Country estate for 4 people in the hills of Chianti.1/16Between cypresses and cycads
Tuscany | Whether a restored farm house or agriturismo – during a country vacation in Tuscany you can experience the nature and regional cuisine.
Per week from USD 466show 480 offers
You will find several holiday apartments on this 300-hectare estate in Gaiole.2/16Holiday on a wine-growing estate
Chianti in autumn | The grape harvest in the heart of Tuscany starts in mid-September. Lively celebrations accompany this time, which you can genuinely experience with a holiday home on the wine-growing estate.
Per week from USD 490show 129 offers
“Very attractive stylish furnishings,” wrote one customer about the holiday home in Tuscany.3/16The best in Tuscany
Tuscany | Would you like to know which holiday home or apartment is particularly worth spending a holiday in? Here we'll show you the accommodation in Tuscany, which has received the best reviews from our customers.
Per week from USD 299show 265 offers
Secluded country house for up to 12 people in Chianti.
5/16Holiday with your own pool
Tuscany | Give your Italian holiday the perfect touch with a holiday home plus pool! And let yourself completely relax with a view of the rolling hills and vineyards.
Per week from USD 598show 2,809 offers
You’ll find this exceptional holiday apartment for four people in the heart of Rome.6/16That certain something
Italy | In the end it comes down to the furnishings if one feels comfortable. That applies to both your home and holiday. These holiday houses have a particularly fancy interior which gives them a unique flair for your vacation.
Per week from USD 578show 95 offers
Apartment situated in an old palazzo near St Peter’s Basilica.7/16Trip to the Eternal City
Rome | After you have visited the antique sights and exciting museums you can return to your retreat and remain completely independent.
Per week from USD 1,005show 2 offers
Luxurious country estate for up to 20 people in Umbria.8/16Everyone can come along here!
Italy | Circles of friends, large families, teams, and other groups of travellers can experience exciting and relaxing holidays in these XXL houses for 20 people and more.
Per week from USD 1,866show 139 offers
Experience quintessential Italy with a holiday home in Chianti
From a romantic holiday apartment on the cobbled streets of a medieval village, to a rustic rural holiday home surrounded by green meadows and centuries-old farmhouses, there are holiday rentals to suit every taste in beautiful Chianti. This region of Tuscany, between Florence and Siena, is quintessentially Italian: lush rolling hills, dotted with vineyards, interrupted by picturesque stone villages that perch impossibly on hilltops. Above all, it is known for its traditional wineries, producing some of the world's best-loved red wines.
World-class wine and tasty tours
Wine tasting in Chianti is simple to organise and rewarding. Countless vineyards offering informative tastings are crammed into this comparatively small region, making it feasible to visit several in just one day from a holiday house based anywhere in Chianti. Rent a car and set out from your holiday apartment with absolute freedom to explore secluded farmhouses and out-of-the-way cellars throughout Barberino Val d'Elsa, unearthing exquisite wines and superb food, including Chianti's prized olives. Chianti's wine is hard to stop sipping, so those visitors that would prefer not to drive can take part in all-inclusive tours covering multiple wineries and leisurely lunches. Many of the region's vineyards are accessible by public transport from your holiday rental, including Castelo Vicchiomaggio, a winery surrounding an impressive medieval castle.
Holiday houses in hilltop towns: beautiful landscapes meet rich culture
Book a holiday rental in Chianti - in the heart of Italy - and feel history around every corner. Romantic old towns dot the landscape: Montefioralle, a few miles from Greve in Chianti, still has its fortified walls to keep out invading armies, while Giaole in Chianti is a rustic town with gorgeous old buildings and winding alleys - an idyllic visual counterpart to the rolling, sun-drenched hills that fade into the distance. For families with kids, the region also offers endless hiking and biking trails. Rent a holiday home in a romantic Tuscan town or a holiday house in the countryside, and Chianti's superb landscapes, wine and heritage will take care of the rest.