Vacation Rentals & Villas in Pienza

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3,336 Houses

(2) Very Good 

    13

    2 Bedroom Vacation Apartment with Antique Charm

    Province of Siena / Pienza

    Pienza apartment

    2 4 1 night min

    • 2 bedrooms
    • sleeps 4
    • 1 night min
    • Nearest beach 90 mi
    • Child Friendly
    • Air conditioning
    “Perfect, charming, peaceful apartment in a stunning area” This apartment has all the conveniences and is situated in the beautiful small village of Monticchiello overlooking the Val d'Orcia. Comfortable beds, nicely equipped kitchen, thoughtfully appo

    Price per night from

    $104

    Price per night from

    $104

      19

      Accommodation near Pienza Tuscany

      Province of Siena / Pienza

      Pienza apartment

      3 6 2 nights min

      • 3 bedrooms
      • sleeps 6
      • 2 nights min
      • Child Friendly
      • Ask about pets

      Price per night from

      $233

      Price per night from

      $233

      (3) Very Good 

        8

        Secret Tuscany property

        Pienza / Monticchiello

        Monticchiello apartment

        2 3 1 night min

        • 2 bedrooms
        • sleeps 3
        • 1 night min
        • Nearest beach 90 mi
        • Child Friendly
        • Pet Friendly

        Price per night from

        $129

        Price per night from

        $129

          36

          Podere Osteria

          Province of Siena / Pienza

          Pienza apartment

          4 8 7 nights min

          • 4 bedrooms
          • sleeps 8
          • 7 nights min
          • Swimming pool
          • Child Friendly

          Price per night from

          $256

          Price per night from

          $256

          (1) Excellent 

            15

            Villa Four Seasons

            Province of Siena / Pienza

            Pienza house

            4 8 7 nights min

            • 4 bedrooms
            • sleeps 8
            • 7 nights min
            • Swimming pool
            • Ask about children
            • Ask about pets
            “Beautiful and relaxing” My husband and I stayed at La Terrazza for 5 days in June 2011, along with our children aged 11 and 15. We loved the apartment - especially al fresco dining on the balcony overlooking the pool. We loved walking down into the sm

            Price per night from

            $256

            Price per night from

            $256

              23

              8 bedroom Villa with Pool, Air Con and WiFi - 5049085

              Province of Siena / Pienza

              Pienza villa

              8 15 7 nights min

              • 8 bedrooms
              • sleeps 15
              • 7 nights min
              • Swimming pool
              • Child Friendly
              • Air conditioning

              Price per night from

              $1,386

              Price per night from

              $1,386

                27

                Quiet farmhouse

                Province of Siena / Pienza

                Pienza villa

                6 12 min stay varies

                • 6 bedrooms
                • sleeps 12
                • min stay varies
                • Child Friendly
                • Ask about pets

                Price per night from

                $1,211

                Price per night from

                $1,211

                (1) Excellent 

                  45

                  Villa Pienza

                  Province of Siena / Pienza

                  Pienza villa

                  6 12 7 nights min

                  • 6 bedrooms
                  • sleeps 12
                  • 7 nights min
                  • Swimming pool
                  • Ask about children
                  • Air conditioning

                  Price per night from

                  $1,126

                  Responds fast!
                  avg. 3 hours 7 minutes

                  Price per night from

                  $1,126

                    20

                    3 bedroom Villa with Pool and WiFi - 5247826

                    Province of Siena / Pienza

                    Pienza villa

                    5 8 7 nights min

                    • 5 bedrooms
                    • sleeps 8
                    • 7 nights min
                    • Swimming pool
                    • Child Friendly
                    • Ask about pets

                    Price per night from

                    $201

                    Price per night from

                    $201

                    (1) Very Good 

                      47

                      Villa in Southern Tuscany with Privacy and Views - Villa Altare

                      Province of Siena / Pienza

                      Pienza house

                      7 14 7 nights min

                      • 7 bedrooms
                      • sleeps 14
                      • 7 nights min
                      • Swimming pool
                      • Ask about children
                      • Pet Friendly
                      “Bill's review of Villa Altare” Very good. Spacious and private. We had several chefs come to prepare meals. We walked into the town of Monticchiello. Other local towns were also great.

                      Price per night from

                      $1,200

                      Price per night from

                      $1,200

                        29

                        Country farmhouse

                        Province of Siena / Pienza

                        Pienza villa

                        8 14 min stay varies

                        • 8 bedrooms
                        • sleeps 14
                        • min stay varies
                        • Child Friendly
                        • Ask about pets

                        Price per night from

                        $1,215

                        Price per night from

                        $1,215

                          49

                          Inviting Tuscan Farmhouse with Incredible Views and Privacy - Casale Pienza

                          Province of Siena / Pienza

                          Pienza house

                          7 14 7 nights min

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

                          Price per night from

                          $1,400

                          Price per night from

                          $1,400

                            25

                            7 bedroom Villa with Pool, Air Con and WiFi - 5247844

                            Pienza / Monticchiello

                            Monticchiello villa

                            7 14 7 nights min

                            • 7 bedrooms
                            • sleeps 14
                            • 7 nights min
                            • Swimming pool
                            • Child Friendly
                            • Air conditioning

