Rent a Villa in Tuscany — Luxury Villa Rentals in Tuscany & Umbria

When you rent a villa in Tuscany the structure of the holiday changes in a way no hotel can match. Hotels work in Florence; agriturismi suit short stays; but for the trip most people actually picture, longer days, a group of friends or family in one place, lunches that stretch into the afternoon, swimming when the heat peaks, a private Tuscany villa rental is the format that delivers it. Our collection of Tuscan retreats covers the four areas of Tuscany and Umbria that most reward a week (or more) in one base: Chianti, Val d'Orcia, the Tuscan Coast and Maremma, and Umbria. The collection ranges from intimate farmhouses and holiday cottages for two through to large estate villas for family reunions of 14 or more.

Choosing the right region first

Region is the first decision and the one that has the biggest effect on what your holiday actually feels like. Chianti is the postcard, vine-covered hills between Florence and Siena, the widest villa stock, the best wine touring; busier in August. Val d'Orcia is the UNESCO landscape of cypress avenues and isolated stone farmhouses, more dramatic and quieter; further from the major cities. The Tuscan Coast and Maremma is the only part of Tuscany with proper beach access, paired with Etruscan hilltop towns and natural hot springs. Umbria, just over the eastern border, is greener, quieter, and typically 20–30% cheaper for a comparable property. Our guide to the best areas to rent a villa in Tuscany covers the trade-offs in more detail; the Tuscany map shows how the four areas sit geographically.

What to look for in a Tuscany villa

Beyond bedroom count, the details that matter on a Tuscany villa rental are typically: air conditioning in every bedroom (essential July and August, useful from late May to mid-September), pool heating (turns May, June and October from cool-pool months into swimmable ones), the condition of the access road (white gravel strada biancais standard but worth knowing if you've hired a small city car), and walking distance to a village or restaurant for guests who'd rather not drive home after dinner. For families, fully fenced pools and ground-floor bedrooms move quickly to the top of the list. For weddings or large gatherings, exclusive use and a civil-ceremony licence are usually the constraints. Our team handles those questions on every booking, see the matching family villa collection, wedding villa collection, luxury villa collection, or our private-pool villa collection.

When to book

The single biggest mistake on a Tuscany villa booking is leaving the best dates too late. The peak window, mid-July through mid-August, is reserved 9–12 months out for the strongest properties, with the largest villas (sleeping 10+) typically gone before the end of the previous season. May–June and September–October, the shoulder months that experienced Tuscany travellers usually prefer anyway, hold availability for 3–6 months, though the better-known properties go faster. For 2027, the most-asked villas are already taking holds; for 2026 shoulder dates, there is still meaningful availability. Tell us your dates and group size and we'll come back with a tailored short-list within 24 hours.

What's included with every booking

Every property in our collection has been personally visited and vetted by our team before joining the portfolio, we know the owners, the access roads, the quality of the linen, and the specific quirks of each villa. From the moment you reserve, a dedicated travel specialist handles your booking end-to-end: villa-matching, owner liaison, pre-arrival recommendations (markets, wine estates, restaurants worth a table at), and the small but important details, cots and high chairs, pre-arrival food shops, transfers, ZTL permits. The concierge service is included; there's no separate fee. If you'd prefer to start with a conversation rather than a filter, get in touch directly and we'll match a villa to your trip.