The Best Luxury Villas in Tuscany

Just 10mi (16km) outside of Florence, nestled among a 494-acre (200ha) expanse of tangled vineyards and silver-hued olive groves, is a soaring hilltop castle. Dating back to the 11th century, the artfully restored property now has six sophisticated guest rooms as well as an outdoor pool, an Italian garden and an ancient cellar. Have your private chef design a custom menu celebrating local, sun-blushed ingredients, before ending the night with a glass of Chianti wine. You can either rent a single room or the entire castle for an extra-special event.

This is the stuff of fairytales: a small, stone-built cottage dating back to the year 1200, surrounded by a thick green forest that creeps all the way up to the door. The enchanting cottage can sleep up to six people and is ideal for families or small groups of friends. In the summer months, cool off by jumping in the outdoor pool or set off on a hike and take refuge under the dense canopy of the nearby forest. The quiet luxury of this property is best paired with a hearty Italian meal, so bike to the nearest village, Catiglion Fiorentino, and stock up on Tuscan delicacies that you can then enjoy al fresco in the garden’s gazebo.

This comfortable villa sleeps up to 12 people and is known for its added, modern luxuries in an old-school setting. Make the most out of the outdoor pool and take time to relax on the shaded patio, before setting out into the small medieval town of Pietrasanta. You can spend time exploring the area’s artistic heritage – Michelangelo once visited Pietrasanta to learn about carving marble from local artisans – or bike down to the Marina di Pietrasanta and take a dip in the Tyrrhenian Sea.

This remarkable six-bedroom Tuscan farmhouse, in the heart of the Chianti wine region, quietly presides over the flickering skyline of San Gimignano. Combining classical Tuscan style with modern touches – think terracotta floors and open wooden beams, plus a restaurant-standard kitchen, a pool and a playground for children – this villa reaches the heights of the luxury Italian lifestyle. Spend your days lounging by the pool or relaxing in the garden, internal courtyard or one of the multiple spacious terraces. A personalised concierge service is also available to ensure you have the best possible stay.

If a remote setting is what you’re after, this six-bedroom villa will deliver. Located near the medieval village of Santa Fiora, and a 25mi (40km) car ride away from the coastline, this tranquil property is the perfect place to recharge and enjoy pared-back, rural life. Spend your days relaxing by the pool or challenging your friends to a tennis game, and when you feel like exploring, nearby Santa Fiora has been voted one of the most beautiful villages in Italy more than once.

There’s more to Tuscany than wine – the region is equally famous for its olive oil production. Experience this firsthand with a stay in this restored 200-year-old olive mill, on a sprawling estate. The six-bedroom villa retains many of its original features and artfully integrates them with modern touches, such as a Nespresso machine and a Smeg fridge. Laze by the pool and gaze out over enchanting olive groves and dark green cypress tree silhouettes. Or better yet, set out to learn more about the area by joining an olive oil tasting.

If sweeping, unobstructed views make you feel like you can finally breathe, this luxuriously appointed farmhouse is the place to book. The Tuscan-style building retains its original style and adds in modern amenities, such as a small inside gym and a seasonal outdoor pool. With eight bedrooms, there’s plenty of room for both friends and family. Enjoy a dip in the pool, fire up the barbecue and savour the view as you eat a rustic Italian meal on the rooftop terrace.