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Hand-picked Holiday Homes & Villas in the Province of Siena – An Authentic Holiday Experience in the Heart of Tuscany

Located in south-eastern Tuscany, the Province of Siena is one of Italy’s best-known and most scenically diverse regions. Those looking for holiday homes in the Province of Siena will discover rolling hills, vineyards, olive groves and the distinctive clay landscapes of the Crete Senesi, which are among the most iconic features of the Sienese countryside. The province is also home to the UNESCO World Heritage Site of the Val d'Orcia, one of Tuscany's most celebrated landscapes and an ideal destination for an authentic holiday in the heart of Tuscany.

In addition to the provincial capital of Siena, towns such as San Gimignano, Pienza, Montepulciano, Montalcino and Monteriggioni are among the region’s cultural highlights. Equally distinctive are the Crete Senesi south of Siena—an almost surreal landscape of rolling clay hills surrounding Asciano. The Chianti Classico wine region and parts of the Val di Chiana further enhance the province’s remarkable diversity. Our carefully selected collection includes beautiful villas with pools as well as charming holiday apartments on wine estates. 

Whether surrounded by unspoilt countryside or close to historic towns, our hand-picked holiday accommodation in the Province of Siena offers the perfect setting to experience Tuscany's rich cultural heritage, renowned wine regions and authentic way of life.

Tips & Activities in the Province of Siena

Visit the Historic Centre of Siena

Siena's historic centre, a UNESCO World Heritage Site, is one of Europe's most impressive medieval city centres. Piazza del Campo, Siena Cathedral and the city's narrow streets create an exceptionally harmonious historic setting. Our hand-picked holiday accommodation near Siena provides the perfect base for experiencing the city's rich history, remarkable architecture and unique atmosphere.

Historic Sites and Cultural Highlights

Among the province's most celebrated destinations are San Gimignano with its medieval towers, Pienza, renowned as the ideal Renaissance town, and Montepulciano, whose historic architecture and spectacular hilltop setting overlooking the Val di Chiana make it one of Tuscany's most captivating places to visit. Montalcino is known for its imposing fortress and beautifully preserved historic centre. Colle di Val d'Elsa, famous for its long tradition of crystal glass production, and Monteriggioni, encircled by its remarkably well-preserved medieval walls, are also among the region's cultural highlights.

Nature and Outdoor Activities

The Province of Siena offers excellent opportunities for hiking, cycling and leisurely excursions through some of Tuscany's most celebrated scenery. Particularly striking are the rolling hills of the Val d'Orcia and the distinctive landscapes of the Crete Senesi, with their characteristic clay hills, calanchi and sweeping panoramic views. The town of Asciano is an excellent starting point for exploring this unique landscape. The vineyards of the Chianti Classico wine region and parts of the Val di Chiana provide further opportunities for scenic walks and cycling tours.

Spiritual Sites and Abbeys

Among the province's most remarkable religious landmarks are the Romanesque Abbey of Sant'Antimo set in a peaceful valley near Montalcino, and the Abbey of San Galgano, renowned for its striking roofless church. Nearby, the Chapel of Montesiepi houses the legendary Sword in the Stone. According to tradition, the knight Galgano Guidotti thrust his sword into the rock as a symbol of his renunciation of warfare and it can still be seen there today.

Gourmet Delights, Wine and Regional Specialities

The cuisine of the Province of Siena is deeply rooted in Tuscany's rural traditions. Typical specialities include rustic dishes based on bread, legumes and locally sourced meat, as well as handmade pasta such as Pici and a variety of game dishes. The province is internationally renowned for its outstanding wines: Chianti Classico, Vino Nobile di Montepulciano and Brunello di Montalcino are among Italy's most prestigious wines and have helped shape the region's outstanding culinary reputation.

Wellness and Spa Towns

The Province of Siena is home to some of Tuscany’s most renowned spa towns and has a long tradition of thermal bathing. Destinations such as Bagno Vignoni, Chianciano Terme, Rapolano Terme and San Casciano dei Bagni have attracted visitors seeking relaxation and wellbeing since Roman times. Our hand-picked holiday homes and villas in the Province of Siena offer the perfect setting for combining a relaxing stay with the region’s celebrated thermal heritage.

While the historic spa towns of Bagno Vignoni, Chianciano Terme, Rapolano Terme and San Casciano dei Bagni are renowned for their thermal traditions, Bagni San Filippo offers one of Tuscany's most extraordinary natural spa experiences. Located on the edge of the Val d'Orcia near Castiglione d'Orcia, its warm sulphur-rich waters flow through a wooded valley, creating spectacular limestone formations and natural pools along the Fosso Bianco. A visit offers a unique opportunity to experience Tuscany's thermal landscape in an unspoilt natural setting.

