Luxury rentals in Grosseto

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)

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

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

Tenuta Val D’Orcia

EXCLUSIVE VAL D’ORCIA Perched on a hilltop with breathtaking views over the Val d’Orcia, this extraordinary luxury villa—featured in the renowned interior design magazine AD (Architectural Digest)—is the perfect blend of tradition and modernity. Nestled in one of Tuscany’s most iconic areas, known for its rolling hills and postcard-perfect landscapes, the property offers an exclusive retreat for those seeking privacy, relaxation, and an authentic experience in a refined, one-of-a-kind setting.

5* Villa With Outdoor Hot Tub (4B)

This unique villa features a bright living room with bio-ethanol fireplace, Italian-designed kitchen, and spacious terrace with BBQ and hot tub overlooking the golf course. The villa includes a master suite with en-suite and closet, plus three more double bedrooms and three more bathrooms. Guests enjoy full access to the 5*-amenities of Argentario Golf & Wellness Resort: daily breakfast, housekeeping, spa, padel and tennis courts, private parking. Golf carts are available to reach the villa.

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.

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.

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.

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.