Montegrossi Rentals

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5,141 Houses

Great rentals within 20 miles that match your search

Distance approx 14.27 km from Montegrossi

(5) Excellent 

    44

    Villa Caprera, Siena Farmhouse. Suite Il Tinaio

    Province of Siena / Siena

    Siena villa

    1 4 5 nights min

    • 1 bedroom
    • sleeps 4
    • 5 nights min
    • Child Friendly
    • Pet Friendly

    Price per night from

    $135

    Price per night from

    $135

    Distance approx 15.76 km from Montegrossi

    (1) Excellent 

      19

      Villa with pool close to Florence Country house il Faeto

      Rignano sull'Arno / San Donato in Collina

      San Donato in Collina b and b

      5 9 7 nights min

      • 5 bedrooms
      • sleeps 9
      • 7 nights min
      • Nearest beach 100 mi
      • Swimming pool
      • Child Friendly

      Price per night from

      $615

      Price per night from

      $615

      Distance approx 4.14 km from Montegrossi

      (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

        Price per night from

        $347

        Price per night from

        $347

        Distance approx 16.98 km from Montegrossi

        (20) Excellent 

          114

          Restored Tuscan farmhouse with pool and views

          Province of Florence / Certaldo

          Certaldo house

          4 9 4 nights min

          • 4 bedrooms
          • sleeps 9
          • 4 nights min
          • Nearest beach 88 mi
          • Swimming pool
          • Child Friendly
          “Under theTuscan Sun” There are no words to describe the beauty here. When we drove up to the house, we thought there was a mistake. Surely this beautifully restored "Under the Tuscan Sun" farmhouse with majestic views of rolling hillside towns dotted

          Price per night from

          $257

          Price per night from

          $257

          Distance approx 7.17 km from Montegrossi

          (1) Very Good 

            22

            Villa Lena - Green Valley of Chianti

            Greve in Chianti / Lucolena

            Lucolena villa

            5 9 7 nights min

            • 5 bedrooms
            • sleeps 9
            • 7 nights min
            • Swimming pool
            • Ask about children
            • Pet Friendly

            Price per night from

            $244

            Price per night from

            $244

            Distance approx 16.99 km from Montegrossi

            (4) Excellent 

              25

              Converted Barn Vacation Rental in Tuscany

              Province of Florence / Certaldo

              Certaldo cottage

              2 4 4 nights min

              • 2 bedrooms
              • sleeps 4
              • 4 nights min
              • Swimming pool
              • Child Friendly
              • Air conditioning
              “We had a very relaxing stay in a beautiful setting.” The house is newly renovated and very clean. The setting is spectacular with beautiful views. It is in a great location for easy access to popular tourist attractions. However, we did have to provid

              Price per night from

              $120

              Price per night from

              $120

              Distance approx 8.54 km from Montegrossi

                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

                Distance approx 12.43 km from Montegrossi

                (2)  

                  47

                  The Poacher

                  Greve in Chianti / San Polo in Chianti

                  San Polo in Chianti villa

                  3 5 min stay varies

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

                  Price per night from

                  $174

                  Price per night from

                  $174

                  Distance approx 12.71 km from Montegrossi

                    20

                    Villa with view in Tuscany close to Florence

                    Province of Florence / Reggello

                    Reggello b and b

                    2 4 3 nights min

                    • 2 bedrooms
                    • sleeps 4
                    • 3 nights min
                    • Swimming pool
                    • Ask about children

                    Price per night from

                    $77

                    Price per night from

                    $77

                    Distance approx 8.52 km from Montegrossi

                    (3) Excellent 

                      41

                      Classic house in the heart of Tuscany Chianti area

                      Province of Florence / Greve in Chianti

                      Greve in Chianti house

                      3 6 3 nights min

                      • 3 bedrooms
                      • sleeps 6
                      • 3 nights min
                      • Nearest beach 145 mi
                      • Child Friendly
                      • Air conditioning

                      Price per night from

                      $103

                      Responds fast!
                      avg. 2 hours 36 minutes

                      Price per night from

                      $103

                      Distance approx 17.53 km from Montegrossi

                        29

                        Tuscany with View and Heart

                        Province of Arezzo / Monte San Savino

                        Monte San Savino apartment

                        1 4 min stay varies

                        • 1 bedroom
                        • sleeps 4
                        • min stay varies
                        • Nearest beach 120 mi
                        • Swimming pool
                        • Ask about children