Traditions and Events

The cultural life of the Province of Siena is deeply rooted in centuries-old customs and historic celebrations. The most famous of these is the Palio di Siena, the traditional horse race held in Piazza del Campo every year on 2 July and 16 August. More than a spectacular event, it lies at the heart of the city's identity and has been celebrated for centuries. Those who rent a holiday home in the Province of Siena during this time have the unique opportunity to experience the vibrant atmosphere of the Contrade and witness one of Italy's most remarkable cultural events. 

Discover our hand-picked selection of holiday homes in the Province of Siena.
Carlotta Carrai from Idea Toscana will be happy to advise you personally and help you find the perfect place to stay in Tuscany.

80 Holiday Homes in the province of Siena

    • Ferienhaus Podere Casello - Pool
    • Ferienhaus mit Pool-Podere Casello-Außenansicht
    • Ferienhaus mit Pool-Podere Casello-Außenansicht
    • Ferienhaus mit Pool-Podere Casello-Außenansicht
      Ferienhaus "Podere Casello" mit 4 Schlafzimmern und Pool, Holiday House in the province of Siena
      8
      4
      3
      from €1,750
      per week
      • Ferienhaus Villa Renata - Terrasse
      • Ferienhaus Villa Renata - Außenansicht
      • Ferienhaus Villa Renata - Pool
      • Ferienhaus Villa Renata - Terrasse
        Villa Renata mit 3 Schlafzimmern und Privatpool, Holiday House in the province of Siena
        7
        3
        2
        2
        on request
        • Ferienwohnung Il Pino - Garten mit Pergola
        • Ferienwohnung Il Pino - Wohnzimmer
        • Ferienwohnung Il Pino - Küche
        • Ferienwohnung Il Pino - Küche
          Ferienwohnung "Il Pino" - auf Landgut mit Pool, Holiday Apartment in the province of Siena
          6
          3
          1
          1
          from €1,200
          per week
          • Luftbild - Borgo Santinovo
          • Luftbild - Borgo Santinovo
          • Luftbild - Borgo Santinovo
          • Außenansicht - Borgo Santinovo
            Borgo Santinovo - Weingut mit Pool im Chianti, Wine estate with 12 Units in the province of Siena
            • Weingut Agriturismo Cesani - mit Pool - herrlicher Lage
            • Weingut Agriturismo Cesani - Imbiss am Pool
            • Weingut Agriturismo Cesani - wunderschöner Ausblick
            • Weingut Agriturismo Cesani - Zimmer Iris
              Agriturismo Cesani - Weingut bei San Gimignano, Wine estate with 11 Units in the province of Siena
              4
                POGGETTO, Villa in the province of Siena
                10
                5
                3
                from €150
                per night
                  ARANCIO, Holiday Apartment in the province of Siena
                  4
                  2
                  1
                  from €97
                  per night
                    LA PERGOLA, Villa in the province of Siena
                    8
                    5
                    3
                    from €138
                    per night
                      MANDARINO, Holiday Apartment in the province of Siena
                      2
                      1
                      1
                      from €78
                      per night
                        VERZURE, Holiday House in the province of Siena
                        3
                        2
                        1
                        from €70
                        per night
                          SAN LORENZO 3, Holiday Apartment in the province of Siena
                          4
                          2
                          1
                          from €107
                          per night
                            BIBBIANELLO, Villa in the province of Siena
                            10
                            5
                            6
                            from €429
                            per night
                              CASINA NEL BOSCO, Holiday House in the province of Siena
                              4
                              2
                              2
                              from €170
                              per night
                                SAN LORENZO 7, Holiday Apartment in the province of Siena
                                4
                                2
                                1
                                from €107
                                per night
                                  SAN LORENZO 9, Holiday Apartment in the province of Siena
                                  4
                                  1
                                  1
                                  from €74
                                  per night
                                    SAN LORENZO13, Holiday Apartment in the province of Siena
                                    4
                                    2
                                    2
                                    from €74
                                    per night
                                      Aquila, Holiday Apartment in the province of Siena
                                      5
                                      3
                                      2
                                      on request
                                        SAN LORENZO 1, Holiday Apartment in the province of Siena
                                        2
                                        1
                                        1
                                        from €72
                                        per night
                                          CASENOVOLE, Villa in the province of Siena
                                          10
                                          5
                                          6
                                          from €620
                                          per night
                                            AURORA, Villa in the province of Siena
                                            6
                                            2
                                            2
                                            from €207
                                            per night
                                              Villa Montepescini, Villa in the province of Siena
                                              14
                                              7
                                              5
                                              from €750
                                              per night
                                              • Ferienhaus Podere Casello - Pool
                                              • Ferienhaus mit Pool-Podere Casello-Außenansicht
                                              • Ferienhaus mit Pool-Podere Casello-Außenansicht
                                              • Ferienhaus mit Pool-Podere Casello-Außenansicht
                                                39
                                                LU-1-20

