Castiglion Fiorentino Rentals

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4,051 Houses

(30) Very Good 

    59

    MAS THE LEADER OF HOLIDAY HOUSE

    Province of Arezzo / Castiglion Fiorentino

    Castiglion Fiorentino villa

    4 11 7 nights min

    • 4 bedrooms
    • sleeps 11
    • 7 nights min
    • Swimming pool
    • Child Friendly
    • Pet Friendly

    Price per night from

    $387

    Price per night from

    $387

      0

      Villa Sandia D

      Province of Arezzo / Castiglion Fiorentino

      Castiglion Fiorentino house

      1 3 7 nights min

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

      Price per night from

      $98

      Responds fast!
      avg. 2 hours 8 minutes

      Price per night from

      $98

      (10) Very Good 

        48

        Tuscany Villa Bellavista

        Province of Arezzo / Castiglion Fiorentino

        Castiglion Fiorentino villa

        2 4 min stay varies

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

        Price per night from

        $155

        Price per night from

        $155

        (5) Very Good 

          47

          Villa la Foce: breathtaking panoramic view

          Province of Arezzo / Castiglion Fiorentino

          Castiglion Fiorentino villa

          4 10 7 nights min

          • 4 bedrooms
          • sleeps 10
          • 7 nights min
          • Swimming pool
          “A little paradise” We enjoyed 3 wonderful weeks in a nearly perfect surrounding.

          Price per night from

          $331

          Price per night from

          $331

            56

            Villa Magnifica

            Castiglion Fiorentino / Brolio

            Brolio villa

            9 24 min stay varies

            • 9 bedrooms
            • sleeps 24
            • min stay varies
            • Nearest beach 201 mi
            • Swimming pool
            • Child Friendly

            Price per night from

            $765

            Price per night from

            $765

            (6) Excellent 

              51

              Tuscany Villa Principe

              Province of Arezzo / Castiglion Fiorentino

              Castiglion Fiorentino villa

              5 10 min stay varies

              • 5 bedrooms
              • sleeps 10
              • min stay varies
              • Beach / lakeside relaxation
              • Swimming pool
              • Child Friendly

              Price per night from

              $322

              Price per night from

              $322

                23

                L'Arco della Lodola with Playground, Pool and WiFi

                Castiglion Fiorentino / Brolio

                Brolio house

                2 4 min stay varies

                • 2 bedrooms
                • sleeps 4
                • min stay varies
                • Nearest beach 120 mi
                • Swimming pool
                • Ask about children

                Price per night from

                $121

                Price per night from

                $121

                (4) Excellent 

                  72

                  TUSCANY VILLA PRINCIPE 8 prsns

                  Province of Arezzo / Castiglion Fiorentino

                  Castiglion Fiorentino villa

                  4 8 min stay varies

                  • 4 bedrooms
                  • sleeps 8
                  • min stay varies
                  • Swimming pool
                  • Child Friendly
                  • Ask about pets

                  Price per night from

                  $232

                  Price per night from

                  $232

                  (2) Excellent 

                    79

                    Vacation Rentals at Nightingale's Villa, Tuscany

                    Province of Arezzo / Castiglion Fiorentino

                    Castiglion Fiorentino villa

                    5 11 7 nights min

                    • 5 bedrooms
                    • sleeps 11
                    • 7 nights min
                    • Swimming pool
                    • Child Friendly
                    • Pet Friendly
                    “this could be heaven!” A well maintained, bright and inviting home for our two weeks in Tuscany. Beautiful views and amazing sunsets, a crystal blue pool and deep blue sky. In the evening, fireflies to entertain us as we sipped local wine and planne

                    Price per night from

                    $483

                    Price per night from

                    $483

                      15

                      Dreamful rooms or apartments in the heart of Tuscany

                      Province of Arezzo / Castiglion Fiorentino

                      Castiglion Fiorentino apartment

                      1 4 1 night min

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

                      Price per night from

                      $155

                      Price per night from

                      $155

                      (4) Very Good 

                        23

                        4 bedroom, Restored Farmhouse, Modern Amenities

                        Province of Arezzo / Castiglion Fiorentino

                        Castiglion Fiorentino cottage

                        4 8 7 nights min

                        • 4 bedrooms
                        • sleeps 8
                        • 7 nights min
                        • Nearest beach 24 mi
                        • Child Friendly
                        • Car not necessary
                        “Some Fantastic Views, Welcoming Hosts and a Great Place for our” Driving up through the valley from the local town of Castiglion, you realize how lucky the locals are to live in a place as rich in natural beauty as here. We spent two wonderful weeks

