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

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4,110 Holiday homes

(16) Excellent 

    17

    Siena holiday home rental

    Province of Siena / Siena

    2 3 3 nights min

    • 2 bedrooms
    • sleeps 3
    • 3 nights min
    • Nearest beach 95 km
    • Child friendly
    • Pet friendly

    from £86 / night

    £600 / week

    Book View

    from £86 / night

    (18) Very Good 

    Certificate of Excellence

      18

      Apartment rental in Siena

      Province of Siena / Siena

      1 4 min stay varies

      • 1 bedroom
      • sleeps 4
      • min stay varies
      • Nearest beach 105 km
      • Swimming pool
      • Car not necessary

      Certificate of Excellence

      from £101 / night

      £1,128 / week

      Book View

      from £101 / night

      (2) Excellent 

        22

        Caprera holiday apartment rental

        Siena / Caprera

        1 2 5 nights min

        • 1 bedroom
        • sleeps 2
        • 5 nights min
        • Nearest beach 100 km
        • Child friendly
        • Air conditioning

        from £81 / night

        £504 / week

        Book View

        from £81 / night

          17

          Holiday apartment in Siena

          Province of Siena / Siena

          2 4 2 nights min

          • 2 bedrooms
          • sleeps 4
          • 2 nights min
          • Child friendly
          • Ask about pets

          from £96 / night

          £595 / week

          Book View

          Responds fast!
          avg. 3 hours 22 minutes

          from £96 / night

          (1) Excellent 

            6

            Apartment rental in Siena

            Province of Siena / Siena

            2 4 1 night min

            • 2 bedrooms
            • sleeps 4
            • 1 night min
            • Child friendly
            • Air conditioning
            • Pet friendly

            from £66 / night

            £303 / week

            Book View

            Responds fast!
            avg. 8 minutes

            from £66 / night

            (9) Excellent 

              31

              Holiday villa in Costalpino

              Siena / Costalpino

              3 8 min stay varies

              • 3 bedrooms
              • sleeps 8
              • min stay varies
              • Child friendly
              • Private garden

              from £227 / night

              £1,612 - £1,964 / week

              Book View

              from £227 / night

                30

                Holiday apartment in Siena

                Province of Siena / Siena

                1 5 min stay varies

                • 1 bedroom
                • sleeps 5
                • min stay varies
                • Child friendly
                • Air conditioning
                • Pet friendly

                from £65 / night

                £452 / week

                Book View

                from £65 / night

                  4

                  Holiday b&b in Siena

                  Province of Siena / Siena

                  2 4 1 night min

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

                  from £76 / night

                  £529 / week

                  Book View

                  from £76 / night

                    15

                    Siena holiday b&b rental

                    Province of Siena / Siena

                    1 2 3 nights min

                    • 1 bedroom
                    • sleeps 2
                    • 3 nights min
                    • Nearest beach 80 km
                    • Child friendly
                    • Air conditioning

                    from £99 / night

                    £529 / week

                    Book View

                    from £99 / night

                      19

                      Holiday farmhouse in Costalpino

                      Siena / Costalpino

                      2 4 min stay varies

                      • 2 bedrooms
                      • sleeps 4
                      • min stay varies
                      • Child friendly

                      from £70 / night

                      £487 / week

                      Book View

                      Responds fast!
                      avg. 3 hours 22 minutes

                      from £70 / night

                      (9) Excellent 

                      Certificate of Excellence

                        16

                        Holiday apartment with swimming pool in Siena

                        Province of Siena / Siena

                        1 4 min stay varies

                        • 1 bedroom
                        • sleeps 4
                        • min stay varies
                        • Nearest beach 83 km
                        • Swimming pool
                        • Child friendly