                                                Ferienhaus "Podere Casello" mit 4 Schlafzimmern und Pool, Holiday House in the province of Siena

                                                Ferienhaus mit Privatpool im Herzen der Toskana
                                                • Max. 8 Guests
                                                • 160 m2 living space
                                                • 4 Bedrooms
                                                • 3 Bathroom
                                                WLAN · Washing machine · Dishwasher · Pool · child-friendly
                                                from €1,750
                                                per week
                                                • Ferienhaus Villa Renata - Terrasse
                                                • Ferienhaus Villa Renata - Außenansicht
                                                • Ferienhaus Villa Renata - Pool
                                                • Ferienhaus Villa Renata - Terrasse
                                                  26
                                                  LU-3-20

                                                  Villa Renata mit 3 Schlafzimmern und Privatpool, Holiday House in the province of Siena

                                                  • Max. 7 Guests
                                                  • 130 m2 living space
                                                  • 3 Bedrooms
                                                  • 2 Bathroom
                                                  • 2 pets allowed
                                                  WLAN · Washing machine · Dishwasher · Jacuzzi · Pool · child-friendly · pet friendly
                                                  on request
                                                  • Ferienwohnung Il Pino - Garten mit Pergola
                                                  • Ferienwohnung Il Pino - Wohnzimmer
                                                  • Ferienwohnung Il Pino - Küche
                                                  • Ferienwohnung Il Pino - Küche
                                                    31
                                                    534

                                                    Ferienwohnung "Il Pino" - auf Landgut mit Pool, Holiday Apartment in the province of Siena

                                                    • Max. 6 Guests
                                                    • 110 m2 living space
                                                    • 3 Bedrooms
                                                    • 1 Bathroom
                                                    • 1 pet allowed
                                                    WLAN · Washing machine · TV · Shared pool · child-friendly · pet friendly
                                                    from €1,200
                                                    per week from 5 pers. €35
                                                    • Luftbild - Borgo Santinovo
                                                    • Luftbild - Borgo Santinovo
                                                    • Luftbild - Borgo Santinovo
                                                    • Außenansicht - Borgo Santinovo
                                                      93
                                                      IT-1139

                                                      Borgo Santinovo - Weingut mit Pool im Chianti, Wine estate with 12 Units in the province of Siena

                                                      WLAN · Pool · child-friendly · pet friendly
                                                      • Weingut Agriturismo Cesani - mit Pool - herrlicher Lage
                                                      • Weingut Agriturismo Cesani - Imbiss am Pool
                                                      • Weingut Agriturismo Cesani - wunderschöner Ausblick
                                                      • Weingut Agriturismo Cesani - Zimmer Iris
                                                        38
                                                        IT-1080

                                                        Agriturismo Cesani - Weingut bei San Gimignano, Wine estate with 11 Units in the province of Siena

                                                        • Max. 4 Guests
                                                        • 135 m2 living space
                                                        WLAN · Air condition · Breakfast · Pool · Organic wine estate
                                                          39
                                                          051001

                                                          POGGETTO, Villa in the province of Siena

                                                          Das Haus hat 10 Schlafplätze. Im Ergeschoß gibt es einen großes Wohnzimmer mit Kamin, eine Küche, ein Doppelzimmer, ein Zimmer mit 2 Einzelbetten und ein Bad mit Dusche. Im ersten Stock befinden sich 2 Doppelzimmer, ein Zimmer mit 2 Betten, ein Bad mit...
                                                          • Max. 10 Guests
                                                          • 144 m2 living space
                                                          • 5 Bedrooms
                                                          • 3 Bathroom
                                                          Air condition · Washing machine · TV · Dishwasher · Pool · pet friendly
                                                          from €150
                                                          per night
                                                            25
                                                            002001

