Vacation Rentals & Villas in Montepulciano

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4,189 Houses

(28) Excellent 

    34

    Villa Nobile, Luxury Tuscan Home, Walk to Town

    Province of Siena / Montepulciano

    Montepulciano villa

    5 18 min stay varies

    • 5 bedrooms
    • sleeps 18
    • min stay varies
    • Nearest beach 152 mi
    • Swimming pool
    • Child Friendly

    Price per night from

    $859

    Responds fast!
    avg. 2 hours 32 minutes

    Price per night from

    $859

    (2) Excellent 

      17

      Very nice home in the historical center

      Montepulciano / Valiano

      Valiano apartment

      3 6 3 nights min

      • 3 bedrooms
      • sleeps 6
      • 3 nights min
      • Child Friendly
      • Pet Friendly

      Price per night from

      $94

      Price per night from

      $94

      (9) Excellent 

        36

        Charming Apartment in Historic Center of Montepulciano, Tuscany

        Province of Siena / Montepulciano

        Montepulciano apartment

        2 6 min stay varies

        • 2 bedrooms
        • sleeps 6
        • min stay varies
        • Child Friendly
        • Car not necessary
        • Air conditioning

        Price per night from

        $91

        Responds fast!
        avg. 2 hours 24 minutes

        Price per night from

        $91

        (1) Very Good 

          32

          Maramai

          Montepulciano / Abbadia di Montepulciano

          Abbadia di Montepulciano villa

          5 10 7 nights min

          • 5 bedrooms
          • sleeps 10
          • 7 nights min
          • Ask about children
          • Ask about pets

          Price per night from

          $482

          Responds fast!
          avg. 1 hour 5 minutes

          Price per night from

          $482

          (17) Excellent 

            38

            Tigli #1, two bedrooms apartment close to Montepulciano with Wi-Fi and pool

            Province of Siena / Montepulciano

            Montepulciano apartment

            2 6 min stay varies

            • 2 bedrooms
            • sleeps 6
            • min stay varies
            • Nearest beach 185 mi
            • Swimming pool
            • Child Friendly
            “Outstanding accommodations!” Tucked away and hard to find. There was a small wooden sign which we missed, but well worth the extra miles we had to drive. The property is well kept and can't beat the views. The apartment we had was a 2br and 2bath and
            …see more

            Price per night from

            $133

            Price per night from

            $133

            (2) Very Good 

              39

              Tigli #6, ground floor flat with one bedroom in Montepulciano area. Wi-Fi & pool

              Province of Siena / Montepulciano

              Montepulciano apartment

              1 2 min stay varies

              • 1 bedroom
              • sleeps 2
              • min stay varies
              • Nearest beach 185 mi
              • Swimming pool
              • Child Friendly
              “Wow! A relaxing well appointed holiday home” This is central rural position 6ks from Torrita di Siena makes it easy to enjoy beautiful Tuscany. With easy day trips with a car to Seina, Arezzo, Cortona, Castiglione del Lago or Firenze to name a few.Qu
              …see more

              Price per night from

              $94

              Price per night from

              $94

              (1) Excellent 

                29

                Colombi Palace Montepulciano

                Province of Siena / Montepulciano

                Montepulciano apartment

                2 4 2 nights min

                • 2 bedrooms
                • sleeps 4
                • 2 nights min
                • Beach / lakeside relaxation
                • Child Friendly
                • Air conditioning

                Price per night from

                $189

                Price per night from

                $189

                (1) Excellent 

                  39

                  Apartment "The Hague" at The House of the Oaks - Montepulciano

                  Montepulciano / Acquaviva di Montepulciano

                  Acquaviva di Montepulciano apartment

                  2 5 min stay varies

                  • 2 bedrooms
                  • sleeps 5
                  • min stay varies
                  • Nearest beach 120 mi
                  • Swimming pool
                  • Child Friendly

                  Price per night from

                  $143

                  Responds fast!
                  avg. 1 hour 58 minutes

                  Price per night from

                  $143

                    24

                    Villa Abbadia

                    Montepulciano / Abbadia di Montepulciano

                    Abbadia di Montepulciano villa

                    4 10 7 nights min

                    • 4 bedrooms
                    • sleeps 10
                    • 7 nights min
                    • Nearest beach 201 mi
                    • Swimming pool
                    • Child Friendly

