Luxury rentals in Province of Grosseto

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Top-rated luxury vacation rentals in Province of Grosseto

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Luxe

Villa

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

Mulino della Solaia

Muliono dello Solaia is a gorgeous Tuscan villa situated near the village of Iesa, south of Siena. Originally an olive oil mill, the structure has been restored and renovated into a fabulous vacation home, balancing exquisite contemporary comforts with vintage rustic artistry. Superb amenities include a swimming pool, alfresco dining and barbeque, and a gourmet kitchen. Five lovely bedroom suites with ensuite bathrooms accommodate families, destination wedding guests, and groups of friends up to ten in size. The historic home maintains much of its original character, with beautiful stone walls and facades, brick-lined thresholds, terracotta tile, and expertly landscaped gardens. The lower terrace features an ample swimming pool with elegant lounge chairs overlooking panoramic valley views. A covered patio extending from the house features a lovely outdoor sofa and dining table. Lush lawns surrounding the house offer a welcoming venue for special ceremonies or playful afternoons. Wide glass doors join the interior loggia to the terrace, forming an alfresco veranda in the summer months and a luminous, hearth-warmed habitat in winter. This space includes a comfortable lounge area with fireplace and sound system, flowing through a brick archway into a dining room furnished with timeless Tuscan elegance. The villa's kitchen features chef-grade appliances, a central table, and arched French doors to the patio. A small media room with table is located next to an antique millstone. The bedrooms balance fresh modern comforts with a dreamy, bucolic charm. There are three rooms with king beds, one with a queen, and one with a pair of twin beds. Each enjoys lovely views and light, and one of the king rooms opens directly to the garden. Air conditioning throughout the villa keeps you comfortable in the summer months. This secluded location in the Sienese hills gives a profound taste of the region's rich natural beauty and unique culture. There is a local food/convenience store about ten minutes away, and you're an easy drive from the Renaissance treasures of Siena. You're also an easy daytrip from the Grosetto region along the Tyrrhenian coast. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1: King size bed, Ensuite bathroom with stand-alone shower, Air conditioning • Bedroom 2: Queen size bed, Ensuite bathroom with stand-alone bathtub, Air conditioning • Bedroom 3: Twin size bed (can be converted to queen), Ensuite bathroom with stand-alone shower, Air conditioning • Bedroom 4: King size bed, Ensuite bathroom with stand-alone shower, Air conditioning • Bedroom 5: King size bed, Ensuite bathroom with stand-alone shower, Air conditioning, Direct access to garden FEATURES & AMENITIES • More under “What this place offers” below OUTDOOR FEATURES • More under “What this place offers” below STAFF & SERVICES Included • Daily housekeeping (maximum 3 hours) • Change of linen and towels once a week • Concierge services • Complimentary welcome basket • Complimentary welcome dinner - Only for stays of 7 nights • More under “What this place offers” below Extra cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

Luxe

Villa

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

A spacious outdoor area is featured, showcasing a covered terrace with seating arrangements. Elegant curtains frame the openings to the interiors, while landscaped green grass extends towards the property. Soft lighting enhances the cozy environment as dusk sets in, highlighting the architectural details.

Villa

Villa Sofia

Gravel roads wind through hills to this Tuscan estate, and olive groves and vineyards drop into the sea in the views from its gardens. High ceilings echo the landscape’s expanse indoors, and rooms showcase works by female artists. Covered terraces extend the living areas outdoors and around the pool. Drive to gardens with tarot-inspired sculptures just outside the nearby medieval town of Capalbio. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone rain shower & bathtub, Bidet, Walk-in closet, Television, Safe, Desk, Terrace • Bedroom 2: King size bed, Ensuite bathroom with shower/bathtub combo, Bidet, Desk, Terrace • Bedroom 3: King size bed, Ensuite bathroom with 2 stand-alone rain showers, Bidet, Terrace • Bedroom 4: 2 Twin size beds (can be converted to double), Ensuite bathroom with shower/bathtub combo • Bedroom 5: 2 Twin size beds, Ensuite bathroom with bathtub, Bidet, Desk OUTDOOR FEATURES • Outdoor sound system • Outdoor living space • Fire pit • Garden • More under “What this place offers” below STAFF & SERVICES Included: • Gardener • Pool maintenance • Laundry service (excluding dry cleaning) • More under “Add-on services” below Extra Cost (advance notice may be required): • Activities and excursions • Masseuse • Babysitting service

Luxe

The outdoor area features a private swimming pool surrounded by wooden decking and sun loungers. Towering cypress trees are visible, along with a cozy gazebo. The farmhouse blends rustic architecture with modern amenities, set against a clear blue sky.

