Luxury rentals in Asciano

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Top-rated luxury vacation rentals in Asciano

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Luxe

Villa in Radda in Chianti

4.87 out of 5 average rating, 15 reviews

Villa Montemaggio

The Tuscan sun soaks into the stone walls of this 17th-century farmhouse—and into the grapes clustered in the organic vineyards in the surrounding Chianti countryside. The Roman road from Siena to Florence once traced these hills; today, they’re home to the 70-hectare Montemaggio estate, which produces organic wine and olive oil. Siena is 40 minutes away by modern road; Florence, 1 hour. Smell the flowers in the gardens, pick fresh mulberries and figs to snack on, and see if you and the kids can find the playhouse hidden away on the estate’s grounds. There’s a private gym for workouts, a swimming pool for refreshment, and a rooftop terrace just made for the evening’s first bottle of local wine. While the villa still has some of its 17th-century farmhouse charm—spot beamed ceilings, doorways framed in elaborate molding, and a wide hearth on the living room fireplace—it’s been fully renovated. A pair of plump sofas invites you to stay a while in the living room, and there are plenty of chairs around the dining table that takes center stage in the fully equipped kitchen. Learn more about the Montemaggio estate by booking a cooking class, featuring fresh produce from the gardens, or a wine tour. Be sure to ask about the festivals in nearby villages, which range from celebrations of wine to a fete dedicated to bruschetta. Beyond Tuscany’s medieval towns and fortresses, the cities of Siena and Florence are close enough for a day trip. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone rain shower & bathtub, Dual vanity, Bidet, Television, Desk • Bedroom 2: King size bed, Ensuite bathroom with stand-alone rain shower, Television • Bedroom 3: Queen size bed, Ensuite bathroom with stand-alone rain shower, Bidet, Television, Desk FEATURES & AMENITIES • 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 Chiusdino

Quercia

Step outside each morning to feel the warm, fresh breeze as you stroll through fruit gardens and forests of oak at this traditional farmhouse estate in the heart of Tuscany. Embark on day trips to nearby villages, vineyards, and the famous Abbey of San Galgano. Return home for an afternoon swim, a delicious alfresco dinner, and a night of incredible Italian wine by the fireplace. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM Main House • Bedroom 1 - Primary: King size bed, Ensuite bathroom with shower/bathtub combo, Bidet • Bedroom 2: King size bed, Ensuite bathroom with stand-alone rain shower, Bidet, Balcony • Bedroom 3: 2 Twin size beds (can be converted to a king), Day bed, Ensuite bathroom with stand-alone rain & steam shower, Bidet House 2 • Bedroom 4: King size bed, Ensuite bathroom with shower/bathtub combo, Bidet, Walk-in closet, Sofa, Desk • Bedroom 5: King size bed, Shared access to hallway bathroom, shower/bathtub combo, Dual vanity, Bidet, Desk • Bedroom 6: 2 Twin size beds (can be converted to a king), Ensuite bathroom with stand-alone rain & steam shower, Bidet, Walk-in closet, Desk • Bedroom 7: 2 Twin size beds (can be converted to a king), Ensuite bathroom with stand-alone rain shower, Bidet, Walk-in closet OUTDOOR FEATURES • Outdoor living space STAFF & SERVICES Included: • Linen change - twice per week • Concierge service Extra Cost (advance notice may be required): • Activities and excursions • Additional housekeeping

Luxe

Villa in Radicofani

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

Villa in Cetona

5 out of 5 average rating, 22 reviews

Luxury Villa Justina Tuscany

Villa Justina is a hilltop sanctuary set on 30 private acres of vineyards and olive groves—ideal for luxury travelers and families seeking serenity and style. The villa combines designer Italian furnishings, curated contemporary art, and timeless antiques. Recently transformed into a private residence, it offers five-star comfort with new premium bedding, linens, and kitchenware. Services are designed to meet the highest standards, including cleaning and options to add private cook or chef.

Luxe

Villa in Casole d'Elsa

5 out of 5 average rating, 5 reviews

Villa Sublimis by Villas in Med

This is not just any former stone farmhouse, it’s a unique and elegant villa, that stands as a testament to timeless charm fused with modern luxury. Originally built in the 19th century, this magnificent holiday destination has been expertly transformed to preserve its historical allure while offering an array of contemporary comforts. Nestled amidst the rolling, green Tuscan hills west of Siena, it serves as a serene oasis, perfect for those seeking a one-of-a-kind vacation experience.

Luxe

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.

Luxe

Villa in San Gimignano

5 out of 5 average rating, 4 reviews

Villa Sarah Tenuta Melograni

Villa Sarah enjoys spectacular views of the famous towers of San Gimignano. A large garden surrounds the entire structure and also the four-sided infinity pool with spa whirlpool, made with valuable stone of Cardoso, renowned local stone. Next to the swimming pool is a big dependance with large panoramic terrace, equipped outdoor kitchen, bbq, bar area, relaxation area and a large table to enjoy outdoor dining.