                                                            ARANCIO, Holiday Apartment in the province of Siena

                                                            Wohnung Arancio- 4 Betten - 55 qm - besteht aus einem Wohnzimmer mit Küchenzeile (Backofen, Herd, Kühlschrank mit Gefrierfach und Waschmaschine), einem Schlafzimmer mit Doppelbett, einem Schlafzimmer mit zwei Einzelbetten und einem Bad mit Dusche.
                                                            • Max. 4 Guests
                                                            • 55 m2 living space
                                                            • 2 Bedrooms
                                                            • 1 Bathroom
                                                            Air condition · Washing machine · Shared pool · pet friendly
                                                            from €97
                                                            per night
                                                              39
                                                              0225

                                                              LA PERGOLA, Villa in the province of Siena

                                                              Unabhängiges Haus für 8 Personen mit privatem Garten und Pool in einem typisch toskanischen Dorf.
                                                              • Max. 8 Guests
                                                              • 160 m2 living space
                                                              • 5 Bedrooms
                                                              • 3 Bathroom
                                                              Washing machine · TV · Dishwasher · Pool · pet friendly
                                                              from €138
                                                              per night
                                                                23
                                                                002002

                                                                MANDARINO, Holiday Apartment in the province of Siena

                                                                Apartment Mandarino - Studio 2 Betten - 39 qm - besteht aus einem Wohnzimmer mit Küchenzeile (Backofen, Herd, Kühlschrank mit Gefrierfach und Waschmaschine), einem Doppelbett und einem Bad mit Dusche. Beide Wohnungen sind mit einer unabhängigen Heizung...
                                                                • Max. 2 Guests
                                                                • 39 m2 living space
                                                                • 1 Bedrooms
                                                                • 1 Bathroom
                                                                Air condition · Washing machine · Shared pool · pet friendly
                                                                from €78
                                                                per night
                                                                  27
                                                                  074501

                                                                  VERZURE, Holiday House in the province of Siena

                                                                  37 km. westlich von Siena entfernt liegt dieses kleine Landhaus, das erst kürzlich renoviert wurde und von einem großen (750 qm.) Garten umgeben ist.
                                                                  • Max. 3 Guests
                                                                  • 55 m2 living space
                                                                  • 2 Bedrooms
                                                                  • 1 Bathroom
                                                                  pet friendly
                                                                  from €70
                                                                  per night
                                                                    32
                                                                    061503

                                                                    SAN LORENZO 3, Holiday Apartment in the province of Siena

                                                                    Appartment nr. 3 (70 qm) – im Erdgeschoß, für 4 Personen, Wohnzimmer mit Küchenzeile (Herd, Kühlschrank und Ofen) , 2 Doppelzimmer und Bad mit behindertengerechter Dusche. Verbindungstür zum App. 7
                                                                    • Max. 4 Guests
                                                                    • 70 m2 living space
                                                                    • 2 Bedrooms
                                                                    • 1 Bathroom
                                                                    TV · Dishwasher · Shared pool · pet friendly
                                                                    from €107
                                                                    per night
                                                                      39
                                                                      003701

                                                                      BIBBIANELLO, Villa in the province of Siena

                                                                      Villa 10 Betten mit privatem Pool.
                                                                      • Max. 10 Guests
                                                                      • 350 m2 living space
                                                                      • 5 Bedrooms
                                                                      • 6 Bathroom
                                                                      Air condition · Washing machine · TV · Dishwasher · Pool · pet friendly
                                                                      from €429
                                                                      per night
                                                                        32
                                                                        079203

                                                                        CASINA NEL BOSCO, Holiday House in the province of Siena

                                                                        Ein gemütliches Landhaus in einer sehr privaten, abgeschiedenen Lage.
                                                                        • Max. 4 Guests
                                                                        • 60 m2 living space
                                                                        • 2 Bedrooms
                                                                        • 2 Bathroom
                                                                        Air condition · TV · Shared pool · Pool · pet friendly
                                                                        from €170
                                                                        per night
                                                                          35
                                                                          061507

                                                                          SAN LORENZO 7, Holiday Apartment in the province of Siena

                                                                          Appartment nr. 7 (70 qm) – für 4 Personen, Wohnzimmer mit Küchenzeile (Herd, Kühlschrank und Ofen) , ein Doppelzimmer und Bad mit behindertengerechter Dusche. Verbindungstür zum App. 3
                                                                          • Max. 4 Guests
                                                                          • 70 m2 living space
                                                                          • 2 Bedrooms
                                                                          • 1 Bathroom
                                                                          TV · Shared pool · pet friendly
                                                                          from €107
                                                                          per night
                                                                            30
                                                                            061509

