Luxury rentals in Asciano

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Top-rated luxury holiday rentals in Asciano

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Luxe
The villa is set amidst lush greenery and features a modern outdoor swimming pool. Stone facades and large windows characterize the structure, which is surrounded by well-maintained gardens and tall cypress trees. Sun loungers are positioned beside the pool, inviting relaxation.
Villa
4.82 out of 5 average rating, 11 reviews

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

Luxe
The outdoor area features a private swimming pool surrounded by wooden decking and sun loungers. Towering cypress trees are visible, along with a cozy gazebo. The farmhouse blends rustic architecture with modern amenities, set against a clear blue sky.
Villa

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

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.

Luxe
An expansive view showcases the 17th-century farmhouse surrounded by lush vineyards and rolling hills. Soft evening light illuminates the outdoor areas, highlighting trees and garden paths. The landscape, with its blend of greenery and stone architecture, creates a serene setting in the Chianti countryside.
Villa
4.89 out of 5 average rating, 18 reviews

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.

Luxe
The villa is viewed from the swimming pool, surrounded by landscaped gardens. Comfortable sun loungers are arranged on the poolside, with umbrellas offering shade. The serene water reflects the sky, while the rustic stone exterior of the villa provides a charming backdrop.
Villa
5 out of 5 average rating, 7 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
The exterior of the villa features a rustic stone façade and a spacious patio with a dining table. Lush green lawns and trees frame the property, while decorative planters and modern light orbs enhance the outdoor space. A pathway leads to the entrance, inviting guests in.
Villa in Sartenao
5 out of 5 average rating, 25 reviews

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.

Luxe
The villa is situated in a lush, green landscape, surrounded by rolling hills and vineyards. The exterior features a yellow stone facade with a terra cotta roof, framed by well-maintained gardens filled with olive and cypress trees. A swimming pool and outdoor seating area are visible.
Villa
4.85 out of 5 average rating, 13 reviews

Villa Chianti Fornace

Experience the epitome of Tuscan luxury at Villa Chianti Fornace — a meticulously restored historic villa nestled between Florence and Siena. This exquisite retreat features expansive gardens, a private spa, and a panoramic pool with sweeping views of rolling vineyards. Whether you're planning a romantic escape or a family holiday, immerse yourself in the authentic charm and serene beauty of the Chianti countryside at this unparalleled haven.

Luxe
Villa
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
An infinity pool, crafted from Cardoso stone, offers a view overlooking lush vineyards and rolling hills. The historic towers of San Gimignano are visible in the distance, framed by the vibrant landscape under a clear blue sky.
Villa
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.

Luxe
A spacious outdoor pool is surrounded by lush greenery and lounge chairs. The villa's rustic structure, with cypress trees and terracotta roof, is visible in the background against a clear evening sky, reflecting warm hues in the water.
Villa
5 out of 5 average rating, 7 reviews

Sole del Chianti

Halfway between Florence and Siena, among the verdant hills and the vineyards of Tuscany, stands the resort “Sole del Chianti”, where the sound of nature prevails along with silence and privacy. Here it’s still possible to experience the country life of times gone by.

Luxe
The rustic exterior of the villa features a mix of brick and plaster, with a sloped tile roof. Lush greenery surrounds the property, while a gravel pathway leads to a shaded seating area under a tree, inviting relaxation in the serene countryside.
Villa
4.67 out of 5 average rating, 6 reviews

Farmhouse on top wine estate in Montepulciano

Please note this Host requires a supplemental contract to be signed at the time of booking.

Luxe
An outdoor seating area features a stone floor and is shaded by a wooden pergola. In the background, a heated infinity pool overlooks rolling hills and lush vineyards, with tall trees and green grass framing the scene. Lanterns are positioned on either side for ambiance.
Villa
5 out of 5 average rating, 5 reviews

Le Pratola

Note: The property has gates and security cameras. All security cameras are external.

Popular amenities for Asciano luxury holiday rentals

Destinations to explore

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  3. Tuscany
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