                        Price per night from

                        $174

                        Price per night from

                        $174

                          28

                          The Pheasant of Loyola w. three double Bedrooms

                          Castiglion Fiorentino / Brolio

                          Brolio house

                          3 6 min stay varies

                          • 3 bedrooms
                          • sleeps 6
                          • min stay varies
                          • Nearest beach 120 mi
                          • Swimming pool
                          • Ask about children

                          Price per night from

                          $156

                          Price per night from

                          $156

                            28

                            4 bedroom Villa in Sant'Angiolo, Tuscany, Italy - 5490522

                            Province of Arezzo / Castiglion Fiorentino

                            Castiglion Fiorentino villa

                            4 11 7 nights min

                            • 4 bedrooms
                            • sleeps 11
                            • 7 nights min
                            • Swimming pool
                            • Child Friendly
                            • Pet Friendly

                            Price per night from

                            $195

                            Price per night from

                            $195

                            (4) Excellent 

                              9

                              Agriturismo Le Maceie Tuscan Vacation Rental

                              Province of Arezzo / Castiglion Fiorentino

                              Castiglion Fiorentino house

                              2 6 2 nights min

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

                              Price per night from

                              $84

                              Price per night from

                              $84

                              (4) Very Good 

                                66

                                Villa Margarita, Garden Apartment with lovely Pool

                                Province of Arezzo / Castiglion Fiorentino

                                Castiglion Fiorentino villa

                                6 14 min stay varies

                                • 6 bedrooms
                                • sleeps 14
                                • min stay varies
                                • Nearest beach 23 mi
                                • Swimming pool
                                • Child Friendly

                                Price per night from

                                $717

                                Price per night from

                                $717

                                  0

                                  Villa Sandia B

                                  Province of Arezzo / Castiglion Fiorentino

                                  Castiglion Fiorentino house

                                  2 4 7 nights min

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

                                  Price per night from

                                  $174

                                  Responds fast!
                                  avg. 2 hours 8 minutes

                                  Price per night from

                                  $174

                                    34

                                    3 bedroom Villa in Fondaccio, Tuscany, Italy - 5490385

                                    Province of Arezzo / Castiglion Fiorentino

                                    Castiglion Fiorentino villa

                                    3 6 7 nights min

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

                                    Price per night from

                                    $220

                                    Price per night from

                                    $220

                                      12

                                      Big & Bright Studio in Tuscany near Cortona - WiFi

                                      Province of Arezzo / Castiglion Fiorentino

                                      Castiglion Fiorentino apartment

                                      1 3 2 nights min

                                      • 1 bedroom
                                      • sleeps 3
                                      • 2 nights min
                                      • Child Friendly

                                      Price per night from

                                      $78

                                      Price per night from

                                      $78

                                        23

                                        Podere le Spighe

                                        Province of Arezzo / Castiglion Fiorentino

                                        Castiglion Fiorentino b and b

                                        1 2 1 night min

                                        • 1 bedroom
                                        • sleeps 2
                                        • 1 night min
                                        • Swimming pool
                                        • Air conditioning

                                        Price per night from

                                        $103

                                        Price per night from

                                        $103

                                          20

                                          The Stones of Loyola with Airco, Pool and View.

                                          Castiglion Fiorentino / Brolio

                                          Brolio house

                                          1 2 min stay varies

                                          • 1 bedroom
                                          • sleeps 2
                                          • min stay varies
                                          • Nearest beach 120 mi
                                          • Swimming pool
                                          • Ask about children

                                          Price per night from

                                          $109

                                          Price per night from

                                          $109

                                            37

                                            4 bedroom Villa in Fondaccio, Tuscany, Italy - 5490381

                                            Province of Arezzo / Castiglion Fiorentino

                                            Castiglion Fiorentino villa

                                            4 10 7 nights min

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

                                            Price per night from

                                            $263

                                            Price per night from

                                            $263

                                              22

                                              3 bedroom Apartment in Sant'Angiolo, Tuscany, Italy - 5490563

                                              Province of Arezzo / Castiglion Fiorentino

                                              Castiglion Fiorentino apartment

                                              3 6 7 nights min

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

                                              Price per night from

                                              $158

                                              Price per night from

                                              $158

                                                21

                                                Villa La Pinetina

                                                Province of Arezzo / Castiglion Fiorentino

                                                Castiglion Fiorentino villa

                                                10 10 7 nights min

                                                • 10 bedrooms
                                                • sleeps 10
                                                • 7 nights min
                                                • Child Friendly
                                                • Air conditioning
                                                • Private garden

