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4,367 Houses

    56

    Ortensia - Ventena Vecchia Antico Frantoio

    Montevarchi / Chianti

    Chianti apartment

    1 4 3 nights min

    • 1 bedroom
    • sleeps 4
    • 3 nights min
    • Nearest beach 140 mi
    • Swimming pool
    • Child Friendly

    Price per night from

    $144

    Price per night from

    $144

    Great rentals within 20 miles that match your search

    Distance approx 10.18 km from Chianti Show on Map

    (23) Excellent 

      20

      Chianti Luxury Suite, Radda in Chianti - Siena

      Province of Siena / Radda in Chianti

      Radda in Chianti house

      1 2 4 nights min

      • 1 bedroom
      • sleeps 2
      • 4 nights min
      • Nearest beach 129 mi
      • Swimming pool
      • Ask about children
      “Dreams do come true in Radda” We spent a month in Europe and Radda was the last leg of our journey and the absolute best part of our trip. Besides the breath taking vistas that abound in all directions, the accommodations are spectacular. A comfor
      …see more

      Price per night from

      $350

      Price per night from

      $350

      Distance approx 13.29 km from Chianti

      (3) Very Good 

        18

        Sunny Apt.in the heart of Chianti !

        Province of Florence / Greve in Chianti

        Greve in Chianti apartment

        1 4 2 nights min

        • 1 bedroom
        • sleeps 4
        • 2 nights min
        • Child Friendly
        • Car not necessary
        • Pet Friendly

        Price per night from

        $107

        Price per night from

        $107

        Distance approx 3.81 km from Chianti Show on Map

          20

          Siena House, Residence in Tuscany, Farm Holiday

          Province of Arezzo / Pergine Valdarno

          Pergine Valdarno apartment

          2 5 2 nights min

          • 2 bedrooms
          • sleeps 5
          • 2 nights min
          • Nearest beach 130 mi
          • Swimming pool
          • Child Friendly

          Price per night from

          $91

          Price per night from

          $91

          Distance approx 17.32 km from Chianti

          (1) Excellent 

            90

            Typical house in Chianti

            Province of Florence / San Casciano in Val di Pesa

            San Casciano in Val di Pesa house

            3 6 3 nights min

            • 3 bedrooms
            • sleeps 6
            • 3 nights min
            • Nearest beach 161 mi
            • Child Friendly
            • Ask about pets

            Price per night from

            $156

            Price per night from

            $156

            Distance approx 17.69 km from Chianti

            (3) Very Good 

              8

              Santa Caterina Bed and Breakfast

              Province of Siena / Monteriggioni

              Monteriggioni b and b

              3 6 1 night min

              • 3 bedrooms
              • sleeps 6
              • 1 night min

              Price per night from

              $200

              Price per night from

              $200

              Distance approx 6.74 km from Chianti Show on Map

                22

                Villa Chiara

                Province of Arezzo / Pergine Valdarno

                Pergine Valdarno villa

                5 7 min stay varies

                • 5 bedrooms
                • sleeps 7
                • min stay varies
                • Nearest beach 140 mi
                • Swimming pool
                • Child Friendly

                Price per night from

                $266

                Price per night from

                $266

                Distance approx 13.32 km from Chianti

                  16

                  Farmhouse in Reggello ID 3444

                  Province of Florence / Donnini

                  Donnini farmhouse

                  1 4 min stay varies

                  • 1 bedroom
                  • sleeps 4
                  • min stay varies
                  • Swimming pool
                  • Child Friendly
                  • Air conditioning

                  Price per night from

                  $102

                  Price per night from

                  $102

                  Distance approx 8.17 km from Chianti Show on Map

                    1

                    Apt. 8

                    Province of Florence / Figline e Incisa Valdarno

                    Figline e Incisa Valdarno apartment

                    1 2 3 nights min

                    • 1 bedroom
                    • sleeps 2
                    • 3 nights min
                    • Ask about children
                    • Ask about pets

                    Price per night from

                    $144

                    Price per night from

                    $144

                    Distance approx 17.18 km from Chianti

                    (2) Excellent 

                      36

                      Villa Grassina - La Villa

                      Province of Florence / Pelago

                      Pelago house

                      3 8 min stay varies

                      • 3 bedrooms
                      • sleeps 8
                      • min stay varies
                      • Nearest beach 122 mi
                      • Swimming pool
                      • Child Friendly