                            Price per night from

                            $1,068

                            Price per night from

                            $1,068

                              38

                              8 bedroom Villa with Pool, Air Con and WiFi - 5247816

                              Province of Siena / Pienza

                              Pienza villa

                              8 16 7 nights min

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

                              Price per night from

                              $1,420

                              Price per night from

                              $1,420

                                20

                                Villa Saffron holiday vacation villa rental italy, tuscany, pienza, near florenc

                                Province of Siena / Pienza

                                Pienza house

                                2 4 7 nights min

                                • 2 bedrooms
                                • sleeps 4
                                • 7 nights min
                                • Ask about children
                                • Pet Friendly

                                Price per night from

                                $224

                                Price per night from

                                $224

                                  50

                                  8 bedroom Villa with Pool, Air Con and WiFi - 5433051

                                  Pienza / Monticchiello

                                  Monticchiello villa

                                  8 12 7 nights min

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

                                  Price per night from

                                  $1,196

                                  Price per night from

                                  $1,196

                                    20

                                    Villa Ilario vacation holiday villa rental italy, tuscany, siena, pool, view, va

                                    Province of Siena / Pienza

                                    Pienza house

                                    5 10 7 nights min

                                    • 5 bedrooms
                                    • sleeps 10
                                    • 7 nights min
                                    • Ask about children
                                    • Pet Friendly

                                    Price per night from

                                    $428

                                    Price per night from

                                    $428

                                      27

                                      6 bedroom Villa with Pool and WiFi - 5218303

                                      Province of Siena / Pienza

                                      Pienza villa

                                      6 11 7 nights min

                                      • 6 bedrooms
                                      • sleeps 11
                                      • 7 nights min
                                      • Swimming pool
                                      • Child Friendly
                                      • Ask about pets

                                      Price per night from

                                      $879

                                      Price per night from

                                      $879

                                        80

                                        7 bedroom Villa with Pool and WiFi - 5763498

                                        Province of Siena / Pienza

                                        Pienza villa

                                        7 14 7 nights min

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

                                        Price per night from

                                        $1,070

                                        Price per night from

                                        $1,070

                                          34

                                          7 bedroom Villa with Pool and WiFi - 5490495

                                          Province of Siena / Pienza

                                          Pienza villa

                                          7 13 7 nights min

                                          • 7 bedrooms
                                          • sleeps 13
                                          • 7 nights min
                                          • Swimming pool
                                          • Child Friendly
                                          • Pet Friendly

                                          Price per night from

                                          $342

                                          Price per night from

                                          $342

                                            62

                                            The Cipressini 10

                                            Province of Siena / Pienza

                                            Pienza villa

                                            5 10 7 nights min

                                            • 5 bedrooms
                                            • sleeps 10
                                            • 7 nights min
                                            • Ask about children
                                            • Air conditioning
                                            • Pet Friendly

                                            Price per night from

                                            $515

                                            Price per night from

                                            $515

                                              31

                                              Tuscan Farmhouse with Private Pool and Beautiful Views - Villa Gaia

                                              Pienza / Monticchiello

                                              Monticchiello farmhouse

                                              12 7 nights min

                                              • sleeps 12
                                              • 7 nights min
                                              • Swimming pool
                                              • Ask about children
                                              • Ask about pets

                                              Price per night from

                                              $840

                                              Price per night from

                                              $840

                                              (1) Excellent 

                                                20

                                                Villa Pienza Large Italian villa rental in Pienza near Siena - Tuscany

                                                Province of Siena / Pienza

                                                Pienza house

                                                6 12 7 nights min

                                                • 6 bedrooms
                                                • sleeps 12
                                                • 7 nights min
                                                • Ask about children
                                                • Air conditioning
                                                • Pet Friendly

                                                Price per night from

                                                $1,115

                                                Price per night from

                                                $1,115

                                                  22

                                                  5 bedroom Villa with Pool and WiFi - 5763491

                                                  Province of Siena / Pienza

                                                  Pienza villa

                                                  5 10 7 nights min

                                                  • 5 bedrooms
                                                  • sleeps 10
                                                  • 7 nights min
                                                  • Swimming pool
                                                  • Child Friendly
                                                  • Ask about pets

                                                  Price per night from

                                                  $868

                                                  Price per night from

                                                  $868

                                                    20

                                                    Villa Chiara holiday vacation villa rental italy, tuscany, pienza, holiday vacat

                                                    Province of Siena / Pienza

                                                    Pienza house

                                                    8 14 7 nights min

                                                    • 8 bedrooms
                                                    • sleeps 14
                                                    • 7 nights min
                                                    • Ask about children
                                                    • Air conditioning
                                                    • Pet Friendly

                                                    Price per night from

                                                    $1,084

                                                    Price per night from

                                                    $1,084

                                                      20

                                                      Villa Rosina holiday vacation large villa rental italy, tuscany, pienza, siena,

                                                      Province of Siena / Pienza

                                                      Pienza house

                                                      6 12 7 nights min

                                                      • 6 bedrooms
                                                      • sleeps 12
                                                      • 7 nights min
                                                      • Ask about children
                                                      • Air conditioning
                                                      • Pet Friendly