                                                Price per night from

                                                $462

                                                Price per night from

                                                $462

                                                  30

                                                  Villa Fiorentina

                                                  Province of Arezzo / Castiglion Fiorentino

                                                  Castiglion Fiorentino house

                                                  3 6 7 nights min

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

                                                  Price per night from

                                                  $222

                                                  Price per night from

                                                  $222

                                                  (1) Average 

                                                    78

                                                    Gaggioleto, magnificent panoramic villa among the singular hills of Cortona.

                                                    Province of Arezzo / Castiglion Fiorentino

                                                    Castiglion Fiorentino villa

                                                    3 6 7 nights min

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

                                                    Price per night from

                                                    $369

                                                    Price per night from

                                                    $369

                                                      0

                                                      Villa Sandia C

                                                      Province of Arezzo / Castiglion Fiorentino

                                                      Castiglion Fiorentino house

                                                      1 3 4 nights min

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

                                                      Price per night from

                                                      $98

                                                      Responds fast!
                                                      avg. 2 hours 8 minutes

                                                      Price per night from

                                                      $98

                                                        8

                                                        Holiday House Traquandi

                                                        Province of Arezzo / Castiglion Fiorentino

                                                        Castiglion Fiorentino house

                                                        1 4 1 night min

                                                        • 1 bedroom
                                                        • sleeps 4
                                                        • 1 night min
                                                        • Child Friendly
                                                        • Air conditioning
                                                        • Pet Friendly

                                                        Price per night from

                                                        $142

                                                        Price per night from

                                                        $142

                                                          17

                                                          Villa Rustica

                                                          Province of Arezzo / Castiglion Fiorentino

                                                          Castiglion Fiorentino house

                                                          9 18 7 nights min

                                                          • 9 bedrooms
                                                          • sleeps 18
                                                          • 7 nights min
                                                          • Swimming pool
                                                          • Ask about children
                                                          • Ask about pets

                                                          Price per night from

                                                          $342

                                                          Price per night from

                                                          $342

                                                          (1) Very Good 

                                                            53

                                                            Villa del Colle ideal location for family reunion

                                                            Province of Arezzo / Castiglion Fiorentino

                                                            Castiglion Fiorentino villa

                                                            7 16 7 nights min

                                                            • 7 bedrooms
                                                            • sleeps 16
                                                            • 7 nights min
                                                            • Swimming pool

                                                            Price per night from

                                                            $349

                                                            Price per night from

                                                            $349

                                                              10

                                                              Large Studio apartment in Historical Centre - WiFi

                                                              Province of Arezzo / Castiglion Fiorentino

                                                              Castiglion Fiorentino apartment

                                                              1 3 2 nights min

                                                              • 1 bedroom
                                                              • sleeps 3
                                                              • 2 nights min
                                                              • Child Friendly

                                                              Price per night from

                                                              $92

                                                              Price per night from

                                                              $92

                                                                31

                                                                Villa Angelisa D

                                                                Province of Arezzo / Castiglion Fiorentino

                                                                Castiglion Fiorentino apartment

                                                                2 7 7 nights min

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

                                                                Price per night from

                                                                $127

                                                                Responds fast!
                                                                avg. 2 hours 8 minutes

                                                                Price per night from

                                                                $127

                                                                  30

                                                                  9 bedroom Villa in Potassa, Tuscany, Italy - 5747562

                                                                  Castiglion Fiorentino / Brolio

                                                                  Brolio villa

                                                                  9 18 7 nights min

                                                                  • 9 bedrooms
                                                                  • sleeps 18
                                                                  • 7 nights min
                                                                  • Swimming pool
                                                                  • Child Friendly
                                                                  • Air conditioning

