Luxury rentals in Grosseto

Villa Palazzetta

Wake up early to catch the morning sun as it hits the mist in Val d’Orcia, turning the entire valley gold. You’ll have quite the view from this 5-acre hilltop villa 7-minute’s walk from Montalcino’s center. When the mist settles, set out to explore the property’s private vineyard and olive grove. Then, walk into town for breakfast. And, make sure to pick up some Brunello di Montalcino for later.  Lovingly-restored, this 1600’s farmhouse has been updated with a state of the kitchen, in-floor heating and cooling, and the highest-end electronics and appliances. Staying true to its roots, Villa La Palazetta also boasts a private cantina and wine cellar, wood-burning pizza oven, and rustic fire pit. Dine outside amongst the mountain views. After dinner, issue a challenge on the night-lit bocce court.  Make that home-cooked meal extra-special and get the concierge to book an in-house Italian cooking lesson. The professional kitchen is the perfect place to learn how to hand-make pasta and combine fresh local produce. When the party inevitably moves to the terrace, cool off in the swimming pool, or sample the finest local wines around the alfresco dining set.  Rather dine out? Walk into Montalcino and wander within their historic city walls, where high-quality restaurants, bakeries, and gelato shops line the streets. Take a day trip to Siena and explore the museums, galleries, and churches of the ancient Renaissance city. And, wine tours of the World-famous Brunelle Vineyards are a great way to see all the different areas and landscapes of Val d’Orcia. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary : King size bed, Ensuite bathroom with stand-alone rain shower and bathtub, Safe • Bedroom 2: King size bed, Ensuite bathroom with stand-alone rain shower    • Bedroom 3: 2 Twin size beds, Ensuite bathroom with stand-alone rain shower, Safe • Bedroom 4: Double size bed, Ensuite bathroom with stand-alone rain shower, Safe   OUTDOOR FEATURES • Pergola  STAFF & SERVICES Included • Firewood for outside pizza oven  • Welcome gift • More under “What this place offers” below Extra cost (advance notice may be required): • Activities and excursions • Wine tasting  • Babysitting • Cooking classes  • More under “Add-on services” below

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

Castello di San Lorenzo by Secret Hills

A beautiful waterfall pool with a beautiful sea view of the Tuscan archipelago and the proximity to Bolgheri, a famous Tuscan wine area, reinforce the uniqueness of the Castello di San Lorenzo. The complex restoration of the Castle (1100 AD) has given rise to an oasis that offers splendid views of the Etruscan coast and the surrounding vineyards and olive groves. Comfort and elegance are the protagonists of the structure, from the kitchen to the living room, from the sleeping area to the bathrooms, magnificent garden with centuries-old oaks.

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.

Borgo Continuum

This remarkable hamlet, located in the rolling hills of Magliano in Toscana, is an architectural regeneration project that represents a rare balance between the preservation of rural heritage and contemporary design language. The development has been awarded the Regula Award 2025 for Contemporary Italian Architecture and the LIV Hospitality Design Award, prestigious recognitions celebrating the quality of its restoration and its sensitive, innovative interpretation of the surrounding landscape

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.

I Terzi d'Ombrone Estate-Villa with private pool

Beautifully renovated villa with heated pool located on a 700-hectare private estate. By renting it, you can enjoy an immersive experience in the rhythms and evocative atmosphere of the Maremma. We will take care of your stay in every detail thanks to the daily room cleaning service and a personal chef who will prepare breakfast/brunch every morning. Hiking trails on the private lakes of the estate are also available, as well as massages and cooking classes upon request.

Villa Oliveto

Nestled in the heart of Tuscany, Villa Oliveto offers a luxurious escape with breathtaking views of the Val d'Orcia. The villa features three elegant apartments with kitchens and living rooms, 9 bedrooms, and 9 bathrooms, accommodating up to 18 guests. Outside, guests can relax in two panoramic pools and expansive gardens, perfect for al fresco dining. The 5,000 m² garden can host events for up to 80 people, combining comfort, privacy, and the timeless charm of Tuscany.

Luxury Tuscan Villa with Pool & Spa

The Pieve di San Giovanni is a refuge of beauty and serenity, where history and modernity come together in an unforgettable experience. Set in the enchanting scenery of the Val di Cecina, on the edge of the tiny village of Lustignano (900 m), between the area of the Bolgheri wine cellars and the beaches of Baratti, San Vincenzo and Populonia, the Pieve di San Giovanni enjoys a fortunate hillside position 390 m above sea level and dominates an open viewpoint on every side.

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 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.

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.