was spacious and cool with everything you could possibly need. If it was, by a miracle, missing something rest assured that Grazia could find it! It was supplied with basic condiments, homemade olive oil and fresh fruit from the garden. Every so often other fresh treats appeared on the terrace (grapes, honey etc). The wifi was strongest in the lounge and on the terrace, a little weak in the bedroom. The view from the terrace was breathtaking with a great panorama of Tuscan countryside, including the towers of San Gimignano. The pool was lovely and clean and a great afternoon sun trap. Watch out for mosquitoes at dusk. Fruit trees surround the pool (pomegranates, figs, olive trees) and make it quite special. The car was essential here to enable trips to the local town (Colle di Val d'Elsa) for supplies and for days out (Volterra, San Gimignano etc). It's also possible to drive and park in Sienna in about 40 minutes. On Grazia's recommendation we took the bus to Florence. It was cheap and easy. On our last night we ate at Antico Borgo Poggiarello (which is basically the end of Grazia's road). The food was a set menu of 4 courses and was amazing. Walkable in 15 mins or 5 mins in a car. We loved our stay and would definitely recommend to others. It's a great apartment to relax in or to use as a base for exploring.see more
                                                                                  Beatifull villa with private pool
                                                                                  Peaceful oasis

                                                                                  A beautiful villa situated in a well designed and cared for large lush garden. We loved the sprinklers that automatically came on at about 6.30am each morning! The house is perfectly formed. The large veranda perfect for taking shade. The swimming pool is deep enough to play lots of diving games as well as cool down. Spectacular views in all directions. We all returned feeling relaxed and rested. Carlo is a fabulous host with great restaurant recommendations!see more
                                                                                  Agriturismo Sammonti
                                                                                  Perfect week in Tuscany

                                                                                  All previous positive reviews reflect our experience. Beautiful, quiet location. Lovely hosts. The house was cosy and a great place to come home to after sightseeing. It was also very easy to spend a whole day in the local area or enjoying the pool and garden. Thank you to Grazia and her husband for the great care and attention they have put into the apartment and the kindness they showed our daughter.see more

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