                    Price per night from

                    $317

                    Price per night from

                    $317

                    (37) Excellent 

                      99

                      LA VALIANA Luxury Villa Rental (Montepulciano) - HEATED POOL Incl./ FREE WI-FI

                      Province of Siena / Montepulciano

                      Montepulciano villa

                      4 8 min stay varies

                      • 4 bedrooms
                      • sleeps 8
                      • min stay varies
                      • Beach / lakeside relaxation
                      • Nearest beach 15 mi
                      • Swimming pool
                      “Paradise in Tuscany!” This lovely villa has it all and is the kind of place that makes you want to stay and 'while away' the afternoon among its many outdoor spaces: whether it's dining in the gazebo overlooking the vineyard, watching as the evening
                      …see more

                      Price per night from

                      $651

                      Price per night from

                      $651

                        32

                        Maramai

                        Province of Siena / Montepulciano

                        Montepulciano villa

                        4 7 7 nights min

                        • 4 bedrooms
                        • sleeps 7
                        • 7 nights min
                        • Ask about children
                        • Ask about pets

                        Price per night from

                        $406

                        Responds fast!
                        avg. 1 hour 5 minutes

                        Price per night from

                        $406

                        (11) Excellent 

                          33

                          Tigli #5, flat near Montepulciano with 2 bedrooms. A/C, Wi-Fi and swimming pool

                          Province of Siena / Montepulciano

                          Montepulciano apartment

                          2 5 min stay varies

                          • 2 bedrooms
                          • sleeps 5
                          • min stay varies
                          • Nearest beach 185 mi
                          • Swimming pool
                          • Child Friendly
                          “Stunning estate and perfect location” I went with by partner in June for a 5 night stay after a couple nights in Florence. It was the perfect holiday and this appartment was exactly what we wanted - somewhere quiet, with a pool and close to Tuscan vi
                          …see more

                          Price per night from

                          $117

                          Price per night from

                          $117

                          (9) Very Good 

                            34

                            Tigli #2, apt Montepulciano area for 5 persons with A/C, Wi-Fi and swimming pool

                            Province of Siena / Montepulciano

                            Montepulciano apartment

                            3 6 min stay varies

                            • 3 bedrooms
                            • sleeps 6
                            • min stay varies
                            • Nearest beach 185 mi
                            • Swimming pool
                            • Child Friendly
                            “Stunning setting” The apartment complex ( once we found it with a little help!) was stunning and beautifully kept. Unfortunately we had an unseasonably cold week so couldn't make use of the pool and much of the outdoor areas although as our large balc
                            …see more

                            Price per night from

                            $133

                            Price per night from

                            $133

                            (2) Very Good 

                              10

                              Villa Iris - Perfect for families or group of friends

                              Province of Siena / Montepulciano

                              Montepulciano apartment

                              3 5 3 nights min

                              • 3 bedrooms
                              • sleeps 5
                              • 3 nights min
                              • Swimming pool
                              • Child Friendly
                              • Air conditioning

                              Price per night from

                              $224

                              Price per night from

                              $224

                                8

                                villa in South Toscany

                                Province of Siena / Montepulciano

                                Montepulciano villa

                                3 8 14 nights min

                                • 3 bedrooms
                                • sleeps 8
                                • 14 nights min
                                • Swimming pool
                                • Ask about children
                                • Air conditioning

                                Price per night from

                                $586

                                Responds fast!
                                avg. 29 minutes

                                Price per night from

                                $586

                                  37

                                  6 bedroom Villa in Castelluccio, Tuscany, Italy - 5395009

                                  Montepulciano / Bivio di San Biagio

                                  Bivio di San Biagio villa

                                  6 12 7 nights min

                                  • 6 bedrooms
                                  • sleeps 12
                                  • 7 nights min
                                  • Swimming pool
                                  • Child Friendly
                                  • Air conditioning

                                  Price per night from

                                  $919

                                  Price per night from

                                  $919

                                  (5) Excellent 

                                    36

                                    CasaMontepulciano Into the sunset

                                    Province of Siena / Montepulciano

                                    Montepulciano apartment

                                    2 4 2 nights min

                                    • 2 bedrooms
                                    • sleeps 4
                                    • 2 nights min
                                    • Child Friendly
                                    • Car not necessary
                                    • Ask about pets

                                    Price per night from

                                    $175

                                    Responds fast!
                                    avg. 1 hour 11 minutes

                                    Price per night from

                                    $175

                                      28

                                      Villa Croce

                                      Montepulciano / Sant'Albino

                                      Sant'Albino villa

                                      5 11 7 nights min

                                      • 5 bedrooms
                                      • sleeps 11
                                      • 7 nights min
                                      • Swimming pool
                                      • Child Friendly
                                      • Air conditioning