                        Price per night from

                        $107

                        Price per night from

                        $107

                        Distance approx 11.57 km from Montegrossi

                        (1) Excellent 

                          30

                          Apartment Joshua - Farmhouse Molinuzzo - Florence

                          Province of Florence / Barberino Val d'Elsa

                          Barberino Val d'Elsa apartment

                          2 4 2 nights min

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

                          Price per night from

                          $250

                          Price per night from

                          $250

                          Distance approx 16.85 km from Montegrossi

                            28

                            Gorgeous independent house, in Chianti, with pool

                            Province of Florence / San Casciano in Val di Pesa

                            San Casciano in Val di Pesa house

                            3 6 7 nights min

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

                            Price per night from

                            $208

                            Price per night from

                            $208

                            Distance approx 6.74 km from Montegrossi

                            (12) Excellent 

                              42

                              Charming Villa in Lamole- Greve in Chianti ideal for family and friends reunions

                              Province of Florence / Greve in Chianti

                              Greve in Chianti villa

                              9 15 7 nights min

                              • 9 bedrooms
                              • sleeps 15
                              • 7 nights min
                              • Nearest beach 143 mi
                              • Swimming pool
                              • Child Friendly
                              “A perfect tuscan holiday home!” A comfortable, family-style place in a beautiful setting, with all the amenities. Beautiful grounds and pool. Perfectly located near charming towns, wineries, restaurants, markets in the chianti region. Close to Siena

                              Price per night from

                              $288

                              Price per night from

                              $288

                              Distance approx 14.1 km from Montegrossi

                              (7) Excellent 

                                22

                                Casa vacanze Bellavista

                                Province of Florence / San Casciano in Val di Pesa

                                San Casciano in Val di Pesa farmhouse

                                1 4 3 nights min

                                • 1 bedroom
                                • sleeps 4
                                • 3 nights min
                                • Child Friendly
                                • Pet Friendly

                                Price per night from

                                $82

                                Price per night from

                                $82

                                Distance approx 13.57 km from Montegrossi

                                (8) Excellent 

                                  40

                                  Monterzi 4

                                  Province of Siena / Siena

                                  Siena villa

                                  2 4 7 nights min

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

                                  Price per night from

                                  $141

                                  Price per night from

                                  $141

                                  Distance approx 14.21 km from Montegrossi

                                  (2) Very Good 

                                    17

                                    Holidays in Tuscany - Apartment near Florence

                                    Province of Florence / Florence

                                    Florence apartment

                                    2 4 7 nights min

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

                                    Price per night from

                                    $91

                                    Price per night from

                                    $91

                                    Distance approx 16.14 km from Montegrossi

                                    (6) Excellent 

                                      50

                                      Farmhouse in the Chianti Classico area, App. 2+1g

                                      Greve in Chianti / Strada in Chianti

                                      Strada in Chianti farmhouse

                                      1 3 min stay varies

                                      • 1 bedroom
                                      • sleeps 3
                                      • min stay varies
                                      • Beach / lakeside relaxation
                                      • Swimming pool
                                      • Child Friendly

                                      Price per night from

                                      $109

                                      Price per night from

                                      $109

                                      Distance approx 14.42 km from Montegrossi

                                        26

                                        Monteriggioni Suite 4

                                        Province of Siena / Monteriggioni

                                        Monteriggioni house

                                        2 4 7 nights min

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

                                        Price per night from

                                        $138

                                        Price per night from

                                        $138

                                        Distance approx 12.61 km from Montegrossi

                                          27

                                          The Cellar

                                          Greve in Chianti / San Polo in Chianti

                                          San Polo in Chianti house

                                          3 5 min stay varies

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

                                          Price per night from

                                          $174

                                          Price per night from

                                          $174

                                          Distance approx 16.14 km from Montegrossi

                                          (8) Excellent 

                                            45

                                            Contryhouse 9 kms to Florence with pool 4+2

                                            Greve in Chianti / Strada in Chianti

                                            Strada in Chianti farmhouse

                                            2 6 min stay varies

                                            • 2 bedrooms
                                            • sleeps 6
                                            • min stay varies
                                            • Swimming pool
                                            • Child Friendly
                                            • Air conditioning

