Luxury rentals in Province of Grosseto

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Top-rated luxury vacation rentals in Province of Grosseto

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Luxe

The exterior of Villa Di Montesoli is highlighted by warm lighting, showcasing its rustic stone architecture. A well-kept lawn surrounds the building, along with wooden seating and garden planters, creating an inviting atmosphere in the evening light.

Villa in Buonconvento

5 out of 5 average rating, 6 reviews

Podere Maiano

Make a romantic Tuscan getaway at Villa Di Montesoli. Though the spacious nine-bedroom property offers accommodations in both a main villa and guest house, its interiors feel traditional and intimate, and amenities like a spa area, jetted tub and billiards room are hotel-worthy perks. If you can tear yourself away from the comforts of this renovated farmhouse, the surrounding Val d’Orcia landscape is worth exploring, and the city of Siena is a short drive away. Start your stay by soaking the cares away in the large pool or whirlpool spa, or sweat them out in the sauna. Take a stroll around the grounds, see what’s growing in the kitchen garden, prepare the produce on the outdoor grill and enjoy meals or a glass of wine at the al-fresco dining area. In the evening, challenge friends and family to a game of billiards or ping-pong, or relax with television or Wi-Fi access. The villa’s living spaces combine rustic architecture and formal furnishings. In one living room, stone floors and vaulted brick ceilings showcase a remodeled fireplace, traditional roll-arm sofas, carved-wood chairs and Persian-style rugs; in another, striped sofas are pulled around a large farmhouse-style fireplace. Likewise, the dining room mixes beamed ceilings and tile floors with a crystal chandelier, while red upholstered chairs provide a pop of color. The well-equipped kitchen displays country charm in wood cabinets and a cheery pottery collection. There are eight bedrooms in the main house and one bedroom in the guest house; all nine have en-suite bathrooms and either air conditioning.There are also five bedrooms with queen beds, all of which have ceiling fans. In the guest house, the bedroom has a queen bed and air conditioning. Villa Di Montesoli is about 2 miles outside the town of Buonconvento, where you’ll find restaurants, a grocery store, a church and train station. Play a match at the tennis court, 5 km away, or a round at the Borgo la Bagnaia golf course, 30 km away. Take a day trip to Siena, about 28 km away, or make the longer drive to Florence, about 95 km away. It’s 140 km to Pisa, and Rome is 230 km away. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM Main House • Bedroom 1: King size bed, En-suite bathroom with shower and bathtub, Air conditioning • Bedroom 2: King size bed, En-suite bathroom with shower, Air conditioning • Bedroom 3: King size bed, En-suite bathroom with shower and bathtub, Air conditioning, Ceiling fan • Bedroom 4: Queen size bed, En-suite bathroom, Air conditioning, Ceiling fan • Bedroom 5: Queen size bed, En-suite bathroom, Air conditioning, Ceiling fan • Bedroom 6: Queen size bed, En-suite bathroom, Air conditioning • Bedroom 7: Queen size bed, En-suite bathroom, Air conditioning, Ceiling fan • Bedroom 8: Queen size bed, En-suite bathroom, Air conditioning, Ceiling fan Guest House • Bedroom 9: Queen size bed, En-suite bathroom, Air conditioning FEATURES & AMENITIES • Alarm system • Jetted tub • Bocce Court • Vegetable garden • More under “What this place offers” below SERVICES INCLUDED • Gardener • Linen change on Saturdays • Bath linen change on Wednesday & Saturday • Products from the Organic Vegetable garden and hen eggs from the henhouse. • More under “What this place offers” below SERVICES AT EXTRA COST • Activities and excursions • Catering service • Cooking class • Wine tasting • Villa heating • Baby equipment • Event fee • Mandatory departure cleaning fee • Mandatory per day utility fee • Additional housekeeping • More under “What this place offers” below

Luxe

Villa in Radicofani

5 out of 5 average rating, 11 reviews

Villa Poggio Fibbia

Steep yourself in Tuscan history, culture and cuisine at Villa Poggio Fibbia. This beautifully renovated farmhouse is just a half-mile from the fortress at Radicofani, in a medieval village that garnered mentions in both Dante’s Divine Comedy and Boccaccio’s Decameron. Today, this vacation rental features a lovingly curated mix of traditional and modern decor and five bedrooms—the perfect Val d’Orcia escape for groups of up to ten friends or family members. Look out over the hills of Tuscany or up to the fortress tower from outdoor living areas with an infinity pool, loungers and a barbecue. During the hottest parts of the day, retreat to the shade of the al-fresco sitting and dining areas; in the evenings, relax inside by the flat-screen TVs, Wi-Fi and fireplace. Though it still has the architectural charm of the region’s traditional homes, Villa Poggio Fibbia is a modern masterpiece inside. Its beamed ceilings and stone floors are juxtaposed with sleek furnishings in the living and dining rooms, as well as playful details like orange fabric or a trompe-l’oeil wall painting. The fully equipped kitchen is equally stylish and functional, too. This luxury property has two bedrooms with king beds, a primary bedroom with a double bed, and one bedroom with two twin beds. The fifth bedroom, ideal for families on holiday with children, has a French queen bed and a twin bed. All five bedrooms have private en-suite bathrooms. Spend your stay simply enjoying the villa or exploring the area. It’s well worth the climb to the Radicofani fortress for both the views and the history, not to mention the 15-minute walk to the nearest village, where you can stop for a drink in one of the bars or sit down to a honeymoon-worthy dinner in one of the restaurants. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: Double size bed, Walk-in closet, Ensuite bathroom with stand-alone shower with chromotherapy & bathtub with hand-held shower • Bedroom 2: French Queen bed, 1 twine size bed, Ensuite bathroom with stand-alone shower with chromotherapy • Bedroom 3: King size bed, Ensuite bathroom with combo shower/bathtub, Balcony • Bedroom 4: 2 Twin size bed (can be converted into a double bed), Ensuite bathroom with stand-alone shower with chromotherapy • Bedroom 5: King size bed, Ensuite bathroom with combo shower/bathtub FEATURES & AMENITIES • Alarm system OUTDOOR FEATURES • Lounge area STAFF & SERVICES Included: • One four course dinner or one cooking class included in the price. The specific day to be agreed • Linen change - every Saturday • Light housekeeping - every Wednesday (2 hrs per day) • Towel change - every Wednesday and Saturday • Air conditioning consumption • Heating consumption At Extra Cost – advance notice may be required: •Chef and cooking classes •Van with driver for airport transfer or any other need • Activities and excursions • Additional housekeeping (40 euros/hour) (Advance notice required)

Luxe

An aerial view captures the villa surrounded by lush greenery and vineyards. The hilltop town of Montepulciano is visible in the distance, framed by rolling hills and an expansive sky featuring scattered clouds. The landscape showcases a harmonious blend of nature and historical charm.

Villa in Montepulciano

5 out of 5 average rating, 7 reviews

Villa Benefizio

Villa Benefizio offers a charming, elegant, and exclusive retreat 3 km from Montepulciano's historic center. Guests can relax or work in six stylish rooms with modern facilities and panoramic views. The villa, built around an 18th-century Renaissance guard tower, features a restored structure integrated with modern furnishings. Products from the farm are used in the Villa’s restaurants. Wi-Fi and satellite TV are available in each room.