Best Private Pool Villas in Tuscany (2026)

Castelfalfi is a medieval hamlet resort in the hills between Florence, Pisa and Siena, built around a restored 12th-century village. Most of its 146 rooms and suites share the resort's pools, but a handful of standalone villas – led by Casale I Bianchi – come with a private heated pool and veranda set apart from the main buildings.

Casale I Bianchi has five bedrooms across two floors, each with its own bathroom, making it better suited to a family or group booking than a couple's escape. The resort's smaller Village Villas also carry private plunge pools at a lower price point, for travelers who want privacy without the full five-bedroom villa.

Beyond the villas, Castelfalfi functions as a full countryside resort: an 18-hole golf course, a wellness spa, and five restaurants and bars spread across the estate. It sits roughly equidistant from Florence and Pisa airports, making it one of the easier private-pool properties in Tuscany to reach.

Rosewood Castiglion del Bosco is a 5,000-acre estate in Val d'Orcia founded by the Ferragamo family, built around a restored medieval hamlet in the Brunello di Montalcino wine region. Eleven villas, converted from 17th- and 18th-century farmhouses, are scattered across the property – and every one of them has its own private heated infinity pool, not a pool shared between villas.

Each villa comes with a Land Rover Defender or similar 4x4 for guests to explore the estate, which includes its own winery and Italy's only private golf club reserved for guests. Villa sizes and layouts vary, from smaller one-bedroom units to multi-bedroom villas suited to a family group, but the pool is always private to that single villa.

This is the flagship Val d'Orcia address for genuinely private villa pools – Siena is 25 miles away, and Florence is roughly a 2-hour drive. May–June and September are the best months to visit, before the summer heat and after the harvest crowds thin out.

Borgo Santo Pietro is a 13th-century manor house outside Chiusdino, set within 5 hectares of walled gardens roughly 40 minutes from Siena. Most of its rooms and suites share the property's main pool, but the La Casa dei Fiori Bianchi Pool House is a separate two-suite building where each suite has its own 36 sqm saltwater pool, complete with a jacuzzi and cascade for hydrotherapy.

The two suites can be connected internally through the garden to form a single complex for a family or two-couple booking, or booked separately for full privacy. The setting is intimate rather than resort-scale – Borgo Santo Pietro has one of the smallest guest counts of any hotel on this list, which keeps the walled gardens and pool houses quiet.

The estate grows its own produce for the kitchen and runs an on-site apothecary and spa. This is the pick for a honeymoon or anniversary stay where seclusion matters more than resort facilities.

L'Andana Tenuta La Badiola is a former Grand Duke's summer residence in the Maremma, the coastal region of southern Tuscany, roughly 10 minutes from Castiglione della Pescaia and the Tyrrhenian coast. The Il Granaio Suites, opened in a renovated historic barn on the estate, each come with a private pool overlooking the vineyards – a different setting from the hilltop Val d'Orcia and Chianti properties on this list.

For a larger group, La Scuderia is a standalone 4-bedroom villa on the 2,000-acre estate with its own private pool and garden, bookable as a full residence. The estate produces its own wine and olive oil, and the on-site restaurant is run under Michelin-starred chef Enrico Bartolini.

This is the only property on this list within easy reach of the Tuscan coast rather than inland hill country – useful for travelers who want a private pool by day and a beach nearby.

Castello di Velona is a hilltop castle resort overlooking Val d'Orcia, built around its own thermal spring and winery. The Suite with Panoramic Terrace and Private Pool sits in the castle's Ancient South Tower: an 80 sqm suite opening onto a private 180 sqm terrace with a gazebo, stone dining table and a pool filled with the property's own natural hot spring water rather than a standard chlorinated pool.

The terrace looks directly over the Brunello di Montalcino vineyards and the wider Val d'Orcia valley – one of the more distinctive views among Tuscany's private pool properties. The estate's shared thermal pools and spa are open to all guests, but this tower suite is the only accommodation category with a pool reserved for a single suite.

Montalcino is roughly 45 minutes from Siena, putting Castello di Velona close to both Rosewood Castiglion del Bosco and the Brunello wine estates that define the area.