Castellina In Chianti Rentals

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6,364 Houses

    17

    Cottage in Chianti, with pool, spa, and wonderview

    Province of Siena / Castellina In Chianti

    Castellina In Chianti cottage

    2 5 7 nights min

    • 2 bedrooms
    • sleeps 5
    • 7 nights min
    • Nearest beach 97 mi
    • Swimming pool
    • Child Friendly

    Price per night from

    $173

    Price per night from

    $173

    (46) Excellent 

      31

      La Tinaia, Podere Patrignone - a Tuscan cottage with garden, views and pool

      Province of Siena / Castellina In Chianti

      Castellina In Chianti cottage

      1 2 min stay varies

      • 1 bedroom
      • sleeps 2
      • min stay varies
      • Nearest beach 60 mi
      • Swimming pool
      • Child Friendly
      “Very Romantic and Relaxing” Podere Patrignone, is a very well managed holiday/vacation destination. Simon and Verity (owners), went to great lengths to make sure ours and other guests stays we're relaxing and enjoyable. Always available, but rairly

      Price per night from

      $192

      Price per night from

      $192

        16

        Rental house in the centre of this Chianti village

        Province of Siena / Castellina In Chianti

        Castellina In Chianti apartment

        2 5 1 night min

        • 2 bedrooms
        • sleeps 5
        • 1 night min
        • Child Friendly

        Price per night from

        $90

        Price per night from

        $90

        (3) Excellent 

          13

          Lovely apartment in a small winery

          Province of Siena / Castellina In Chianti

          Castellina In Chianti barn

          2 4 7 nights min

          • 2 bedrooms
          • sleeps 4
          • 7 nights min
          • Swimming pool
          • Child Friendly
          • Air conditioning
          “The real heart of Tuscany, a dreamholiday” For many years we have spent every summerholiday in Italy. It took only little time trying out various locations before we realized that the Casina at Setriolo was the perfect place and since then we haven't

          Price per night from

          $146

          Price per night from

          $146

          (3) Average 

            19

            Ancient villa in Chianti with pool and wonderview

            Province of Siena / Castellina In Chianti

            Castellina In Chianti villa

            3 6 7 nights min

            • 3 bedrooms
            • sleeps 6
            • 7 nights min
            • Nearest beach 97 mi
            • Swimming pool
            • Child Friendly

            Price per night from

            $236

            Price per night from

            $236

              23

              CASALTA DI PESA VIRGO apartment

              Province of Siena / Castellina In Chianti

              Castellina In Chianti house

              2 4 3 nights min

              • 2 bedrooms
              • sleeps 4
              • 3 nights min
              • Nearest beach 90 mi
              • Swimming pool
              • Child Friendly

              Price per night from

              $192

              Price per night from

              $192

                16

                Guidi

                Province of Siena / Castellina In Chianti

                Castellina In Chianti apartment

                2 4 7 nights min

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

                Price per night from

                $92

                Price per night from

                $92

                  59

                  3 bedroom Villa with Pool and WiFi - 5228944

                  Province of Siena / Castellina In Chianti

                  Castellina In Chianti villa

                  3 6 7 nights min

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

                  Price per night from

                  $237

                  Price per night from

                  $237

                    31

                    ANDROMEDA Villa - CASALTADIPESA com

                    Province of Siena / Castellina In Chianti

                    Castellina In Chianti house

                    2 5 3 nights min

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

                    Price per night from

                    $231

                    Price per night from

                    $231

                      25

                      CASALTA DI PESA - LYRA apartment

                      Province of Siena / Castellina In Chianti

                      Castellina In Chianti house

                      2 4 3 nights min

                      • 2 bedrooms
                      • sleeps 4
                      • 3 nights min
                      • Nearest beach 90 mi
                      • Swimming pool
                      • Child Friendly