                                      Price per night from

                                      $390

                                      Price per night from

                                      $390

                                      (1) Excellent 

                                        32

                                        Apartment "Belvedere" at The House of the Oaks - Montepulciano

                                        Montepulciano / Acquaviva di Montepulciano

                                        Acquaviva di Montepulciano apartment

                                        1 4 min stay varies

                                        • 1 bedroom
                                        • sleeps 4
                                        • min stay varies
                                        • Nearest beach 130 mi
                                        • Swimming pool
                                        • Child Friendly

                                        Price per night from

                                        $104

                                        Responds fast!
                                        avg. 1 hour 58 minutes

                                        Price per night from

                                        $104

                                        (1) Excellent 

                                          20

                                          4 bedrooms in a tower, home of a sculptor

                                          Province of Siena / Montepulciano

                                          Montepulciano b and b

                                          4 8 2 nights min

                                          • 4 bedrooms
                                          • sleeps 8
                                          • 2 nights min
                                          • Swimming pool
                                          • Private garden

                                          Price per night from

                                          $430

                                          Responds fast!
                                          avg. 3 hours 30 minutes

                                          Price per night from

                                          $430

                                          (2) Very Good 

                                            14

                                            Agriturismo I Fuochi

                                            Montepulciano / Valiano

                                            Valiano farmhouse

                                            11 22 2 nights min

                                            • 11 bedrooms
                                            • sleeps 22
                                            • 2 nights min
                                            • Swimming pool
                                            • Child Friendly
                                            • Pet Friendly

                                            Price per night from

                                            $1,106

                                            Responds fast!
                                            avg. 3 hours 11 minutes

                                            Price per night from

                                            $1,106

                                            (24) Excellent 

                                              38

                                              CasaMontepulciano, In the heart of Montepulciano

                                              Province of Siena / Montepulciano

                                              Montepulciano apartment

                                              2 4 2 nights min

                                              • 2 bedrooms
                                              • sleeps 4
                                              • 2 nights min
                                              • Child Friendly
                                              • Air conditioning
                                              • Pet Friendly
                                              “Beautiful Montepulciano, Fantastic Host (Luca), Great apartment” We honestly cannot say enough good things about wonderful Luca and his beautiful place in Montepulciano. If you are thinking of staying in this delightful hill town (and it makes a great
                                              …see more

                                              Price per night from

                                              $137

                                              Responds fast!
                                              avg. 1 hour 11 minutes

                                              Price per night from

                                              $137

                                                28

                                                Luxury villa Vignola

                                                Province of Siena / Montepulciano

                                                Montepulciano villa

                                                7 19 7 nights min

                                                • 7 bedrooms
                                                • sleeps 19
                                                • 7 nights min
                                                • Swimming pool
                                                • Child Friendly
                                                • Air conditioning

                                                Price per night from

                                                $829

                                                Price per night from

                                                $829

                                                  30

                                                  Luxury villa Ivory

                                                  Montepulciano / Sant'Albino

                                                  Sant'Albino villa

                                                  8 16 7 nights min

                                                  • 8 bedrooms
                                                  • sleeps 16
                                                  • 7 nights min
                                                  • Swimming pool
                                                  • Child Friendly
                                                  • Air conditioning

                                                  Price per night from

                                                  $2,257

                                                  Price per night from

                                                  $2,257

                                                    24

                                                    Country House at Antico Podere in Montepulciano, Tuscany

                                                    Province of Siena / Montepulciano

                                                    Montepulciano apartment

                                                    1 2 1 night min

                                                    • 1 bedroom
                                                    • sleeps 2
                                                    • 1 night min
                                                    • Swimming pool
                                                    • Child Friendly
                                                    • Pet Friendly

                                                    Price per night from

                                                    $157

                                                    Price per night from

                                                    $157

                                                    (2) Excellent 

                                                      52

                                                      Rustic Stone Brick Villa on Siena Countryside

                                                      Province of Siena / Montepulciano

                                                      Montepulciano villa

                                                      7 16 7 nights min

                                                      • 7 bedrooms
                                                      • sleeps 16
                                                      • 7 nights min
                                                      • Ask about children
                                                      • Pet Friendly
                                                      “Splendid villa and great service!” Amazing place, absolutely fantastic holiday, real Tuscan atmosphere. This is a villa I would recommend to anybody and I hope to see myself visiting it again in the future. Great service and customer assistance by the
                                                      …see more

                                                      Price per night from

                                                      $520

                                                      Price per night from

                                                      $520

                                                        37

                                                        7 bedroom Villa in Castelluccio, Tuscany, Italy - 5247920

                                                        Montepulciano / Sant'Albino

                                                        Sant'Albino villa

                                                        7 14 7 nights min

                                                        • 7 bedrooms
                                                        • sleeps 14
                                                        • 7 nights min
                                                        • Swimming pool
                                                        • Child Friendly
                                                        • Ask about pets

