Luxury Villa Sant’ Anna for Rent in Castiglion del Bosco, Tuscany

Villa Sant’ Anna is a five-bedroom private villa in Castiglion del Bosco, Val d’Orcia, Tuscany, accommodating 9 guests across 655 square metres. The property features five bathrooms, a 98-square-metre heated pool, and a tennis court. The entrance floor offers a living room with fireplace, indoor dining for eight, a reading/TV room, and a fully equipped kitchen with breakfast bar, alongside Room 1 with a single bed and Room 2, a king-size bedroom with walk-in closet. The first floor houses Room 3, a master bedroom with office desk, plus Rooms 4 and 5, both with ensuite bathrooms. Rates are available upon request, placing Villa Sant’ Anna among the Tuscany Villas in Val d’Orcia.

What is it Like to Stay at Villa Sant’ Anna?

Staying at Villa Sant’ Anna means settling into the Val d’Orcia countryside just 12 kilometres from Montalcino and 106 kilometres from Florence. Mornings can start with daily breakfast preparation in the entrance-floor kitchen or reading room. Afternoons move toward the heated pool, the tennis court, or a rest under the pergola-shaded lounge areas. Evenings bring meals cooked in the wood oven or on the portable BBQ, served at the outdoor dining area seating 10 guests. The five-bedroom layout, split across the entrance and first floors, gives the group a mix of ground-floor and upper-level bedrooms, each with private access to the outdoor terrace.

Which Wine Experiences are Available near Villa Sant’ Anna?

The wine experiences available near Villa Sant’ Anna are listed below.

• Brunello Wine Tasting at Castello Tricerchi, Montalcino: A guided walk through the vineyards of a medieval castle, followed by a sommelier-led tasting of three local wines, including Brunello di Montalcino and Sangiovese IGT.
• Guided Cellar Tour with Wine Tasting in Montalcino: A 90-minute visit through a historic castle estate’s cellar and vineyards, ending with a tasting of Brunello di Montalcino paired with local snacks.
• Brunello di Montalcino Tour of Two Wineries: A roughly three-hour visit to two prestigious Montalcino estates, comparing different vintages of Brunello alongside a look at the production process.
• Guided Tour of Montalcino with Winery Visit: A walking tour of the medieval hilltop town paired with a stop at a renowned local winery to taste Brunello di Montalcino.

Why Choose Villa Sant’ Anna Over Other Villas?

Choose Villa Sant’ Anna over other villas because it provides a Val d’Orcia-focused option in Castiglion del Bosco, while Villa Stabbi, Villa Agresto, and Villa Oddi offer different layouts within Kinglike Concierge’s Tuscany villa portfolio, all in the same Castiglion del Bosco estate. Villa Stabbi offers five bedrooms, suited to groups wanting a similar-sized alternative. Villa Agresto offers five bedrooms and five bathrooms, suited to groups seeking a comparable layout. Villa Oddi offers six bedrooms and a tennis court of its own, suited to slightly larger groups. Villa Sant’ Anna combines five bedrooms, a 9-guest capacity, a heated pool, and a private tennis court within a Val d’Orcia setting near Montalcino.

A comparison of Villa Sant’ Anna to other villas in Tuscany is shown in the table below.

Is Villa Sant’ Anna Suitable for Group Holidays?

Yes, Villa Sant’ Anna is suitable for group holidays through its five-bedroom layout across the entrance and first floors, accommodating up to 9 guests among shared and private spaces. The outdoor dining area, tennis court, and wood oven give the group both a central gathering spot and an active recreation option beyond the pool. Five ensuite bathrooms across the property reduce shared-facility strain during the stay. Groups seeking a comparable countryside estate can review Large Villas in Tuscany within the same portfolio.