                                                      Price per night from

                                                      $542

                                                      Price per night from

                                                      $542

                                                        32

                                                        9 bedroom Villa with Pool and WiFi - 5764394

                                                        Pienza / Monticchiello

                                                        Monticchiello villa

                                                        9 20 7 nights min

                                                        • 9 bedrooms
                                                        • sleeps 20
                                                        • 7 nights min
                                                        • Swimming pool
                                                        • Child Friendly
                                                        • Ask about pets

                                                        Price per night from

                                                        $1,197

                                                        Price per night from

                                                        $1,197

                                                          20

                                                          Villa Cappelli holiday vacation large villa rental italy, tuscany, near siena, p

                                                          Pienza / Monticchiello

                                                          Monticchiello house

                                                          6 12 7 nights min

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

                                                          Price per night from

                                                          $956

                                                          Price per night from

                                                          $956

                                                            27

                                                            4 bedroom Villa with Pool and WiFi - 5218323

                                                            Province of Siena / Pienza

                                                            Pienza villa

                                                            4 7 7 nights min

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

                                                            Price per night from

                                                            $592

                                                            Price per night from

                                                            $592

                                                              29

                                                              7 bedroom Villa with Pool and WiFi - 5763495

                                                              Province of Siena / Pienza

                                                              Pienza villa

                                                              7 14 7 nights min

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

                                                              Price per night from

                                                              $1,312

                                                              Price per night from

                                                              $1,312

                                                                20

                                                                Villa Pamina holiday vacation large villa rental italy, tuscany, near siena, pie

                                                                Pienza / Monticchiello

                                                                Monticchiello house

                                                                7 14 7 nights min

                                                                • 7 bedrooms
                                                                • sleeps 14
                                                                • 7 nights min
                                                                • Ask about children
                                                                • Air conditioning
                                                                • Pet Friendly

                                                                Price per night from

                                                                $1,030

                                                                Price per night from

                                                                $1,030

                                                                  11

                                                                  Villa Vittoria nestled in the heart of Val d'Orcia

                                                                  Province of Siena / Pienza

                                                                  Pienza villa

                                                                  11 24 7 nights min

                                                                  • 11 bedrooms
                                                                  • sleeps 24
                                                                  • 7 nights min
                                                                  • Child Friendly
                                                                  • Pet Friendly

                                                                  Price per night from

                                                                  $1,033

                                                                  Price per night from

                                                                  $1,033

                                                                  (1)  

                                                                    14

                                                                    Maribelle 3

                                                                    Pienza / Monticchiello

                                                                    Monticchiello villa

                                                                    2 5 1 night min

                                                                    • 2 bedrooms
                                                                    • sleeps 5
                                                                    • 1 night min
                                                                    • Nearest beach 90 mi
                                                                    • Air conditioning
                                                                    • Private garden

                                                                    Price per night from

                                                                    $194

                                                                    Price per night from

                                                                    $194

                                                                      24

                                                                      4 bedroom Villa with Pool and WiFi - 5247845

                                                                      Pienza / Monticchiello

                                                                      Monticchiello villa

                                                                      4 8 7 nights min

                                                                      • 4 bedrooms
                                                                      • sleeps 8
                                                                      • 7 nights min
                                                                      • Swimming pool
                                                                      • Child Friendly
                                                                      • Ask about pets

                                                                      Price per night from

                                                                      $286

                                                                      Price per night from

                                                                      $286

                                                                        33

                                                                        Luxury villa Cecoro

                                                                        Province of Siena / Pienza

                                                                        Pienza villa

                                                                        6 12 7 nights min

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

                                                                        Price per night from

                                                                        $2,191

                                                                        Price per night from

                                                                        $2,191

                                                                          19

                                                                          4 bedroom Villa with Pool - 5656179

                                                                          Pienza / Monticchiello

                                                                          Monticchiello apartment

                                                                          4 10 7 nights min

                                                                          • 4 bedrooms
                                                                          • sleeps 10
                                                                          • 7 nights min
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Pet Friendly

                                                                          Price per night from

                                                                          $148

                                                                          Price per night from

                                                                          $148

                                                                          (1) Excellent 

                                                                            29

                                                                            Tuscan Farmhouse with a Private Pool Near Spas - Villa Vigna

                                                                            Pienza / Monticchiello

                                                                            Monticchiello farmhouse

                                                                            4 8 7 nights min

                                                                            • 4 bedrooms
                                                                            • sleeps 8
                                                                            • 7 nights min
                                                                            • Swimming pool
                                                                            • Ask about children
                                                                            • Ask about pets

                                                                            Price per night from

                                                                            $500

                                                                            Price per night from

                                                                            $500

                                                                              25

                                                                              6 bedroom Villa with Pool and WiFi - 5049046

                                                                              Pienza / Monticchiello

                                                                              Monticchiello villa

                                                                              6 12 7 nights min

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

                                                                              Price per night from

                                                                              $802

                                                                              Price per night from

                                                                              $802