Villa rentals near San Gimignano
San Gimignano is so perfect; it can seem like a medieval stage set (it’s real, we promise). As a movie backdrop it has been a favourite of Franco Zeffirelli, among many other directors. Parts of “Tea with Mussolini” we’re filmed here. Guarded by a ring of fortified walls, Tuscany’s “Medieval Manhattan” is a hill-town of stone towers, rustic medieval palaces and narrow, winding lanes.
Our San Gimignano villas are scattered amid some of Tuscany’s prettiest countryside — the hills around San Gimignano. They include luxury converted stone farmhouses, distinguished villas ideal for a large gathering, and smaller properties just right for a family vacation in Tuscany. All these villas near San Gimignano have air-conditioned bedrooms — which you’ll appreciate in the hot Tuscan summer. Many have air-conditioning throughout.
Every Tuscany Now & More villa has a private swimming pool, free use of our concierge service, for pre-trip arrangements and an emergency number available 24/7 while you are in-destination. Your concierge can arrange a private chef, daily maid service, or shopping delivered to your villa, and memorable experiences like Tuscan cookery classes in your holiday rental’s kitchen.
We can arrange unforgettable experiences from your San Gimignano villa, like a Tuscan cookery class in your holiday rental kitchen or a guided cycle ride through the San Gimignano vineyards that ends up at a famous gelateria in the town square. (Why not both?)
At Tuscany Now & More we take pride in our service. For 30 years we have been matching every guest to their ideal villa in Italy. Someone from our small team visits or stays in every San Gimignano villa we list. We know the area intimately. This is why we keep our portfolio small — and probably why the world’s leading luxury travel magazine says we’re Tuscany’s best villa company.
To also read what real travellers think of our service, and the experience of staying in a Tuscany Now & More luxury villa, check out our verified reviews.
About San Gimignano
Twenty-five miles north-west of Siena, this is one of Italy’s most spectacular small towns, set amid the photogenic scenery of the central Tuscan hills. San Gimignano is famed for its standing medieval towers, the painted interior of its medieval Collegiate Church, and a fine white wine made from grapes picked on the surrounding hills: Vernaccia di San Gimignano.
An immaculately preserved Gothic centre is a magnet for visitors, certainly, but in its backstreets and frescoed churches, you can easily find a corner to yourself.
Staying nearby in a San Gimignano villa gives you the chance to see San Gimignano at its best: early in the morning and at dusk. Without the day-trippers, the place takes on an entirely different atmosphere: secretive, silent, even a little spooky. Standing alone, in Piazza della Cisterna, the town suddenly feels every one of its 800 or so years of age.
What to Do in San Gimignano
Twin central squares — Piazza della Cisterna and Piazza del Duomo — are the heart of the town.
Dominating the latter is the Collegiata (a Collegiate Church, basically a cathedral without a bishop’s seat). Its interior walls are covered in fresco, a technique used in medieval times to apply fresh paint to wet plaster.
The earliest artworks here date to medieval Tuscany. They recount narratives from the Old and New Testaments, including a lurid “Last Judgement” by Sienese painter Taddeo di Bartolo above the main door. It’s like a scene from “The Walking Dead”.
Also inside, the Chapel of Santa Fina is a Renaissance collaboration between sculptor Benedetto di Maiano and architect Giuliano da Maiano (both from Fiesole) and Florentine Renaissance painter, Domenico Ghirlandaio.
Ghirlandaio’s frescoes tell the legend of San Gimignano’s local saint, Fina. As she lies dying, flowers bloom spontaneously from a plank (her makeshift bed). On the left-hand wall, angels hover, ringing tower bells in her memory. A few San Gim sights and shops shut each March 12th, to remember their little 13th-century saint.
Nearby, the painting collection at the Museo Civico testifies to the artists who passed through San Gimignano in its heyday. The showcase is a “Maestà” (Virgin Mary surrounded by saints) painted in 1317 by Lippo Memmi.
After you have seen the art, you can climb the 54m (177-ft.) medieval Torre Grossa. Views stretch for miles over hills smothered in vines and olive groves.
Moving way along the historical timeline, San Gimignano has a growing reputation for contemporary art. The Galleria Continua is a warren-like space that often displays works by global names like Antony Gormley and Ai Weiwei
There are several excellent rural walks around San Gimignano, through the vines and olive groves that approach the town on all sides, or among the wildflowers in spring and early summer.
For more on what to see and do in San Gimignano, see our San Gimignano travel guide.
Food and Drink in San Gimignano
The longest queue in San Gimignano is not for a famous sight or museum, but for the sweet-toothed kitchen artisans at Gelateria Dondoli. This ice-cream parlour is more often known as Gelateria “di Piazza” after its location on San Gim’s prettiest square, Piazza della Cisterna.
Ice-cream flavours range from traditional to weird-and-wonderful, like “Rosemary’s Baby” (raspberry and rosemary), blackberries and lavender, or zabaione con vin santo (custard with the famous Tuscan sweet wine, Vin Santo).
Their signature flavour is crema di Santa Fina, a cream gelato with added saffron. The town has long been a centre for organic saffron farming.
San Gimignano is also the name behind Tuscany’s only dry white DOCG wine, Vernaccia di San Gimignano. This straw-coloured white dates at least to the 1200s.
Inside San Gimignano’s ruined 14th-century castle, the Vernaccia di San Gimignano Wine Experience offers tastings and displays on the wine’s history.
Almost 2,000 acres of terrain around San Gimignano are given over to olive trees. Fruits are farmed in late autumn and pressed to produce a renowned extra-virgin olive oil.