                      Price per night from

                      $143

                      Price per night from

                      $143

                      Distance approx 14.14 km from Chianti

                        14

                        B & B Il Paradiso - La Cantinetta

                        Arezzo / Capolona

                        Capolona barn

                        1 2 1 night min

                        • 1 bedroom
                        • sleeps 2
                        • 1 night min
                        • Child Friendly
                        • Air conditioning
                        • Pet Friendly

                        Price per night from

                        $94

                        Price per night from

                        $94

                        Distance approx 16.46 km from Chianti

                          7

                          APARTMENT IN QUIET RESIDENTIAL AREA

                          Province of Arezzo / Arezzo

                          Arezzo apartment

                          2 6 1 night min

                          • 2 bedrooms
                          • sleeps 6
                          • 1 night min
                          • Child Friendly
                          • Private garden

                          Price per night from

                          $156

                          Price per night from

                          $156

                          Distance approx 14.02 km from Chianti

                          (5) Very Good 

                            29

                            Detached villa (1-8) with swimming pool and pizza oven.

                            Province of Siena / Castellina In Chianti

                            Castellina In Chianti villa

                            5 8 7 nights min

                            • 5 bedrooms
                            • sleeps 8
                            • 7 nights min
                            • Nearest beach 100 mi
                            • Swimming pool
                            • Child Friendly

                            Price per night from

                            $474

                            Responds fast!
                            avg. 1 hour 8 minutes

                            Price per night from

                            $474

                            Distance approx 16.56 km from Chianti

                              24

                              Chianti Big Apartment with Pool

                              Tavarnelle Val di Pesa / San Donato in Poggio

                              San Donato in Poggio apartment

                              2 4 2 nights min

                              • 2 bedrooms
                              • sleeps 4
                              • 2 nights min
                              • Beach / lakeside relaxation
                              • Swimming pool
                              • Child Friendly

                              Price per night from

                              $181

                              Price per night from

                              $181

                              Distance approx 18.43 km from Chianti

                                39

                                B&B Antico Granaione Cherry bedroom

                                Province of Siena / Rapolano Terme

                                Rapolano Terme b and b

                                1 3 min stay varies

                                • 1 bedroom
                                • sleeps 3
                                • min stay varies
                                • Child Friendly
                                • Air conditioning

                                Price per night from

                                $105

                                Price per night from

                                $105

                                Distance approx 9.55 km from Chianti

                                  5

                                  Villa Rio di Luco

                                  Reggello / Montanino

                                  Montanino villa

                                  4 8 3 nights min

                                  • 4 bedrooms
                                  • sleeps 8
                                  • 3 nights min
                                  • Swimming pool
                                  • Child Friendly
                                  • Air conditioning

                                  Price per night from

                                  $453

                                  Price per night from

                                  $453

                                  Distance approx 19.46 km from Chianti

                                    21

                                    Room Apartment A with pool near Siena

                                    Siena / Isola d'Arbia

                                    Isola d'Arbia farmhouse

                                    1 4 7 nights min

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

                                    Price per night from

                                    $266

                                    Responds fast!
                                    avg. 3 hours 34 minutes

                                    Price per night from

                                    $266

                                    Distance approx 17.39 km from Chianti

                                      6

                                      Santa Caterina Bed and Breakfast

                                      Province of Siena / Monteriggioni

                                      Monteriggioni b and b

                                      3 6 1 night min

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

                                      Price per night from

                                      $200

                                      Price per night from

                                      $200

                                      Distance approx 6.07 km from Chianti Show on Map

                                      (1) Excellent 

                                        55

                                        Chianti, Florence, Siena, Arezzo, Tuscany

                                        Province of Arezzo / Cavriglia

                                        Cavriglia villa

                                        4 8 7 nights min

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

                                        Price per night from

                                        $302

                                        Price per night from

                                        $302

                                        Distance approx 16.13 km from Chianti

                                        (2) Excellent 

                                          31

                                          Luxury Chianti Estate

                                          Greve in Chianti / Strada in Chianti

                                          Strada in Chianti cave house

                                          6 12 7 nights min

                                          • 6 bedrooms
                                          • sleeps 12
                                          • 7 nights min
                                          • Child Friendly
                                          • Air conditioning
                                          • Ask about pets