                                                                  Price per night from

                                                                  $928

                                                                  Price per night from

                                                                  $928

                                                                    37

                                                                    8 bedroom Villa in Piegaio, Tuscany, Italy - 5490391

                                                                    Province of Arezzo / Castiglion Fiorentino

                                                                    Castiglion Fiorentino villa

                                                                    8 15 7 nights min

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

                                                                    Price per night from

                                                                    $199

                                                                    Price per night from

                                                                    $199

                                                                      20

                                                                      Villa Valdichiana Villa in Tuscany, Arezzo villa, holiday in Italian villa,

                                                                      Province of Arezzo / Castiglion Fiorentino

                                                                      Castiglion Fiorentino house

                                                                      9 18 7 nights min

                                                                      • 9 bedrooms
                                                                      • sleeps 18
                                                                      • 7 nights min
                                                                      • Ask about children
                                                                      • Air conditioning
                                                                      • Pet Friendly

                                                                      Price per night from

                                                                      $975

                                                                      Price per night from

                                                                      $975

                                                                        22

                                                                        4 bedroom Villa in Castroncello, Tuscany, Italy - 5669459

                                                                        Castiglion Fiorentino / Castroncello

                                                                        Castroncello villa

                                                                        4 8 7 nights min

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

                                                                        Price per night from

                                                                        $472

                                                                        Price per night from

                                                                        $472

                                                                          39

                                                                          4 bedroom Villa in Patalecchia, Tuscany, Italy - 5490602

                                                                          Province of Arezzo / Castiglion Fiorentino

                                                                          Castiglion Fiorentino villa

                                                                          5 10 7 nights min

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

                                                                          Price per night from

                                                                          $226

                                                                          Price per night from

                                                                          $226

                                                                            74

                                                                            9 bedroom Villa in Fattoria Montecchio, Tuscany, Italy - 5765171

                                                                            Castiglion Fiorentino / Castroncello

                                                                            Castroncello villa

                                                                            9 18 7 nights min

                                                                            • 9 bedrooms
                                                                            • sleeps 18
                                                                            • 7 nights min
                                                                            • Swimming pool
                                                                            • Child Friendly
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $835

                                                                            Price per night from

                                                                            $835

                                                                              28

                                                                              Villa Angelisa B

                                                                              Province of Arezzo / Castiglion Fiorentino

                                                                              Castiglion Fiorentino apartment

                                                                              2 4 7 nights min

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

                                                                              Price per night from

                                                                              $101

                                                                              Responds fast!
                                                                              avg. 2 hours 8 minutes

                                                                              Price per night from

                                                                              $101

                                                                              About Castiglion Fiorentino

                                                                              Millions of people come to visit Tuscany every year, but a stay in the quiet village of Castiglion Fiorentino, where beautiful countryside and mountains surround you everywhere you turn, is a great way to get the Tuscan experience without enduring throngs of visitors. You'll find most of the top restaurants in town and trendy boutique shopping along Via Nazionale, the main street in Castiglion Fiorentino. Several stunning old buildings can also be found on the street known as Via Vecchie Ciminiere.

                                                                              Here are some of the other must-see attractions and activities in the area:

                                                                              • Castello di Fiorentina: This nearby village is surrounded by great architecture and offers picturesque views of the countryside.
                                                                              • Try the Cuisine: The food in this part of Tuscany is simple, yet full of flavor. Try the Panzanella, a delicate ravioli made in a rich truffle sauce.
                                                                              • Apennine Mountains: These mountains offer walking and hiking trails that take you past the olive trees that the area is famous for.
                                                                              • Church of Saint Angelo: The most popular church in Castiglion Fiorentino dates back to the 12th century and is one of the many ancient structures in the middle of the historical center.
                                                                              • Play Golf: Several golf courses for all levels of players have sprung up in recent years throughout the area. Casentino Golf Club is the most popular amongst the locals.

                                                                              It doesn't matter when you decide to Castiglion Fiorentino because the Fiera Antiquaria is one of the many events that take place year-round. Held on the first Sunday of every month, people from all over Italy come to look at clothing and locally made food and crafts from over 500 vendors. Some of the other major events in the area include the horse race in June known as the Palio dei Rioni and Giostra del Sacarino an equestrian competition in nearby Arezzo that has been held every June for over 400 years.

                                                                              The Tuscan region is one of the most popular vacation spots in the world, which means that there is no shortage of vacation rentals available year-round. Book a condo that overlooks the vineyards and beautiful countryside, or rent a property downtown near the restaurants and shopping.

                                                                              A vacation to Castiglion Fiorentino wouldn't be complete without visiting some of the nearby cities and towns that make this area so popular. If you have some extra time to explore, plan a day trip to the world-renowned art on display in the town of Arezzo or the canals and historical attractions of Florence, both which can be reached within 30 minutes by car.