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Top-rated vacation rentals in Province of Grosseto

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Luxe

Villa in Buonconvento

Castello di San Bartolomeo

Rising out a verdant Tuscan valley, this delightful and historic castle is set in the idyllic green surroundings of the Val d'Orcia. Fully renovated, the exterior stone turns golden at sunset, with guests free to enjoy the grand rooms, gardens, vineyard, courtyard and poolside lawns. A profusion of charming villages, vineyards and nature reserves are just minutes away, with majestic Siena nearby. Visible from kilometres away, the heights of Castello di San Bartolomeo announce themselves upon the guest from a distance. Entering the welcoming and Italian-tiled foyer, guests will experience a perfect night’s sleep in the huge bedrooms that feature vaulted ceilings and canopy beds. When morning dawns, guests can take in the stunning, rolling hillsides of the protected valley from the villa’s open-air terrace, before exploring the rambling, beautifully maintained gardens, the blue pearl that is the villa’s pool, or the perfectly-maintained tennis court. The stone, ivy-lined walls of the impressive inner courtyard make for a perfect oasis of peace, with the afternoon warmth emanating around the shaded alfresco table. This villa is surrounded by a wealth of day-trip options. Guests can taste the riches of the vineyard and visit the impressive wine cellars that buttress the castle, or venture a few minutes away to the charming medieval streets of the village of Buonconvento. To the east, the forest paths and impressive viewpoints of two nature reserves make for excellent hiking and family outing options. The Renaissance-splendor of Siena is on full display less than 30 minutes to the north, with the town’s stunning central square and UNESCO-protected architecture providing a jaw-dropping example of Italy’s rich history. After a day spent exploring the riches of the countryside, return to the huge interior dining space of the castle to savor a hearty Italian meal, before taking a rich glass of Sangiovese on the moonlit terrace. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with shower/bathtub combo, Dual vanity, Bidet, Air conditioning, Desk, Fireplace, Private balcony, Garden view • Bedroom 2: Queen size bed, Shared access to hallway bathroom, Shower/bathtub combo, Bidet, Air conditioning, Fireplace • Bedroom 3: Queen size bed, Ensuite bathroom with shower/bathtub combo, Bidet, Air conditioning, Desk, Fireplace • Bedroom 4: 2 Twin size beds (can be converted to a king), Ensuite bathroom with shower/bathtub combo, Bidet, Air conditioning, Fireplace Sophia Suite • Bedroom 5: Queen size bed, Ensuite bathroom with shower/bathtub combo, Bidet, Air conditioning, Office space, Crib, Fireplace Tower Suite • Bedroom 6: 2 Twin size beds, Ensuite bathroom with shower/bathtub combo, Bidet, Air conditioning, Lounge area, Television, Fireplace Family Suite • Bedroom 7: King size bed, Shared access to bathroom with Bedroom 8, Shower/bathtub combo, Bidet, Air conditioning, Fireplace • Bedroom 8: 2 Twin size beds (can be converted to a king), Shared access to bathroom in Bedroom 7, Shower/bathtub combo, Bidet, Air conditioning, Desk, Fireplace OUTDOOR FEATURES • Foosball table • Trampoline • More under “What this place offers” below STAFF & SERVICES Included: • Linen change - on Tuesday and Saturday Extra Cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

Luxe

Villa in Monticiano

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 in Radicofani

Meánrátáil 5 as 5, 11 léirmheas

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

Villa in Montepulciano

Il Tosco

Experience Tuscany in a truly authentic way at Il Tosco. Owned by the same noble family for centuries, this well-preserved historic residence still has a host of original furniture and architectural detail. After a thoughtful renovation to luxury standards, this vacation rental is an incredible mix of the heirloom and modern, all in the medieval heart of Montepulciano. You’ll be welcomed to Il Tosco with a basket of wine, juice and homemade cantucci, or almond cookies. Start each morning of your holiday with a cup from the espresso machine, finish with a glass from the wine fridge, and, in between, enjoy amenities like a TV, sound system and Wi-Fi. The villa is a private retreat bursting with charm and character. Step through its richly paneled wooden doors and into beautifully restored interiors with classic cotto floors, beamed ceilings and antique accent pieces. But there are playful touches of modern decor as well, from the Lucite table in the living room and space-age chandelier in the stately dining room to the state-of-the-art appliances in the fully equipped kitchen. Named for Italian poets and composers, the four bedrooms at Il Tosco will impress with en-suite bathrooms and details like ceiling frescoes, vintage family portraits and marble-topped vanities. There are two bedrooms with king beds, including a stunning master suite with a jetted tub, and two with queen beds. Tucked into the historic center of the hilltop town of Montepulciano, Il Tosco is the perfect base from which to delve into Tuscany’s culture and cuisine. Nearby sights include the elegant Chiesa di San Biagio church, the Porta al Prato gate, which heralds the start of the town’s main street, and the inviting Giardino di Poggiofanti park. Stroll the town’s winding streets, stopping off for honeymoon-worthy dinners or samples of local wine, or drive through the countryside to the great cities of Tuscany and Umbria, from Siena to Perugia. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Dante: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Jetted Tub, Television, Air conditioning, Safe • Poliziano: King size bed, Ensuite bathroom with stand-alone shower, Television, Air conditioning, Safe • Puccini: Queen size bed, Ensuite bathroom with stand-alone shower, Television, Air conditioning, Safe • Verdi: Queen size bed, Ensuite bathroom with stand-alone shower, Television, Air conditioning, Safe FEATURES & AMENITIES • Wine fridge • More under “What this place offers” below STAFF & SERVICES Included: • Juice and homemade biscuits upon arrival • Welcome basket including a bottle of wine and homemade cantucci • More under “What this place offers” below Extra cost (advance notice may be required): • Continental breakfast • Personal tour guide • Personal shopper • Activities and excursions • Wine tasting led by a sommelier • Cooking classes • Additional bedding

Luxe

Villa in Radicofani

Villa Colombaiolo

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

Villa in Val D'Orcia

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. Copyright © Luxury Retreats. All rights reserved.

Luxe

Villa in Porto Ercole

The Luxe View Porto Ercole

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

Villa in Capalbio

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

Villa in Montepulciano

Meánrátáil 5 as 5, 6 léirmheas

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

Áit le fanacht in Orbetello

Torre delle cannelle

Perched on the oceanside cliffs of Maremma National Park, this 15th-Century Spanish tower captures soaring views of the Tuscan Sea and enjoys direct access to a breathtaking pebble beach. After a morning swim, spend the day reading in the lush gardens, visiting Tuscany’s most prestigious wineries, and exploring the park’s historic trails by horseback. Copyright © Luxury Retreats. All rights reserved.

Luxe

Villa in Buonconvento

Villa Il Poggino

Recently renovated, this 17th-Century red-brink farmhouse enjoys an authenticity that most vacation rentals simply cannot possess. Spend your days gazing out over the rolling hills of Tuscany, exploring endless pathways, and relaxing in the pool or hot tub. You could also set out to explore Siena and Pienza or go on a truffle hunting tour. Copyright © Luxury Retreats. All rights reserved.