                      Price per night from

                      $179

                      Price per night from

                      $179

                      (8) Excellent 

                        30

                        Authentic 3 Bedroom Farmhouse

                        Province of Siena / Castellina In Chianti

                        Castellina In Chianti b&b

                        3 8 min stay varies

                        • 3 bedrooms
                        • sleeps 8
                        • min stay varies
                        • Swimming pool
                        • Child Friendly
                        • Car not necessary
                        “The best and most relaxing vacation ever” As two couples, Poderi Val Verde's restored farmhouse was indeed rustic, but was perfect for us: adjoining suites each with a kitchen and patio overlooking the stunning grounds, one with a living room and fire

                        Price per night from

                        $298

                        Price per night from

                        $298

                          33

                          CASALTA DI PESA - CASSIOPEA apartment

                          Province of Siena / Castellina In Chianti

                          Castellina In Chianti house

                          3 6 3 nights min

                          • 3 bedrooms
                          • sleeps 6
                          • 3 nights min
                          • Swimming pool
                          • Child Friendly

                          Price per night from

                          $192

                          Price per night from

                          $192

                            38

                            House Belmonte

                            Province of Siena / Castellina In Chianti

                            Castellina In Chianti house

                            4 8 7 nights min

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

                            Price per night from

                            $247

                            Price per night from

                            $247

                            (17) Excellent 

                              30

                              2 Bedroom Cottage in Castellina in Chianti

                              Province of Siena / Castellina In Chianti

                              Castellina In Chianti cottage

                              2 6 7 nights min

                              • 2 bedrooms
                              • sleeps 6
                              • 7 nights min
                              • Nearest beach 100 mi
                              • Swimming pool
                              • Child Friendly
                              “Homely days in Chianti” Very nice location - quiet and ideal for relaxation - polite hostess - tasteful furnished old stone house with modern comfort in kitchen and bathroom - wonderful situated (all the beautiful spots in Chianti are nearby). We woul

                              Price per night from

                              $201

                              Price per night from

                              $201

                              (10) Excellent 

                                19

                                3BR/3BA apartment on Tuscan Estate in the Chianti

                                Province of Siena / Castellina In Chianti

                                Castellina In Chianti apartment

                                3 9 min stay varies

                                • 3 bedrooms
                                • sleeps 9
                                • min stay varies
                                • Swimming pool
                                • Child Friendly
                                • Air conditioning
                                “Lovely home cooking courses” My wife and I came to Chianti for our honeymoon, and spent a thoroughly enjoyable evening doing a cookery course with Ulrike. The meals were traditional Tuscan fare and delicious, whilst easy enough to follow so that we w

                                Price per night from

                                $261

                                Price per night from

                                $261

                                (1) Excellent 

                                  59

                                  Villa Delle Upupe 8

                                  Province of Siena / Castellina In Chianti

                                  Castellina In Chianti villa

                                  4 8 7 nights min

                                  • 4 bedrooms
                                  • sleeps 8
                                  • 7 nights min
                                  • Ask about children
                                  • Pet Friendly

                                  Price per night from

                                  $568

                                  Price per night from

                                  $568

                                  (7) Excellent 

                                    25

                                    2BR /1BA apartment

                                    Province of Siena / Castellina In Chianti

                                    Castellina In Chianti farmhouse

                                    2 4 7 nights min

                                    • 2 bedrooms
                                    • sleeps 4
                                    • 7 nights min
                                    • Nearest beach 113 mi
                                    • Swimming pool
                                    • Child Friendly
                                    “Location, location, location!” The complete Chianti valley, rustica experience of staying in comfortable stone cottages surrounded by beautiful gardens - the irises were blooming while we were there - plenty of space for kids to run and play while the

                                    Price per night from

                                    $153

                                    Price per night from

                                    $153

                                      27

                                      Tuscany Apartment in Old Chianti Farmhouse

                                      Province of Siena / Castellina In Chianti

                                      Castellina In Chianti apartment

                                      2 8 5 nights min

                                      • 2 bedrooms
                                      • sleeps 8
                                      • 5 nights min
                                      • Child Friendly