                                            Price per night from

                                            $154

                                            Price per night from

                                            $154

                                            Distance approx 15.51 km from Montegrossi

                                              11

                                              Tuscany Two-Bedroom Flat in Medieval Hill top Hamlet Panoramic Views

                                              Tuscany / Province of Florence

                                              Province of Florence house

                                              1 4 1 night min

                                              • 1 bedroom
                                              • sleeps 4
                                              • 1 night min
                                              • Suitable for children age 5+
                                              • Air conditioning

                                              Price per night from

                                              $169

                                              Price per night from

                                              $169

                                              Distance approx 17.27 km from Montegrossi

                                              (10) Excellent 

                                                12

                                                3 bedrooms with garden in the heart of Chianti

                                                Province of Florence / Montespertoli

                                                Montespertoli house

                                                3 7 min stay varies

                                                • 3 bedrooms
                                                • sleeps 7
                                                • min stay varies
                                                • Nearest beach 78 mi
                                                • Child Friendly
                                                • Private garden

                                                Price per night from

                                                $129

                                                Responds fast!
                                                avg. 1 hour 5 minutes

                                                Price per night from

                                                $129

                                                Distance approx 8.54 km from Montegrossi

                                                  23

                                                  Bright and spacious home in the heart of Tuscany.

                                                  Province of Florence / Figline e Incisa Valdarno

                                                  Figline e Incisa Valdarno house

                                                  4 7 3 nights min

                                                  • 4 bedrooms
                                                  • sleeps 7
                                                  • 3 nights min
                                                  • Child Friendly

                                                  Price per night from

                                                  $129

                                                  Price per night from

                                                  $129

                                                  Distance approx 11.17 km from Montegrossi

                                                  (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

                                                    $193

                                                    Price per night from

                                                    $193

                                                    Distance approx 14.23 km from Montegrossi

                                                      23

                                                      5 bedroom Villa in Rota, Tuscany, Italy - 5584116

                                                      Reggello / Ruota

                                                      Ruota villa

                                                      5 9 7 nights min

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

                                                      Price per night from

                                                      $554

                                                      Price per night from

                                                      $554

                                                      Distance approx 8.52 km from Montegrossi

                                                      (76) Excellent 

                                                        69

                                                        Poggerina luxury private villa with stunning view

                                                        Province of Florence / Greve in Chianti

                                                        Greve in Chianti villa

                                                        4 8 min stay varies

                                                        • 4 bedrooms
                                                        • sleeps 8
                                                        • min stay varies
                                                        • Swimming pool
                                                        • Child Friendly
                                                        • Air conditioning
                                                        “A beautiful villa in an amazing place, wonderful nice owner.” We stayed in the Villa late September 2014. The weather was nice, but not warm enough for the pool. We had amazing bio garden tomatoes every day, and loved the beautiful garden and house.

                                                        Price per night from

                                                        $280

                                                        Responds fast!
                                                        avg. 3 hours 10 minutes

                                                        Price per night from

                                                        $280

                                                        Distance approx 17.43 km from Montegrossi

                                                        (2) Excellent 

                                                          21

                                                          Tuscan Country house in the chianti area with pool

                                                          Province of Florence / San Casciano in Val di Pesa

                                                          San Casciano in Val di Pesa house

                                                          6 12 min stay varies

                                                          • 6 bedrooms
                                                          • sleeps 12
                                                          • min stay varies
                                                          • Child Friendly
                                                          • Pet Friendly

                                                          Price per night from

                                                          $398

                                                          Price per night from

                                                          $398

                                                          Distance approx 7.24 km from Montegrossi

                                                            28

                                                            3 bedroom Villa in Panzano, Tuscany, Italy - 5228823

                                                            Province of Arezzo / Bucine

                                                            Bucine villa

                                                            3 6 7 nights min

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

                                                            Price per night from

                                                            $284

                                                            Price per night from

                                                            $284

                                                            Distance approx 14.23 km from Montegrossi

                                                              25

                                                              7 bedroom Villa in Rota, Tuscany, Italy - 5584117

                                                              Reggello / Ruota

                                                              Ruota villa

                                                              5 16 7 nights min

                                                              • 5 bedrooms
                                                              • sleeps 16
                                                              • 7 nights min
                                                              • Swimming pool
                                                              • Child Friendly
                                                              • Ask about pets