Villa

Beautiful modern villa with pool in Val D'Orcia

Nestled into the rolling hillside of Tuscany, this luxurious farmhouse enjoys sweeping views decorated with emerald lawns, lush gardens, and mature trees. With 17 beds, this spacious estate is perfect for large gatherings. Spend your days shooting pool, swimming, and playing tennis on the grass court. Inside, gorgeous architecture and high-end finishings await. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary:Double size bed, Ensuite bathroom with stand-alone shower • Bedroom 2: Double size bed, Ensuite bathroom with stand-alone shower & bathtub • Bedroom 3: Double size bed, Ensuite bathroom with stand-alone shower & bathtub • Bedroom 4: Double size bed, Ensuite bathroom with stand-alone shower & bathtub • Bedroom 5: 2 Twin size beds (can be converted to a double bed ) Ensuite bathroom with stand-alone shower • Bedroom 6: 2 Twin size beds (can be converted to a double bed , Ensuite bathroom with stand-alone shower • Bedroom 7: Double size bed, Ensuite bathroom with stand-alone shower • Bedroom 8: Double size bed, Ensuite bathroom with stand-alone shower • Bedroom 9: Double size bed, Ensuite bathroom with stand-alone shower FEATURES & AMENITIES • Home theater STAFF & SERVICES Extra Cost (advance notice may be required): • Activities and excursions

Luxe

The villa is set in a lush green landscape, featuring a spacious infinity pool surrounded by sun loungers. The building’s rustic architecture complements the natural surroundings, with expansive lawns and trees framing the view of the distant hills.

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Il Poderone - Luxury Villa con piscina privata

Villa con piscina riscaldata, finemente ristrutturata situata in una tenuta privata di 700 ettari. Affittandola potrai vivere un'esperienza immersiva nei ritmi e nell'atmosfera suggestiva della maremma. Cureremo la tua permanenza in ogni dettaglio grazie al servizio di pulizia giornaliero delle stanze e ad un personal chef che ogni mattina preparerà la colazione/brunch. A tua disposizione anche percorsi di trekking sui laghi privati della tenuta e su richiesta massaggi e corsi di cucina.

Luxe

A vibrant coastal scene captures lush greenery and colorful flowering plants in the foreground, framing a serene view of a small island surrounded by calm blue waters. The clear sky provides a picturesque backdrop, enhancing the natural beauty of this seaside landscape.

Villa

The View Experiences - A window to the Tuscan sea

On the marvelous coast of Tuscany in the charming town of Porto Ercole between two Spanish Fortresses of the XVI century appears this classic tuscan house where you can spend an unforgettable holiday with your family and friends. After a blooming garden full of flowers your attention will be captured by a large breathtaking terrace with an amazing sea view, together with a salted water pool and of course a very elegant home in a tuscan style with all modern amenities and comforts.

Luxe

A serene outdoor area features a stone wall bordering a wooden deck with loungers. Three sun loungers, cushioned in soft white, are arranged for relaxation. A robust tree offers shade, while a Tuscan villa stands in the background amid a lush, green lawn.

Villa

Villa Zen

Get a sense of serenity at this Tuscan villa. Italy’s rural landscape sprawls around the property with verdant lawn and lush, towering trees. A gym keeps wellness at the forefront of your stay. There are two pools to choose from: an infinity-edge in the garden and a heated option indoors. Explore the surrounding areas on foot or bike. You’ll discover beaches nearby as well as world-class wineries. Copyright © Luxury Retreats. All rights reserved.

Luxe

An infinity pool with a clear water surface extends towards the horizon, surrounded by lush green grass. A wooden pergola provides shaded seating, while rolling hills are visible in the background under a soft sky.

Villa

Villa Ranuncolo

Rustic and renovated stone villa near Pienza Soak in a gardenside tub under the Tuscan sky at this pastoral hillside villa. Brick archways, a stone facade, and terracotta walls form the Italian backbone, while the infinity pool, terrace, and cavernous games room add a more modern kick. Dine with a party of 14, recline by the fireplace, and taste the famous cheeses of Pienza and wines of Montalcino and Montepulciano in this sightseeing mecca.

Luxe

Villa

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.

Luxe

A spacious terrace is showcased, framed by large potted plants and surrounded by sea views. The building features a modern design with large windows, allowing natural light to enhance the outdoor space, which is ideal for relaxation.

Place to stay

Orietta

From its prime location on Monte Argentario, Villa Orietta enjoys idyllic sea and countryside views, as well as proximity to some of Tuscany’s most intriguing villages. With space for 14 guests, a lush garden, and authentic Italian architecture, this villa is perfect for special occasions. When you’re not out exploring Tuscany, enjoy alfresco meals on the ocean view terrace. Copyright © Luxury Retreats. All rights reserved.

Luxe

An aerial view showcases the villa set amidst rolling hills, surrounded by lush vineyards and greenery. A swimming pool reflects the sunlight, while the landscape extends toward distant mountains, creating a serene backdrop for relaxation.

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Villa di Montesoli

Situated in a dominant position, Villa di Montesoli, overlooks Montalcino and Castiglion Del Bosco on one side and the Val d'Orcia on the other. Immersed among vineyards, olive threes and organic wheat fields, this Villa of new renovation offers maximum comforts in over 900 sqm. There are 9 bedrooms all with an ensuite bathroom, ideal for groups up to 18 people. Air Conditioning in every single room.