                                      Price per night from

                                      $145

                                      Price per night from

                                      $145

                                      (36) Excellent 

                                        30

                                        Beautiful 2-bedroom apartment villa in the heart of Chianti, pool & sunset views

                                        Province of Siena / Castellina In Chianti

                                        Castellina In Chianti apartment

                                        2 4 min stay varies

                                        • 2 bedrooms
                                        • sleeps 4
                                        • min stay varies
                                        • Nearest beach 60 mi
                                        • Swimming pool
                                        • Child Friendly
                                        “A totally relaxing rural Tuscan retreat.” Podere Patrignone is a beautifully rustic, rambling farmhouse, secluded in its own woods. There are a number of properties for rent within the complex, from compact and bijou, to spacious and open, all with th

                                        Price per night from

                                        $282

                                        Price per night from

                                        $282

                                        (8) Excellent 

                                          19

                                          2 Bedroom Stone Cottage Rental in Chianti Countryside

                                          Province of Siena / Castellina In Chianti

                                          Castellina In Chianti cottage

                                          2 4 min stay varies

                                          • 2 bedrooms
                                          • sleeps 4
                                          • min stay varies
                                          • Child Friendly
                                          • Pet Friendly
                                          “Beautiful” We had a excellent stay. It was very clean, comfotable and beautifull.

                                          Price per night from

                                          $135

                                          Price per night from

                                          $135

                                            16

                                            Luxury 2 bedroom Tuscan Villa

                                            Province of Siena / Castellina In Chianti

                                            Castellina In Chianti house

                                            2 4 min stay varies

                                            • 2 bedrooms
                                            • sleeps 4
                                            • min stay varies
                                            • Swimming pool
                                            • Child Friendly

                                            Price per night from

                                            $248

                                            Price per night from

                                            $248

                                              17

                                              2 bedroom Villa with Pool and WiFi - 5247827

                                              Province of Siena / Castellina In Chianti

                                              Castellina In Chianti villa

                                              2 4 7 nights min

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

                                              Price per night from

                                              $222

                                              Price per night from

                                              $222

                                                23

                                                humiliated

                                                Province of Siena / Castellina In Chianti

                                                Castellina In Chianti house

                                                5 9 7 nights min

                                                • 5 bedrooms
                                                • sleeps 9
                                                • 7 nights min
                                                • Swimming pool
                                                • Child Friendly

                                                Price per night from

                                                $207

                                                Price per night from

                                                $207

                                                  68

                                                  Villa Beba 6

                                                  Province of Siena / Castellina In Chianti

                                                  Castellina In Chianti villa

                                                  3 6 7 nights min

                                                  • 3 bedrooms
                                                  • sleeps 6
                                                  • 7 nights min
                                                  • Swimming pool
                                                  • Child Friendly

                                                  Price per night from

                                                  $232

                                                  Price per night from

                                                  $232

                                                    19

                                                    Carraretto

                                                    Province of Siena / Castellina In Chianti

                                                    Castellina In Chianti apartment

                                                    3 6 7 nights min

                                                    • 3 bedrooms
                                                    • sleeps 6
                                                    • 7 nights min
                                                    • Swimming pool
                                                    • Child Friendly

                                                    Price per night from

                                                    $138

                                                    Price per night from

                                                    $138

                                                      29

                                                      Podere Patrignone - large private Chianti estate

                                                      Province of Siena / Castellina In Chianti

                                                      Castellina In Chianti villa

                                                      15 33 min stay varies

                                                      • 15 bedrooms
                                                      • sleeps 33
                                                      • min stay varies
                                                      • Nearest beach 60 mi
                                                      • Swimming pool
                                                      • Child Friendly

                                                      Price per night from

                                                      $1,625

                                                      Price per night from

                                                      $1,625

                                                      (26) Excellent 

                                                        38

                                                        Villa Patrignone - a beautiful large Tuscany Villa

                                                        Province of Siena / Castellina In Chianti

                                                        Castellina In Chianti villa

                                                        7 14 min stay varies

                                                        • 7 bedrooms
                                                        • sleeps 14
                                                        • min stay varies
                                                        • Nearest beach 60 mi
                                                        • Swimming pool
                                                        • Child Friendly
                                                        “Outstanding Tuscany Villa” We stayed at Podere Patrignone for 7 days in October 2012. We were a party of 4 couples from the USa. We had done a lot of research in finding a villa that would provide what we thought would be the ultimate Tuscan experienc