                                                              Price per night from

                                                              $680

                                                              Price per night from

                                                              $680

                                                              Distance approx 15.79 km from Montegrossi

                                                              (1) Excellent 

                                                                40

                                                                Casale Bonizio

                                                                Barberino Val d'Elsa / Vico D'elsa

                                                                Vico D'elsa house

                                                                4 12 min stay varies

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

                                                                Price per night from

                                                                $194

                                                                Price per night from

                                                                $194

                                                                Distance approx 13.9 km from Montegrossi

                                                                  41

                                                                  Stronghold

                                                                  Province of Florence / Barberino Val d'Elsa

                                                                  Barberino Val d'Elsa apartment

                                                                  2 4 min stay varies

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

                                                                  Price per night from

                                                                  $127

                                                                  Price per night from

                                                                  $127

                                                                  Distance approx 12.82 km from Montegrossi

                                                                    48

                                                                    Village Gebbia

                                                                    Province of Arezzo / Civitella in Val di Chiana

                                                                    Civitella in Val di Chiana house

                                                                    5 10 min stay varies

                                                                    • 5 bedrooms
                                                                    • sleeps 10
                                                                    • min stay varies
                                                                    • Swimming pool
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $261

                                                                    Price per night from

                                                                    $261

                                                                    Distance approx 18.09 km from Montegrossi

                                                                      22

                                                                      Impruneta

                                                                      Province of Florence / Impruneta

                                                                      Impruneta villa

                                                                      5 10 7 nights min

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

                                                                      Price per night from

                                                                      $1,186

                                                                      Responds fast!
                                                                      avg. 48 minutes

                                                                      Price per night from

                                                                      $1,186

                                                                      Distance approx 17.03 km from Montegrossi

                                                                      (3) Excellent 

                                                                        16

                                                                        romantic ancient tuscan villa B&B near Firenze

                                                                        Province of Florence / Barberino Val d'Elsa

                                                                        Barberino Val d'Elsa villa

                                                                        7 14 4 nights min

                                                                        • 7 bedrooms
                                                                        • sleeps 14
                                                                        • 4 nights min
                                                                        • Nearest beach 97 mi
                                                                        • Swimming pool
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $1,026

                                                                        Price per night from

                                                                        $1,026

                                                                        Distance approx 14.15 km from Montegrossi

                                                                        (1) Excellent 

                                                                          24

                                                                          House il Santo Chianti , Tuscany, Florence, Italy

                                                                          Province of Florence / Barberino Val d'Elsa

                                                                          Barberino Val d'Elsa house

                                                                          5 10 min stay varies

                                                                          • 5 bedrooms
                                                                          • sleeps 10
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Pet Friendly

                                                                          Price per night from

                                                                          $294

                                                                          Price per night from

                                                                          $294

                                                                          Distance approx 13.57 km from Montegrossi

                                                                            21

                                                                            One Bedroom Villa at Castello di Montalto in Chianti

                                                                            Province of Siena / Siena

                                                                            Siena villa

                                                                            1 2 3 nights min

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

                                                                            Price per night from

                                                                            $141

                                                                            Price per night from

                                                                            $141

                                                                            Distance approx 3.38 km from Montegrossi

                                                                            (16) Excellent 

                                                                              40

                                                                              Chianti Cashmere Vacation Rentals, Rural Tuscany

                                                                              Province of Siena / Radda in Chianti

                                                                              Radda in Chianti house

                                                                              3 6 7 nights min

                                                                              • 3 bedrooms
                                                                              • sleeps 6
                                                                              • 7 nights min
                                                                              • Nearest beach 80 mi
                                                                              • Swimming pool
                                                                              • Child Friendly

                                                                              Price per night from

                                                                              $257

                                                                              Price per night from

                                                                              $257