Tuscany, the heartland of Italian romance and rustic elegance, offers a timeless experience for those seeking a luxurious villa holiday. This enchanting region, famed for its rolling hills, vineyard-clad landscapes, and historic cities, encapsulates the essence of fine living. Holidays in Tuscany are a gateway to a world where the days are marked by panoramic sunsets, exquisite local cuisine, and the finest wines. Visitors are invited to indulge in the opulence of beautifully restored farmhouses, ancient estates, and modern retreats, each offering a unique blend of traditional charm and contemporary luxury. Whether it’s lounging beside a private pool overlooking the Tuscan countryside, exploring medieval towns, or enjoying a private wine tasting in a historic vineyard, this part of Italy promises a holiday that is as indulgent as it is unforgettable and here are our favourite villas to rent in the area.
Olivers Travels – Castello Chianti
Comprising a classical villa and tower, this eight-bedroom heritage home close to the Chianti border oozes grandeur. The mustard-coloured exterior features climbing greenery and shuttered windows. This gives way to an aristocratic interior with a ballroom, formal dining hall, dark wood antique furnishings, vaulted and timber beamed ceilings, parquet and tiled floors, a chandelier in the kitchen and oil paintings throughout. The landscaped gardens are fittingly formal, with a park, botanical gardens, a French garden, an outdoor infinity swimming pool and a BBQ terrace furnished with retro deckchairs and outdoor sofas.
Olivers Travels – Villa Martino
Book this two-storey, fully air-conditioned 19th-century farmhouse for you and up to nine guests. All five bedrooms are en-suite, one has a balcony of its own, another a balconette and two are situated on the ground floor for easy access. A built-in BBQ, outdoor kitchen, covered seating and dining areas and sizeable swimming pool, make it conducive for all generations to spend entire days in the garden, admiring the pastoral valley views. Rustic original Tuscan features bring charm to the indoor spaces, with a mix of neutral and colourful palettes that give each room its own personality.
CV Villas – Poggio Morellino
Gaze across the Elba from your classic terracotta and red-tiled villa, which is based close to Grosseto. The warm interiors provide a homely base with its rustic beamed ceilings, large arched windows, dark antique furnishings, art, ceramics, prints, paintings and drawings. The open-plan living area opens onto the terrace, where you’ll find a 14-metre pool and two pergolas enjoying open views to the far horizon. Three of the villa’s bedrooms are located on the ground floor, with the master and a single on the first. Istia d’Ombrone and Grosseto are six miles away.
CV Villas – Dimora Talamone
10 acres of land bordering the coast, provide plenty of privacy for the inhabitants of this 10-bedroom villa. They also accommodate independent areas — a sheltered walled winter garden, a rose garden and an infinity pool embedded into a lower terrace, a bar area and a gate which gives access to a beach path. Indoors, guests can relax in the sitting room and library, cook in the kitchen and eat in the dining room. In addition to seven bedrooms, there’s a huge first-floor master suite, comprising a living room, kitchenette and two super-king en-suite bedrooms.
CV Villas – Villa Torrione
This will especially suit groups requiring two distinct spaces; a quaint, beamed two-storey villa and an annexe. The larger property is designed to be the hub for socialising, with TV and billiard rooms, a bar, living and dining spaces, as well as four en-suite double bedrooms, one in a tower. Villa Torrione’s annexe has its own living, kitchen and dining spaces, with double and twin bedrooms and a shower room. Both areas share extensive grounds, a children’s playground and a spa with a wooden sauna, a bright turquoise steam bath and a jacuzzi.
The Plum Guide – Villa Monastero
Step back in time in this 16th-century convent on the edge of Sarteano, a small medieval town. Pluck some ingredients for dinner from the onsite vegetable and herb garden, which your group can later enjoy beside the huge picture window in the dining room. Decorated in neutral hues, pops of jewel tones are introduced through the textiles, bringing a richness, offset by original antique pieces. The villa has seven bedrooms for up to 14 guests, a gym and games room, a large rectangular outdoor pool surrounded by the unfolding Tuscan countryside and a pergola with daybed and lounging furniture.
The Plum Guide – The Painted Rose
Standing in contrast to the more traditional period properties you may find in the region, The Painted Rose is a contemporary villa with a sleek midcentury interior design and a slightly beach house feel. Floor-to-ceiling windows frame the open sea views, while retro furniture pieces make for a stylish aesthetic. A long, narrow infinity pool overlooks the Mediterranean, its edge seeming to blend seamlessly with the sea beyond and there are several terraces to gather for a meal or drinks. The Painted Rose is found in Monte Argentario, a short drive from Porto Santo Stefano.