                        Certificate of Excellence

                        from £121 / night

                        £685 - £1,289 / week

                        Book View

                        Responds fast!
                        avg. 2 hours 20 minutes

                        from £121 / night

                        (4) Excellent 

                          40

                          Holiday villa with swimming pool in Siena

                          Province of Siena / Siena

                          3 7 7 nights min

                          • 3 bedrooms
                          • sleeps 7
                          • 7 nights min
                          • Nearest beach 100 km
                          • Swimming pool
                          • Child friendly

                          from £128 / night

                          £897 - £2,054 / week

                          Book View

                          from £128 / night

                          (9) Excellent 

                            17

                            Holiday home in Siena

                            Province of Siena / Siena

                            1 4 min stay varies

                            • 1 bedroom
                            • sleeps 4
                            • min stay varies
                            • Nearest beach 70 km
                            • Child friendly
                            • Ask about pets

                            from £96 / night

                            £655 / week

                            Book View

                            Responds fast!
                            avg. 3 hours 9 minutes

                            from £96 / night

                              21

                              Isola d'Arbia holiday farmhouse rental

                              Siena / Isola d'Arbia

                              1 4 7 nights min

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

                              from £202 / night

                              £1,410 / week

                              Book View

                              Responds fast!
                              avg. 3 hours 34 minutes

                              from £202 / night

                              (1) Excellent 

                                42

                                Holiday villa with shared pool in Siena

                                Province of Siena / Siena

                                4 4 7 nights min

                                • 4 bedrooms
                                • sleeps 4
                                • 7 nights min
                                • Nearest beach 110 km
                                • Swimming pool
                                • Child friendly

                                from £143 / night

                                £1,001 - £1,763 / week

                                Book View

                                Responds fast!
                                avg. 2 hours 24 minutes

                                from £143 / night

                                  29

                                  Apartment letting in Siena

                                  Province of Siena / Siena

                                  1 2 3 nights min

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

                                  from £106 / night

                                  £529 / week

                                  Book View

                                  from £106 / night

                                  (11) Very Good 

                                    18

                                    Condo rental in Siena

                                    Province of Siena / Siena

                                    1 4 min stay varies

                                    • 1 bedroom
                                    • sleeps 4
                                    • min stay varies
                                    • Nearest beach 95 km
                                    • Child friendly
                                    • Car not necessary

                                    from £76 / night

                                    £605 - £887 / week

                                    Book View

                                    from £76 / night

                                    (1) Very Good 

                                      24

                                      Monastero holiday farmhouse let

                                      Siena / Monastero

                                      1 4 5 nights min

                                      • 1 bedroom
                                      • sleeps 4
                                      • 5 nights min
                                      • Nearest beach 100 km
                                      • Child friendly
                                      • Air conditioning

                                      from £106 / night

                                      £666 - £856 / week

                                      Book View

                                      from £106 / night

                                      (2) Excellent 

                                        19

                                        Holiday apartment rental

                                        Province of Siena / Siena

                                        2 4 min stay varies

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

                                        from £121 / night

                                        £846 / week

                                        Book View

                                        Responds fast!
                                        avg. 1 hour 28 minutes

                                        from £121 / night

                                        (8) Excellent 

                                          24

                                          Farmhouse rental in Caprera

                                          Siena / Caprera

                                          3 6 5 nights min

                                          • 3 bedrooms
                                          • sleeps 6
                                          • 5 nights min
                                          • Nearest beach 100 km
                                          • Child friendly
                                          • Air conditioning

                                          from £187 / night

                                          £1,174 - £1,587 / week

                                          Book View

                                          from £187 / night

                                          (2) Excellent 

                                            22

                                            Holiday apartment in Val di Merse

                                            Siena / Val di Merse

                                            1 2 min stay varies

                                            • 1 bedroom
                                            • sleeps 2
                                            • min stay varies
                                            • Beach / lakeside relaxation
                                            • Nearest beach 70 km
                                            • Child friendly

                                            from £71 / night

                                            £454 / week

                                            Book View

                                            Responds fast!
                                            avg. 1 hour 29 minutes