                                                        Price per night from

                                                        $782

                                                        Price per night from

                                                        $782

                                                        (3) Very Good 

                                                          22

                                                          Villa Montepulciano

                                                          Province of Siena / Montepulciano

                                                          Montepulciano villa

                                                          6 15 7 nights min

                                                          • 6 bedrooms
                                                          • sleeps 15
                                                          • 7 nights min
                                                          • Ask about children
                                                          • Ask about pets
                                                          “Perfect...” Perfect Villa and setting to enjoy all the splendors that Tuscany and Montepulciano has to offer. - Rose L., ,
                                                          …see more

                                                          Price per night from

                                                          $908

                                                          Responds fast!
                                                          avg. 1 hour 5 minutes

                                                          Price per night from

                                                          $908

                                                          (2) Very Good 

                                                            55

                                                            Rustic Tuscan Farmhouse at Podere Pisinano

                                                            Province of Siena / Montepulciano

                                                            Montepulciano villa

                                                            4 10 7 nights min

                                                            • 4 bedrooms
                                                            • sleeps 10
                                                            • 7 nights min
                                                            • Ask about children
                                                            • Ask about pets

                                                            Price per night from

                                                            $455

                                                            Price per night from

                                                            $455

                                                              37

                                                              Villa Viole - Dream under the tuscan sun

                                                              Province of Siena / Montepulciano

                                                              Montepulciano apartment

                                                              2 4 3 nights min

                                                              • 2 bedrooms
                                                              • sleeps 4
                                                              • 3 nights min
                                                              • Swimming pool
                                                              • Child Friendly
                                                              • Air conditioning

                                                              Price per night from

                                                              $196

                                                              Price per night from

                                                              $196

                                                              (4) Excellent 

                                                                38

                                                                DOWNTOWN WITH A VIEW!Entire Home w. huge Terraces

                                                                Province of Siena / Montepulciano

                                                                Montepulciano house

                                                                4 10 2 nights min

                                                                • 4 bedrooms
                                                                • sleeps 10
                                                                • 2 nights min
                                                                • Nearest beach 41 mi
                                                                • Child Friendly
                                                                • Private garden

                                                                Price per night from

                                                                $201

                                                                Responds fast!
                                                                avg. 1 hour 45 minutes

                                                                Price per night from

                                                                $201

                                                                (1) Very Good 

                                                                  37

                                                                  Studio "Rustic" at The House of the Oaks - Montepulciano

                                                                  Montepulciano / Acquaviva di Montepulciano

                                                                  Acquaviva di Montepulciano apartment

                                                                  1 2 min stay varies

                                                                  • 1 bedroom
                                                                  • sleeps 2
                                                                  • min stay varies
                                                                  • Nearest beach 120 mi
                                                                  • Swimming pool
                                                                  • Child Friendly

                                                                  Price per night from

                                                                  $85

                                                                  Responds fast!
                                                                  avg. 1 hour 58 minutes

                                                                  Price per night from

                                                                  $85

                                                                  (19) Excellent 

                                                                    17

                                                                    Tuscan Tower - A unique castle apartment

                                                                    Province of Siena / Montepulciano

                                                                    Montepulciano apartment

                                                                    2 4 7 nights min

                                                                    • 2 bedrooms
                                                                    • sleeps 4
                                                                    • 7 nights min
                                                                    • Suitable for children age 5+
                                                                    “Great Place. Quiet town. Beautiful Views” Excellent location. Beautiful apartment. John and Wendy were great to work with. They provided ideas of where to visit and outlined helpful tips for the week we were there. I would highly recommend staying wi
                                                                    …see more

                                                                    Price per night from

                                                                    $298

                                                                    Price per night from

                                                                    $298

                                                                      11

                                                                      Beautiful apartment with pool in Montepulciano

                                                                      Montepulciano / Valiano

                                                                      Valiano apartment

                                                                      3 5 2 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 5
                                                                      • 2 nights min
                                                                      • Child Friendly
                                                                      • Pet Friendly

                                                                      Price per night from

                                                                      $222

                                                                      Responds fast!
                                                                      avg. 3 hours 11 minutes

                                                                      Price per night from

                                                                      $222

                                                                        39

                                                                        Apartment "Poggino" - Montepulciano

                                                                        Montepulciano / Acquaviva di Montepulciano

                                                                        Acquaviva di Montepulciano apartment

                                                                        2 4 min stay varies

                                                                        • 2 bedrooms
                                                                        • sleeps 4
                                                                        • min stay varies
                                                                        • Nearest beach 120 mi
                                                                        • Swimming pool
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $117