                                                        Price per night from

                                                        $583

                                                        Price per night from

                                                        $583

                                                          42

                                                          4 bedroom Villa with Pool and WiFi - 5637243

                                                          Castellina In Chianti / Fonterutoli

                                                          Fonterutoli villa

                                                          4 8 7 nights min

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

                                                          Price per night from

                                                          $275

                                                          Price per night from

                                                          $275

                                                            22

                                                            Fontani

                                                            Province of Siena / Castellina In Chianti

                                                            Castellina In Chianti house

                                                            4 7 7 nights min

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

                                                            Price per night from

                                                            $145

                                                            Price per night from

                                                            $145

                                                              19

                                                              5 bedroom Apartment with Pool, Air Con and WiFi - 5447418

                                                              Province of Siena / Castellina In Chianti

                                                              Castellina In Chianti apartment

                                                              5 9 7 nights min

                                                              • 5 bedrooms
                                                              • sleeps 9
                                                              • 7 nights min
                                                              • Swimming pool
                                                              • Child Friendly
                                                              • Air conditioning

                                                              Price per night from

                                                              $185

                                                              Price per night from

                                                              $185

                                                                17

                                                                Visentini

                                                                Province of Siena / Castellina In Chianti

                                                                Castellina In Chianti apartment

                                                                1 2 7 nights min

                                                                • 1 bedroom
                                                                • sleeps 2
                                                                • 7 nights min
                                                                • Swimming pool
                                                                • Child Friendly

                                                                Price per night from

                                                                $46

                                                                Price per night from

                                                                $46

                                                                  17

                                                                  Braccagni

                                                                  Province of Siena / Castellina In Chianti

                                                                  Castellina In Chianti apartment

                                                                  4 8 7 nights min

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

                                                                  Price per night from

                                                                  $165

                                                                  Price per night from

                                                                  $165

                                                                    19

                                                                    3 bedroom Apartment with Pool and WiFi - 5447419

                                                                    Province of Siena / Castellina In Chianti

                                                                    Castellina In Chianti apartment

                                                                    3 8 7 nights min

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

                                                                    Price per night from

                                                                    $168

                                                                    Price per night from

                                                                    $168

                                                                      25

                                                                      Spazzavento

                                                                      Province of Siena / Castellina In Chianti

                                                                      Castellina In Chianti house

                                                                      4 8 7 nights min

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

                                                                      Price per night from

                                                                      $183

                                                                      Price per night from

                                                                      $183

                                                                        12

                                                                        Castellina in Chianti 2 bed apartment with pool

                                                                        Province of Siena / Castellina In Chianti

                                                                        Castellina In Chianti apartment

                                                                        2 5 min stay varies

                                                                        • 2 bedrooms
                                                                        • sleeps 5
                                                                        • min stay varies
                                                                        • Swimming pool
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $280

                                                                        Price per night from

                                                                        $280

                                                                          26

                                                                          3 bedroom Apartment with Pool and WiFi - 5447429

                                                                          Province of Siena / Castellina In Chianti

                                                                          Castellina In Chianti apartment

                                                                          3 6 7 nights min

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

                                                                          Price per night from

                                                                          $152

                                                                          Price per night from

                                                                          $152

                                                                            43

                                                                            Sandonatino farmhouse

                                                                            Province of Siena / Castellina In Chianti

                                                                            Castellina In Chianti villa

                                                                            6 12 min stay varies

                                                                            • 6 bedrooms
                                                                            • sleeps 12
                                                                            • min stay varies
                                                                            • Swimming pool
                                                                            • Child Friendly

                                                                            Price per night from

                                                                            $457

                                                                            Price per night from

                                                                            $457

                                                                              23

                                                                              5 bedroom Villa with Pool, Air Con and WiFi - 5218299

                                                                              Province of Siena / Castellina In Chianti

                                                                              Castellina In Chianti villa

                                                                              5 10 7 nights min

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

                                                                              Price per night from

                                                                              $460

                                                                              Price per night from

                                                                              $460