                                            from £71 / night

                                              11

                                              Holiday apartment in Siena

                                              Province of Siena / Siena

                                              1 4 1 night min

                                              • 1 bedroom
                                              • sleeps 4
                                              • 1 night min
                                              • Nearest beach 81 km
                                              • Swimming pool
                                              • Private garden

                                              from £96 / night

                                              £670 / week

                                              Book View

                                              from £96 / night

                                              (6) Very Good 

                                                24

                                                Holiday apartment rental

                                                Siena / Val di Merse

                                                3 7 min stay varies

                                                • 3 bedrooms
                                                • sleeps 7
                                                • min stay varies
                                                • Beach / lakeside relaxation
                                                • Nearest beach 70 km
                                                • Child friendly

                                                from £202 / night

                                                £1,108 - £1,410 / week

                                                Book View

                                                Responds fast!
                                                avg. 1 hour 29 minutes

                                                from £202 / night

                                                (8) Excellent 

                                                  18

                                                  Apartment rental in Siena with shared pool

                                                  Province of Siena / Siena

                                                  2 4 min stay varies

                                                  • 2 bedrooms
                                                  • sleeps 4
                                                  • min stay varies
                                                  • Nearest beach 95 km
                                                  • Swimming pool
                                                  • Child friendly

                                                  from £101 / night

                                                  £655 - £1,209 / week

                                                  Book View

                                                  from £101 / night

                                                  (1) Excellent 

                                                    19

                                                    Siena holiday apartment rental

                                                    Province of Siena / Siena

                                                    4 8 min stay varies

                                                    • 4 bedrooms
                                                    • sleeps 8
                                                    • min stay varies
                                                    • Nearest beach 95 km
                                                    • Swimming pool
                                                    • Child friendly

                                                    from £202 / night

                                                    £1,159 - £2,115 / week

                                                    Book View

                                                    from £202 / night

                                                      15

                                                      Siena holiday farmhouse rental

                                                      Province of Siena / Siena

                                                      2 4 min stay varies

                                                      • 2 bedrooms
                                                      • sleeps 4
                                                      • min stay varies
                                                      • Nearest beach 83 km
                                                      • Swimming pool
                                                      • Child friendly

                                                      from £121 / night

                                                      £685 - £1,289 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 2 hours 20 minutes

                                                      from £121 / night

                                                      (23) Very Good 

                                                      Certificate of Excellence

                                                        51

                                                        Holiday cottage in Siena

                                                        Province of Siena / Siena

                                                        1 2 min stay varies

                                                        • 1 bedroom
                                                        • sleeps 2
                                                        • min stay varies
                                                        • Beach / lakeside relaxation
                                                        • Nearest beach 65 km
                                                        • Air conditioning

                                                        Certificate of Excellence

                                                        from £99 / night

                                                        £691 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 3 hours 24 minutes

                                                        from £99 / night

                                                        (4) Very Good 

                                                          21

                                                          Apartment rental in Siena

                                                          Province of Siena / Siena

                                                          1 5 min stay varies

                                                          • 1 bedroom
                                                          • sleeps 5
                                                          • min stay varies
                                                          • Child friendly
                                                          • Car not necessary
                                                          • Air conditioning

                                                          from £68 / night

                                                          £473 / week

                                                          Book View

                                                          from £68 / night

                                                          (1) Very Good 

                                                            20

                                                            Siena holiday apartment rental

                                                            Province of Siena / Siena

                                                            2 4 1 night min

                                                            • 2 bedrooms
                                                            • sleeps 4
                                                            • 1 night min
                                                            • Child friendly
                                                            • Car not necessary
                                                            • Pet friendly

                                                            from £80 / night

                                                            £503 - £785 / week

                                                            Book View

                                                            from £80 / night

                                                              48

                                                              Holiday villa with swimming pool in Siena

                                                              Province of Siena / Siena

                                                              2 5 min stay varies

                                                              • 2 bedrooms
                                                              • sleeps 5
                                                              • min stay varies
                                                              • Nearest beach 95 km
                                                              • Swimming pool
                                                              • Child friendly

