9 Best Hotels in Southern Tuscany, Tuscany

Amid rolling vineyards and olive trees, this fattoria (farmhouse) produces fine wine and olive oil and accommodates guests in apartments (sleeping up to 6) and a separate house (sleeping up to 14). The main stone house retains its enormous stone fireplace and a 16th-century family chapel next door. Lodgings have traditional wooden furniture—some antique—and full kitchens; some units have fireplaces. Half-board is available.

High above Sorano, this austere-looking 11th-century Orsini castle has spectacular views of the town and surrounding countryside. Wood-beam ceilings hang above white and pastel walls in most rooms, and windows have dark-wood shutters. A careful mix of antique and modern furniture—Rococo chairs and upholstered couches—makes for a pleasant and comfortable stay. The hotel closes for some time during the winter; the length and month of the closure vary annually.

Horseback trail rides through Tuscany's cowboy country are an integral part of the experience at this family-run country inn, where your hosts can arrange picnics, suggest itineraries, and organize weeklong tours. But nonriders don't have to mope at the bar—this agriturismo also has a pool and idyllic views. Rooms are plainly decorated with modern wooden wardrobes and desks; most are carpeted; some are enlivened by wood-beam ceilings.

Convenient to Rio Marina's charming town center and gravel beach, this comfortable hotel has pretty sea views, especially from one of the five rooms that have terraces facing the sea. Use of beach chairs and umbrellas is complimentary.

The space for part of this tiny guesthouse has been carved out of the tufa rock beneath the aqueduct at the entrance to the old town. Rooms are small and simply decorated, with painted armoires, floral print chair rails, and wood dressing tables. Only one room, the smallest, has no air-conditioning, and all are immaculately clean. A two-bedroom apartment with private terrace is available for minimum three-night stays.

The guest rooms at this 14th-century palace are named for signs of the zodiac, but the astrological reference stops at the painted symbol on the door, as each elegant room is unique—an antique sewing-machine table serves as a nightstand, a medieval-looking chandelier with a forged-iron ring and a globe hangs from a ceiling, elegant striped silk covers a wooden settee. Some rooms have ivory-color drapes hanging from baldachin beds—iron canopy beds with a painted medallion on the headpiece. A lovely garden opens behind the hotel. Five cheaper rooms, named for constellations, are available in an annex.

This ultraprivate hotel is free from noise except for the lapping of waves on the rocks; terraces and flowering gardens spill down a rocky cliff to private beaches below, and on the hill above, the owners raise purebred donkeys that you can ride over the mountain and goats that produce fresh yogurt and cheese for breakfast. Rooms feel more like those of a private home than a hotel; to complete your sense of relaxation, hydromassages and mud baths are available at the hotel's spa. You can only get here via the hotel's private boat.

In what was originally an olive oil mill, this boutique property has sweeping views of Montepulciano and Monte Amiata and rooms inspired by a traditional Tuscan aesthetic, with elements such as herringbone terra-cotta floors and patterned satin linens. The restaurant is headed by Tuscan chef and cookbook author Marco Leonelli, who prepares contemporary Italian and Mediterranean dishes using seasonal produce grown on-site or nearby. 

An elegant villa painted antique rose appears at the end of a tree-lined driveway perched on top of a hill off the main road just before Montemerano. It has expansive views and quintessential Tuscan charm. Tastefully decorated rooms—with curly ironwork or tapestries as bed headboards—are in both the main villa and a guesthouse. The farm that fans out around the villa produces fine wine and olive oil.