
Luxury rentals in Asciano
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Top-rated luxury vacation rentals in Asciano
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Villa Conti Galgani
Located in the heart of the Tuscan countryside, between Florence and Rome, just 70km from Siena, Villa Conti Galgani is a charming estate, immersed in 65 hectares of hilly countryside, among olive groves and gardens. The villa has 7 suites, each characterized by an individual style, inspired by the rich history of the estate. Conti Galgani is the perfect place for those who want to spend a relaxing holiday in the Tuscan countryside, equipped with an outdoor swimming pool, a gym, an indoor hydro-massage pool and a billiard room. Handcrafted furniture and a modern eye for color breathe new life into this 16th-century former convent set between Tuscany’s Val di Chiana and Val d’Orcia. Olive groves and a lawn surround the outdoor pool and for-the-picking vegetable garden, and inside there’s a second pool and a games room. It’s 20 kilometers to Renaissance architecture in Pienza and hot springs in San Casciano dei Bagni. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone rain shower, Dual vanity, Bidet, Television, Countryside view • Bedroom 2: King size bed, Ensuite bathroom with stand-alone rain shower, Bidet, Air extractor, Countryside view • Bedroom 3: King size bed, Ensuite bathroom with stand-alone rain shower & bathtub, Dual vanity, Bidet, Countryside view • Bedroom 4: Queen size bed, Ensuite bathroom with stand-alone rain shower, Bidet • Bedroom 5: 2 Twin size beds, Ensuite bathroom with stand-alone rain shower, Bidet, Air extractor, Television • Bedroom 6: King size bed, Day bed, Ensuite bathroom with stand-alone rain shower & bathtub, Bidet, Air extractor, Television, Mountain view • Bedroom 7: Queen size bed, Ensuite bathroom with stand-alone rain shower, Bidet STAFF & SERVICES Extra Cost (advance notice may be required): • Activities and excursions

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.

Villa Montemaggio
This booking is a chance to stay in a real Tuscan Farmhouse that is situated inside an actual vineyard. Its a private property of the owners of the estate, completely refurbished to give every possible comfort but still live in the middle of nature. The setting is absolutely breathtaking amongst the rolling tuscan hills, far away from the noise of the concrete jungle and busy streets. Here the only noise you will hear is the chirping of the birds or faraway hum of the tractor in the fields.

Luxury Villa Tuscany
An exclusive estate 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.

La Tuscia - Tenuta di Toscana, Boutique Villa
Casa La Tuscia is a beautifully restored 1700s farmhouse blending original “Pietra” and “Travi” with modern, luxurious interiors. This exclusive-use Luxe Villa is ideal for families, couples, friends, or small business groups. Set in the Tuscan countryside, it’s surrounded by its own vineyards and orchards. Guests enjoy an elegant experience with a serene spa, panoramic heated pool, jacuzzi in the olive grove, daily housekeeping, and high-speed Wi-Fi throughout the estate.

Villa Noce by My Villa Collection
Villa Noce is an enchanting estate nestled in the heart of Chianti, where timeless Tuscan charm meets refined versatility. Designed to host both exclusive private stays and sophisticated events, the villa offers an atmosphere of understated elegance and absolute privacy. On the ground floor, expansive living spaces unfold with effortless flow. A professional-grade kitchen, complete with fireplace and traditional pizza oven, serves as the heart of the home.

Villa Iris Tenuta Melograni
Villa Iris, the result of a meticulous restoration of an ancient brick kiln dating back to 1737, stands in a privileged position on the hill, overlooking the famous towers of San Gimignano. The villa is spread over two elegant floors and is surrounded by a vast, lush garden. It features six luxurious bedrooms, each with a private bathroom, and can accommodate up to twelve guests. The 6 bedrooms en suite all have air conditioning and WiFi.

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.

Velari
Preserving the historical character of the structure through an innovative approach: the design of Villa Volterra has been curated with the intention of creating the right balance between rustic and modern, tradition and design. The beating heart of the property is the living area, which is adorned by a panoramic glass wall with a spectacular view of the swimming pool that creates a seamless bridge to the garden.

Luxury Retreat in the Tuscan Hills
A newly-restored Tuscan villa with stunning views across the Sienese hills. Set amid olive groves in the beautiful Val d’Orcia, the house has been restored to the highest specifications while maintaining its authentic Tuscan style and charm. The main house has 5 bedrooms sleeping 10 guests, and there is an adjacent annex which sleeps up to 4 guests in 2 bedrooms.

Villa Centia San Gimignano
A contemporary villa in the heart of Tuscany, with stunning views over the iconic towers of San Gimignano. From the lush surrounding hills to the understated charm of its rooms, every corner of Villa Centia reveals a timeless beauty that will captivate you from the moment you set foot here.

Nuova - Villa moderna
Brand new location in the heart of the Tuscan vineyards, offering stunning panoramic views and a truly picturesque, exclusive setting. Fully restored to the highest standard and completed in late 2025. only about 25min south of Florence.
Popular amenities for Asciano luxury vacation rentals
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Sole del Chianti

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- Cathedral of Santa Maria del Fiore
- Lake Trasimeno
- Santa Maria Novella
- Santa Maria Novella
- Lake Bolsena
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Cala Violina
- Mercato Centrale
- Parco Regionale Della Maremma
- Uffizi Gallery
- Stazione Santa Maria Novella
- Fortezza da Basso
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Pitti Palace
- Boboli's Garden
- Palazzo Vecchio
- Piazza della Signoria
- Centro Storico Orvieto
- Cascate del Mulino
- Basilica of Santa Croce
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