                                                              from £197 / night

                                                              £978 - £2,437 / week

                                                              Enquire View

                                                              from £197 / night

                                                              (1) Excellent 

                                                                24

                                                                Holiday apartment in Val di Merse

                                                                Siena / Val di Merse

                                                                6 14 min stay varies

                                                                • 6 bedrooms
                                                                • sleeps 14
                                                                • min stay varies
                                                                • Beach / lakeside relaxation
                                                                • Nearest beach 70 km
                                                                • Child friendly

                                                                from £303 / night

                                                                £2,015 - £2,417 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 1 hour 29 minutes

                                                                from £303 / night

                                                                (8) Very Good 

                                                                  30

                                                                  Siena holiday apartment rental

                                                                  Province of Siena / Siena

                                                                  2 4 3 nights min

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

                                                                  from £151 / night

                                                                  £907 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 3 hours 59 minutes

                                                                  from £151 / night

                                                                  (6) Excellent 

                                                                    19

                                                                    Siena holiday apartment rental

                                                                    Province of Siena / Siena

                                                                    2 4 1 night min

                                                                    • 2 bedrooms
                                                                    • sleeps 4
                                                                    • 1 night min
                                                                    • Child friendly
                                                                    • Car not necessary
                                                                    • Air conditioning

                                                                    from £81 / night

                                                                    £504 - £786 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 1 hour 51 minutes

                                                                    from £81 / night

                                                                    (2) Excellent 

                                                                      19

                                                                      Holiday apartment in Siena

                                                                      Province of Siena / Siena

                                                                      2 4 2 nights min

                                                                      • 2 bedrooms
                                                                      • sleeps 4
                                                                      • 2 nights min
                                                                      • Nearest beach 95 km
                                                                      • Child friendly
                                                                      • Air conditioning

                                                                      from £373 / night

                                                                      £2,417 / week

                                                                      Book View

                                                                      from £373 / night

                                                                      (2) Excellent 

                                                                        45

                                                                        Siena holiday apartment rental

                                                                        Province of Siena / Siena

                                                                        1 3 min stay varies

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

                                                                        from £55 / night

                                                                        £381 / week

                                                                        Book View

                                                                        from £55 / night

                                                                        (4) Excellent 

                                                                          27

                                                                          Holiday apartment rental

                                                                          Province of Siena / Siena

                                                                          1 4 7 nights min

                                                                          • 1 bedroom
                                                                          • sleeps 4
                                                                          • 7 nights min
                                                                          • Nearest beach 80 km
                                                                          • Swimming pool
                                                                          • Child friendly

                                                                          from £71 / night

                                                                          £494 - £1,007 / week

                                                                          Book View

                                                                          from £71 / night

                                                                          (2) Excellent 

                                                                            18

                                                                            Holiday apartment in Siena

                                                                            Province of Siena / Siena

                                                                            1 3 2 nights min

                                                                            • 1 bedroom
                                                                            • sleeps 3
                                                                            • 2 nights min
                                                                            • Child friendly
                                                                            • Air conditioning

                                                                            from £76 / night

                                                                            £454 - £766 / week

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 3 hours 10 minutes

                                                                            from £76 / night

                                                                              40

                                                                              Holiday apartment in Siena

                                                                              Province of Siena / Siena

                                                                              3 9 2 nights min

                                                                              • 3 bedrooms
                                                                              • sleeps 9
                                                                              • 2 nights min
                                                                              • Child friendly

                                                                              from £202 / night

                                                                              £1,410 / week

                                                                              Book View

                                                                              from £202 / night

                                                                              (4) Excellent 

                                                                                26

                                                                                Villa rental in Siena with swimming pool

                                                                                Province of Siena / Siena

                                                                                9 18 min stay varies

                                                                                • 9 bedrooms
                                                                                • sleeps 18
                                                                                • min stay varies
                                                                                • Nearest beach 95 km
                                                                                • Swimming pool
                                                                                • Child friendly