                                          Price per night from

                                          $1,473

                                          Price per night from

                                          $1,473

                                          Distance approx 5.21 km from Chianti Show on Map

                                            17

                                            Fattoria di Starda Superior Apartment Castle, Vineyard View

                                            Gaiole in Chianti / Nusenna

                                            Nusenna apartment

                                            2 5 min stay varies

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

                                            Price per night from

                                            $107

                                            Price per night from

                                            $107

                                            Distance approx 8.38 km from Chianti Show on Map

                                              13

                                              FarmHouse near CHIANTI and SIENA

                                              Bucine / Montebenichi

                                              Montebenichi apartment

                                              1 3 7 nights min

                                              • 1 bedroom
                                              • sleeps 3
                                              • 7 nights min
                                              • Nearest beach 90 mi
                                              • Swimming pool
                                              • Child Friendly

                                              Price per night from

                                              $194

                                              Price per night from

                                              $194

                                              Distance approx 18.4 km from Chianti

                                              (36) Excellent 

                                              Certificate of Excellence

                                                18

                                                Elegant 2 bedroom apt. in historic Siena residence

                                                Province of Siena / Siena

                                                Siena apartment

                                                2 5 min stay varies

                                                • 2 bedrooms
                                                • sleeps 5
                                                • min stay varies
                                                • Child Friendly
                                                • Car not necessary

                                                Certificate of Excellence

                                                Price per night from

                                                $193

                                                Responds fast!
                                                avg. 2 hours 17 minutes

                                                Price per night from

                                                $193

                                                Distance approx 17.29 km from Chianti

                                                (1) Excellent 

                                                  12

                                                  SUN APARTMENT PANORAMIC WITH SWIMMING POOL

                                                  Asciano / Crete Senesi

                                                  Crete Senesi townhouse

                                                  1 2 1 night min

                                                  • 1 bedroom
                                                  • sleeps 2
                                                  • 1 night min
                                                  • Nearest beach 60 mi
                                                  • Child Friendly
                                                  • Pet Friendly

                                                  Price per night from

                                                  $94

                                                  Price per night from

                                                  $94

                                                  Distance approx 18.77 km from Chianti

                                                  (1) Very Good 

                                                    22

                                                    Casale Aiaccia

                                                    Province of Arezzo / Arezzo

                                                    Arezzo farmhouse

                                                    3 8 3 nights min

                                                    • 3 bedrooms
                                                    • sleeps 8
                                                    • 3 nights min
                                                    • Swimming pool
                                                    • Child Friendly
                                                    • Pet Friendly

                                                    Price per night from

                                                    $340

                                                    Price per night from

                                                    $340

                                                    Distance approx 19.61 km from Chianti

                                                      23

                                                      Farm Wine Farm THE COLOMBAIO

                                                      Province of Siena / Monteriggioni

                                                      Monteriggioni farmhouse

                                                      1 24 2 nights min

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

                                                      Price per night from

                                                      $169

                                                      Price per night from

                                                      $169

                                                      Distance approx 19.73 km from Chianti

                                                        12

                                                        ALESSANDRA SEA

                                                        Province of Lucca / Massarosa

                                                        Massarosa farmhouse

                                                        2 6 min stay varies

                                                        • 2 bedrooms
                                                        • sleeps 6
                                                        • min stay varies
                                                        • Child Friendly
                                                        • Pet Friendly
                                                        • Private garden

                                                        Price per night from

                                                        $80

                                                        Price per night from

                                                        $80

                                                        Distance approx 17.35 km from Chianti

                                                        (6) Excellent 

                                                          23

                                                          Casa Castello

                                                          Province of Arezzo / Castel San Niccolo

                                                          Castel San Niccolo villa

                                                          3 6 min stay varies

                                                          • 3 bedrooms
                                                          • sleeps 6
                                                          • min stay varies
                                                          • Nearest beach 80 mi
                                                          • Suitable for children age 5+
                                                          • Ask about pets
                                                          Inquire for Rates
                                                          Inquire for Rates

                                                          Distance approx 12.2 km from Chianti

                                                            18

                                                            Molinvecchio

                                                            Talla / Vallea

                                                            Vallea villa

                                                            6 10 min stay varies

                                                            • 6 bedrooms
                                                            • sleeps 10
                                                            • min stay varies
                                                            • Nearest beach 100 mi
                                                            • Swimming pool
                                                            • Child Friendly
                                                            Inquire for Rates
                                                            Inquire for Rates

