The Best Holiday Apartments in Tuscany

With its heated outdoor swimming pool, football fields and acres of space to explore, this countryside estate south of Pisa is the perfect solution for parents looking for a child-friendly base. Strategically positioned, it’s only a five-minute drive from the white sandy beaches of the Etruscan Coast, between Livorno and Piombino. Grown-ups can enjoy a drink by the pool as kids let off steam in the playground. Apartments sleep up to six people, with private parking and patios. An honesty-style bar and restaurant cover all the basics, and there’s also a barbecue terrace for your own al fresco meals.

Location-wise, it doesn’t get much better than this elegant 17th-century palazzo, only 10 metres (33ft) away from Florence’s cathedral. It’s so close, in fact, you can hear the bells toll from Giotto’s campanile and spy the duomo’s characteristic white, green and red marble facade. The apartments are set within a handsome Florentine home, fitted with parquet wood floors and fine Italian furniture – some even have glass skylights that glimpse the city’s ecclesiastical masterpiece. Nearby, you’ll also find the Uffizi Gallery and the Ponte Vecchio, as well as Caffè Gilli, the city’s oldest coffee house, and iconic fashion boutique LuisaViaRoma.

Yes, Florence is a must-visit, but don’t overlook Siena. This picturesque Tuscan city flaunts a well-preserved medieval centre with the Piazza del Campo, a large square where the Palio horse race is held every summer, at its heart – Bond fans will recognise it from Quantum of Solace. These renovated apartments, some with frescoed ceilings and terrazzo-tiled floors, are a short walk away from Il Campo and are a great home away from home for families and groups up to five people.

A countryside villa, surrounded by a hilly landscape covered in grapevines and cypress trees – the setting for this wine estate couldn’t be more romantic. Foodies will love the contemporary osteria that combines Tuscan traditions with culinary experiments, plus the owners also offer cooking workshops. Aspiring sommeliers can learn all about Chianti Classico’s quaffable Sangiovese-based reds in the wine cellar. From your poolside sunbed, you’ll have a great view over the valley, and the two apartments let you drink in the oh-so Italian concept of dolce far niente (the art of doing nothing).

Friend groups and families looking for the full Tuscan farmhouse experience will have a blast at this villa-topped estate, just south of Siena and 90 minutes from Florence. It boasts a host of different apartments, adorned with wood-beamed ceilings and log-burning hearths, as well as a restaurant where you can sample the region’s produce and a pool for slaking the summer heat. Go on a truffle hunt with a tartufaio (truffle seeker) and his dog, catch some fish in a nearby lake or take a bike tour through Tuscan woodlands.

Always dreamt of sleeping in a treehouse? You can make that wish come true in these stylish apartments, set amid the Tuscan trees. Eco-warriors will appreciate the accommodation’s sustainable approach. Made entirely of natural wood and insulated by cork, the apartments’ lighting and water heating systems are energy-efficient, run on renewable sources, and each one has a beautiful panoramic terrace that takes in the surrounding forest and hills.

Sleek modernity is the theme at fashionable Forte 16. This hotel is right outside of Florence’s historic centre and offers great value for money: combining the comfort of a fully equipped apartment – including your own kitchenette – with the perks of a luxury hotel. During your stay, you can make use of the wellness centre with its pools and saunas, relax on the roof terrace and pull up into free parking – useful if you’re planning to tour the Tuscan countryside. You’ll even find a free bottle of Tuscan red in your room.

Outdoorsy families and groups of friends will love these rustic stone cottages – the perfect basecamp for hikes and bike rides through the beautiful Montagnola Senese area. The family-run farmhouse, run by Daniele and Simona Amorese and their sons Davide and Alessio, also has a shared barbecue area and a panoramic swimming pool with views of the Tuscan hills. If you’d like to switch up your countryside adventure with some city-centre culture, the medieval heart of Siena is only a 30-minute drive away.

After an idyllic drive along switchback roads surrounded by chestnut trees, vineyards and olive groves, you’ll arrive at this tiny hamlet of only six houses. A Dutch couple bought this 14th-century monastery and turned it into three apartments mainly suitable for couples. The spaces flaunt original ceilings, cosy fireplaces and large, fully equipped kitchens with luxury appliances to whip up your own meals. The pool is something special: gazing across the estate’s own vineyard and Tuscany’s gnarled cypress trees, with a pergola for sipping wine while you soak up the sunset.