                                                                                from £454 / night

                                                                                £2,518 - £4,432 / week

                                                                                Book View

                                                                                from £454 / night

                                                                                  40

                                                                                  Holiday apartment with shared pool in Siena

                                                                                  Province of Siena / Siena

                                                                                  3 7 min stay varies

                                                                                  • 3 bedrooms
                                                                                  • sleeps 7
                                                                                  • min stay varies
                                                                                  • Swimming pool
                                                                                  • Suitable for children age 5+
                                                                                  • Ask about pets

                                                                                  from £645 / night

                                                                                  £4,331 - £4,583 / week

                                                                                  Book View

                                                                                  from £645 / night

                                                                                  Top Destination reviews

                                                                                  Luxury apartment in Siena, Tuscany
                                                                                  New architectural marvel in medieval building

                                                                                  A beautiful, spacious flat to explore Siena from. We had huge amounts of fun finding the flying bathroom, false ceiling and how the flat fitted around the other apartments in the building. The roof terrace was great and got sun from around 9:30 in the morning. … see more
                                                                                  Apartment Camilla, countryside, not far from Siena
                                                                                  Heaven on Earth

                                                                                  This Villa Apartment was absolutely awesome! The own was the most kind and gentle man you could ever meet! The apartment was huge and way more than we expected. The furnishings were beautiful and all the rooms were very large. Absolutely loved the showers and Jacuzzi. We were greeted with Tuscan pastries, a bottle of red wine and a bottle of Prosecco, a bottle of Coke and a large bottle of water. The owner gave us a tour of the entire group of apartments and what a surprise to find out that he had a small venue for intimate weddings or private catered parties! The grounds are gorgeous complete with swimming pool and if you can believe this they even have a dance studio with tango lessons offered!! This is a restored 1850 Villa that absolutely ranks in the top 10 and I will stay here again in a heart beat! For all those looking for a intimate wedding setting! This Villa has it all and lodging for 22 people! Perfect for a destination wedding! There are also two small towns near by they have great restaurants with excellent food and ridiculously low prices. The food is all home made from scratch in both places including the pastas. I feel I must include thee names: La Compania in Sovicille and la Logge in Rossia!! You will not be disappointed. Ciao and bouna vacanza!!see more
                                                                                  A Jewel in Siena
                                                                                  A very good apartment

                                                                                  A very good and big apartment in a quiet area - close to the historical towncenter. Shops and restaurants in the neighbourhood. Comfortable rooms, big kitchen/diningroom, beautiful outdoor areal, a fine familyhome - and a kind hostess. … see more
                                                                                  Elegant 2 bedroom apt. in historic Siena residence
                                                                                  This is an excellent apartment in the centre of Sienna.

                                                                                  This is a great apartment as is shown by the photos. It is a little difficult to find the first time but once located the task was simple. We found overnight car parking 10 minutes away for a cost of about 15 euro a night. Great apartment and an excellent host. … see more
                                                                                  Sienahomeandsailing-Red apartment
                                                                                  nice stay, central, clean

                                                                                  property was as advertised, very clean, easy access, central and very near to the central bus stop, owner came to pick us up at the bus station, we were very happy with our choice … see more
                                                                                  Stunning Tuscan views from traditional farmhouse 10mins to downtown Siena
                                                                                  Belvedere e stupendo