                                                                            SAN LORENZO 9, Holiday Apartment in the province of Siena

                                                                            Appartment nr. 9 (50 qm) – im Erdgeschoß, für 2 Personen, Wohnzimmer mit Küchenzeile (Herd, Kühlschrank und Ofen) und Schlafcouch für 2 Personen, ein Doppelzimmer und Bad mit Dusche.
                                                                            • Max. 4 Guests
                                                                            • 50 m2 living space
                                                                            • 1 Bedrooms
                                                                            • 1 Bathroom
                                                                            TV · Dishwasher · Shared pool · pet friendly
                                                                            from €74
                                                                            per night
                                                                              34
                                                                              061513

                                                                              SAN LORENZO13, Holiday Apartment in the province of Siena

                                                                              Appartment n. 13 (48 qm) im Erdgeschoß, für 2 Personen, Wohnzimmer mit Küchenzeile (Herd, Kühlschrank und Ofen) , ein Doppelzimmer und Bad mit Dusche, Verbindungstür zum App. 12
                                                                              • Max. 4 Guests
                                                                              • 48 m2 living space
                                                                              • 2 Bedrooms
                                                                              • 2 Bathroom
                                                                              TV · Dishwasher · Shared pool · pet friendly
                                                                              from €74
                                                                              per night
                                                                                18
                                                                                007001

                                                                                Aquila, Holiday Apartment in the province of Siena

                                                                                APT AQUILA – 5 Schlafplätze – 91 m². Erdgeschoss.
                                                                                • Max. 5 Guests
                                                                                • 91 m2 living space
                                                                                • 3 Bedrooms
                                                                                • 2 Bathroom
                                                                                Air condition · Washing machine · TV · Dishwasher · pet friendly
                                                                                on request
                                                                                  34
                                                                                  061501

                                                                                  SAN LORENZO 1, Holiday Apartment in the province of Siena

                                                                                  Appartment nr. 1 (40 qm) - im 1. Stock, für 2 Personen, Wohnzimmer mit Küchenzeile (Herd, Kühlschrank und Ofen) ,. Doppelzimmer mit Bad und Dusche. Im Wohnzimmer gibt es eine Verbindungstür zum App. nr. 6
                                                                                  • Max. 2 Guests
                                                                                  • 40 m2 living space
                                                                                  • 1 Bedrooms
                                                                                  • 1 Bathroom
                                                                                  TV · Shared pool · pet friendly
                                                                                  from €72
                                                                                  per night
                                                                                    49
                                                                                    013701

                                                                                    CASENOVOLE, Villa in the province of Siena

                                                                                    Eingebettet ins Grün der toskanischen Landschaft, schöne freistehende Villa für 10 Personen mit Garten, beheiztem Pool, Whirlpool und Sauna.
                                                                                    • Max. 10 Guests
                                                                                    • 340 m2 living space
                                                                                    • 5 Bedrooms
                                                                                    • 6 Bathroom
                                                                                    Air condition · Washing machine · TV · Dishwasher · Shared pool · Pool · pet friendly
                                                                                    from €620
                                                                                    per night
                                                                                      35
                                                                                      001001

                                                                                      AURORA, Villa in the province of Siena

                                                                                      Casa Aurora wurde in zwei Wohnungen aufgeteilt, die jeweils über einen separaten Eingang verfügen. Beide Apartments sind hübsch und rustikal eingerichtet, was eine sehr freundliche und familiäre Atmosphäre schafft. Die Wohnungen werden ausschließlich...
                                                                                      • Max. 6 Guests
                                                                                      • 80 m2 living space
                                                                                      • 2 Bedrooms
                                                                                      • 2 Bathroom
                                                                                      Air condition · Washing machine · TV · Dishwasher · Pool · pet friendly
                                                                                      from €207
                                                                                      per night
                                                                                        47
                                                                                        079202

                                                                                        Villa Montepescini, Villa in the province of Siena

                                                                                        Umgeben von Grün und Natur, eine neu restaurierte Villa und ein Nebengebäude, ideal für eine Gruppe bis zu 14 Personen. Dem Gast stehen ein Rasengarten und ein Swimmingpool zur Verfügung
                                                                                        • Max. 14 Guests
                                                                                        • 200 m2 living space
                                                                                        • 7 Bedrooms
                                                                                        • 5 Bathroom
                                                                                        Air condition · Washing machine · TV · Dishwasher · pet friendly
                                                                                        from €750
                                                                                        per night