                                                            Distance approx 9.2 km from Chianti

                                                              14

                                                              Casa La Posticcia (CVC131)

                                                              Province of Arezzo / Civitella in Val di Chiana

                                                              Civitella in Val di Chiana apartment

                                                              2 4 5 nights min

                                                              • 2 bedrooms
                                                              • sleeps 4
                                                              • 5 nights min
                                                              • Child Friendly
                                                              • Pet Friendly

                                                              Price per night from

                                                              $55

                                                              Responds fast!
                                                              avg. 1 hour 22 minutes

                                                              Price per night from

                                                              $55

                                                              Distance approx 16.85 km from Chianti

                                                                28

                                                                Podere Siepi (CTC292)

                                                                Province of Siena / Castellina In Chianti

                                                                Castellina In Chianti house

                                                                2 5 7 nights min

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

                                                                Price per night from

                                                                $132

                                                                Price per night from

                                                                $132

                                                                Distance approx 16.5 km from Chianti

                                                                  10

                                                                  Villa Chiassa

                                                                  Arezzo / Chiassa Superiore

                                                                  Chiassa Superiore house

                                                                  2 6 7 nights min

                                                                  • 2 bedrooms
                                                                  • sleeps 6
                                                                  • 7 nights min
                                                                  • Swimming pool
                                                                  • Child Friendly
                                                                  • Private garden

                                                                  Price per night from

                                                                  $221

                                                                  Responds fast!
                                                                  avg. 2 hours 48 minutes

                                                                  Price per night from

                                                                  $221

                                                                  Distance approx 16.76 km from Chianti

                                                                    14

                                                                    LOFT AGRITURISMO IL CELLESE

                                                                    Province of Siena / Castellina In Chianti

                                                                    Castellina In Chianti farmhouse

                                                                    1 4 min stay varies

                                                                    • 1 bedroom
                                                                    • sleeps 4
                                                                    • min stay varies
                                                                    • Nearest beach 120 mi
                                                                    • Swimming pool
                                                                    • Child Friendly
                                                                    Inquire for Rates
                                                                    Inquire for Rates

                                                                    Distance approx 16.19 km from Chianti

                                                                      6

                                                                      Residence Cornino, Olivo 4 pax

                                                                      Province of Siena / Castellina In Chianti

                                                                      Castellina In Chianti hotel apartment

                                                                      1 4 4 nights min

                                                                      • 1 bedroom
                                                                      • sleeps 4
                                                                      • 4 nights min
                                                                      • Nearest beach 115 mi
                                                                      • Swimming pool
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $162

                                                                      Price per night from

                                                                      $162

                                                                      Distance approx 13.36 km from Chianti

                                                                        13

                                                                        The Macie (VAG114)

                                                                        Castelnuovo Berardenga / Vagliagli

                                                                        Vagliagli house

                                                                        2 4 min stay varies

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

                                                                        Price per night from

                                                                        $158

                                                                        Responds fast!
                                                                        avg. 1 hour 22 minutes

                                                                        Price per night from

                                                                        $158

                                                                        Distance approx 11.15 km from Chianti

                                                                          8

                                                                          Florentine countryside House

                                                                          Province of Florence / Reggello

                                                                          Reggello house

                                                                          2 6 min stay varies

                                                                          • 2 bedrooms
                                                                          • sleeps 6
                                                                          • min stay varies
                                                                          • Nearest beach 200 mi
                                                                          • Private garden
                                                                          Inquire for Rates
                                                                          Inquire for Rates

                                                                          Distance approx 16.83 km from Chianti

                                                                            7

                                                                            gaia House

                                                                            Province of Arezzo / Rigutino

                                                                            Rigutino condo

                                                                            2 7 min stay varies

                                                                            • 2 bedrooms
                                                                            • sleeps 7
                                                                            • min stay varies
                                                                            Inquire for Rates
                                                                            Inquire for Rates

                                                                            Distance approx 16.78 km from Chianti

                                                                              25

                                                                              oro chianti 1p

                                                                              Tavarnelle Val di Pesa / San Donato in Poggio

                                                                              San Donato in Poggio apartment

                                                                              2 4 min stay varies

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

                                                                              Price per night from

                                                                              $115

                                                                              Responds fast!
                                                                              avg. 2 hours 4 minutes

                                                                              Price per night from

                                                                              $115