                                                                                  After a beautifully green, bus ride from Rome, I arrived at my designated stop a few kilometer’s before Siena and waited for my transfer to Belvedere, a magical home at the end of a beautiful long winding driveway where views of ‘Siena’s Il Duomo and the vineyards stretch as far as the eye can see. Belvedere has it all, the entertainment area with a barbeque area perfect for entertaining, an outside pizza oven, for easy suppers, and a beautiful antique dinner table for 10, beside a great fire place in case a dinner party in the middle of Tuscany takes your fancy. My personal favourite corner was the kitchen, with its cozy booth seat, where we all congregated each morning. The kitchen is so well equipped with all the conveniences you could wish for if cooking in numbers. There are three guest bedrooms, with lovely furnishing each with private en-suite which was a surprise and not a common finish in most guest houses. My second favourite spot was quite literally ‘Under the Tuscan Sun’ stretched on the sun chairs, with nothing more than the sound of a few bees. The guest handbook is impressive, with wonderful insight on the destination, and how to feel right at home. The owners have even taken the time to detail the best ways to conserve energy – Kudos You can also purchase wine and curio from the owners estate. I don’t think I could have asked for a better introduction to Tuscany, its’ beauty surpassed all expectation, and the comfort of feeling right at home will not be forgotten. I can definitely recommend Belvedere, as the perfect getaway for a couple or a few couples / friends and hope someday I will return. Bellisimo!see more
                                                                                  SORTOIANO apartaments in historic Tuscan property
                                                                                  What you imagine when you think "Tuscany"!

                                                                                  We stayed in La Verbena, and it was amazing. Podere Sortoiano is about 15 minutes out of Siena, but it is so worth it to stay out of the city! It's incredibly quiet and relaxing, and the stars are unlike anything you've ever seen. Our villa was extremely clean and had everything we needed to feel at home. Francesca was awesome and was extremely helpful, giving us great tips of towns to explore. We will definitely be back!see more
                                                                                  Anne
                                                                                  Very nice

                                                                                  Very nice flat in the city center. Welcoming perfect, and there Wonderful hosts and a fantastic spot for getting away from it allis a free parking 100 meters far. … see more
                                                                                  The Senesina
                                                                                  Truly a home away from home

                                                                                  The apartment is just as beautiful as the photos. It is 10km out of sienna but there are supermarkets, cafes etc within 3km. Andrea was the perfect host answering any questions promptly when we emailed him. The apartment was stocked with breakfast products for our first few days like jam, toast, croissants, coffee, tea, sugar and oils which was much appreciated. Beautiful surroundings and very comfortable property. Could not find fault with anything. Thank you Andrea.see more
                                                                                  La Stalla di San Lazzero, adorable house in Siena
                                                                                  What a wonderful stay! We highly recommend this house!

                                                                                  We instinctively felt in love with Leonardo's house the moment we arrived! The description we received from Leonardo how to get to the house was perfect and we immediately found the correct way (thank you!). Leonardo greeted us warmly and showed us around the house. The reality is even better than the beautiful pictures here on TripAdvisor. Everything was so clean and very tastefully furnished. We loved the new kitchen with the big fridge and gas stove, the red sofa, the outside sitting area and this view! It really became our little home away from home! Leonardo is a really nice, funny and helpful person, he was always available when we had questions and he helped us with his insider tips. :) And last but not least: Thank you for the flowers waiting for us on our arrival day! :)see more
                                                                                  Private, elegant zen cottage, 10 min. from Siena
                                                                                  Peaceful cottage in isolated location

                                                                                  Property although in an isolated location was fairly central for accessing all of the Tuscany region. All points requiring access were never any more than 1 hours drive away. Great base for touring. Property has no air conditioning therefore reliant on 2 x fan coolers. Bedroom is on a galley level which has no toilet facility making night time visits a bit of a pain as you have to go downstairs. Ample space outside cottage. Were a pool in situ, this would be almost perfect.see more
                                                                                  Bright, spacious villa with pool near Siena
                                                                                  A charming Tuscan farmhouse villa

                                                                                  We stayed here for a most enjoyable week in September 2016. It is all that the owner Giada describes and she is a charming and helpful host. The villa, a converted stone farmhouse, is located on the outskirts of Siena, close to Quercegrossa. It is set in farmland and boasts an olive grove and a great swimming pool. There is ample car parking and immediate access to the Chianti wine region and the charming heritage sites of Tuscany.see more

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