                                                                        Responds fast!
                                                                        avg. 1 hour 58 minutes

                                                                        Price per night from

                                                                        $117

                                                                        (2) Excellent 

                                                                          39

                                                                          Tigli #3, 2 bedrooms and 2 bathrooms apt close Montepulciano. Wi-Fi, A/C & pool

                                                                          Province of Siena / Montepulciano

                                                                          Montepulciano apartment

                                                                          2 6 min stay varies

                                                                          • 2 bedrooms
                                                                          • sleeps 6
                                                                          • min stay varies
                                                                          • Nearest beach 185 mi
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          “Excellent apartments in a gorgeous location” I stayed with my family and another family for a week in apartments #1 and #3. The couple managing the compound are very nice and helpful, but also very strict and professional about the rules concerning pa
                                                                          …see more

                                                                          Price per night from

                                                                          $133

                                                                          Price per night from

                                                                          $133

                                                                          (1) Excellent 

                                                                            51

                                                                            The Molinaccio 10 + 2

                                                                            Montepulciano / Acquaviva di Montepulciano

                                                                            Acquaviva di Montepulciano villa

                                                                            5 12 7 nights min

                                                                            • 5 bedrooms
                                                                            • sleeps 12
                                                                            • 7 nights min
                                                                            • Ask about children
                                                                            • Pet Friendly

                                                                            Price per night from

                                                                            $428

                                                                            Price per night from

                                                                            $428

                                                                            (1) Very Good 

                                                                              42

                                                                              "Policiano Suite" at The House of the Oaks - Montepulciano

                                                                              Montepulciano / Acquaviva di Montepulciano

                                                                              Acquaviva di Montepulciano apartment

                                                                              2 6 min stay varies

                                                                              • 2 bedrooms
                                                                              • sleeps 6
                                                                              • min stay varies
                                                                              • Nearest beach 120 mi
                                                                              • Swimming pool
                                                                              • Child Friendly

                                                                              Price per night from

                                                                              $196

                                                                              Responds fast!
                                                                              avg. 1 hour 58 minutes

                                                                              Price per night from

                                                                              $196

                                                                              About Montepulciano

                                                                              Montepulciano is a beautiful village in a hilly area of Tuscany overlooking the Valdichiana countryside. The streets here leave a lasting impression on visitors because of their old world charm and also because of their steep inclines, which can make an adventure out of an ordinary day spent exploring markets and relaxing in cafes.

                                                                              These sloping streets wind among some unforgettable restaurants and wine cellars. They can also take you to some of the most beautiful renaissance churches in Tuscany. Head beyond the center of town and take a hike through the rolling countryside of world famous vineyards and olive groves. At the end of the day, head back to experience the delicious cuisine that brings knowledgeable foodies to Montepulciano from all over the world and enjoy a glass of vino nobile as the sun sets.

                                                                              Here are a few additional suggestions as you plan your trip:

                                                                              • Visit the Chiesa di San Biagio: This domed renaissance church with its fantastic marble alter piece lies in a valley just to the west of the Chiesa del Gesu, another impressive work of religious architecture.
                                                                              • Explore the Museo Civico: The town of Montepulciano has its own civic museum, which houses artifacts documenting its long history.
                                                                              • Explore the cantinas of Montepulciano: Tuscany is known for its wine, but Montepulciano in particular has a charming community of cantinas that offer tours through cellars packed with casks followed by a unique tasting experience.
                                                                              • Take a tour of the Azienda Agricola Canneto: This sprawling vineyard close to the Church of San Biagio produces regional vino nobile and extra virgin olive oil. Come to tour the grounds and learn more about how these precious items are produced.
                                                                              • Take an Italian cooking class: Sample the unforgettable flavors of Tuscany at the restaurants and trattorias of Montepulciano, then take a course from a skilled chef and learn how to bring these flavors home with you.
                                                                              • Visit the Formaggi Cugusi Silvana: The family that runs this artisanal pecorino cheese shop makes cheese with the milk from their own sheep that graze in the pastures of the Val d'Orcia.

                                                                              You'll have no trouble finding world class dining opportunities, and you'll also have no trouble finding a vacation rental that offers luxurious views of the Tuscan countryside. Find an elegant condo downtown or a beautiful rustic villa overlooking the vineyards. While you're visiting Montepulciano, you may want to include a day trip to the beautiful town of Torrita di Siena in your plans.