Luxury rentals in Asciano

Find and book unique accommodations on Airbnb

Top-rated luxury vacation rentals in Asciano

Guests agree: these stays are highly rated for location, cleanliness, and more.

1 of 1 pages1 / 1
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 in Sarteano

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

HospitalityLocationConditionViewIndoor spacesFamilyAmenitiesOutdoor spacesBathroomGetting aroundPoolBreakfastBackyardKitchenValueLayoutComfortNearbyCheck-inCleanliness

4.83 out of 5 average rating, 12 reviews
Luxe
A serene outdoor space features a clear swimming pool complemented by lounge chairs arranged around its edge. Natural stone walls and lush greenery provide a tranquil backdrop, while rustic buildings can be seen rising from the gently sloping terrain.
Villa in Chiusdino

Villa Quercia by Burghesius

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 San Quirico d'Orcia

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
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

Luxury Villa Tuscany

Exclusive AirBnB Listing. 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 with options to add private cook or chef. Xi

HospitalityFamilyIndoor spacesLocationPoolDecorOutdoor spacesKitchenAmenitiesComfortNearbyViewCleanlinessGetting aroundBreakfastSleep qualityBathroomAir conditioningAccuracyQuietWifiLaundryConditionAccessValue

5.0 out of 5 average rating, 31 reviews
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 in Casole d'Elsa

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.

HospitalityFamilyLocationDecorPoolIndoor spacesViewAccuracyOutdoor spacesKitchenCheckoutQuietComfortCheck-inAmenities

5.0 out of 5 average rating, 10 reviews
Luxe
The villa is beautifully illuminated at dusk, showcasing the infinity pool and spa whirlpool. Comfortable lounge chairs are positioned near the pool, with a panoramic view of the surrounding garden and landscape. The outdoor dependance features seating areas, enhancing the inviting atmosphere of the property.
Villa in San Gimignano

Villa Sarah Tenuta Melograni

The villa is spread over two floors and is immersed in a lush garden that perfectly embodies the beauty of the Tuscan countryside. It features five elegant bedrooms en suite, and can accommodate up to 10 guests in maximum comfort. Outside, there is a dépendance equipped with a designer outdoor kitchen, an exclusive relax area, and a special dining table, perfect for convivial moments under the sky. The 5 bedrooms all have their own private bathroom, air conditioning, WiFi and smart tv.

HospitalityOutdoor spacesLocationPoolViewIndoor spacesFamilyGetting aroundConditionAccuracyNearbyCleanliness

5.0 out of 5 average rating, 5 reviews
Luxe
Home in Gaiole in Chianti

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.

HospitalityFamilyLocationAmenitiesPoolViewOutdoor spacesDecorHot tubIndoor spacesCleanlinessAccuracyBreakfastGetting aroundConditionKitchenValueNearby

5.0 out of 5 average rating, 22 reviews
Luxe
Villa in Barberino Tavarnelle

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.

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 in Radda in Chianti

Villa Montemaggio

Stay in an authentic Tuscan farmhouse set within a working vineyard, surrounded by breathtaking rolling hills. A private property of the estate owners, fully refurbished for modern comfort while preserving its country charm. Far from busy streets, here you’ll hear birdsong and the distant hum of tractors in the fields. Please note: to get to the property you have to drive for about 6 km of unpaved road, part of its secluded countryside setting.

HospitalityViewLocationDecorOutdoor spacesKitchenCleanlinessIndoor spacesFamilyAccuracyComfortPoolGetting aroundSleep qualityNearbyConditionCheck-inBathroomLaundryWalkabilityAccessValueAir conditioningAmenities

4.91 out of 5 average rating, 33 reviews
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 in Barberino Tavarnelle

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.

HospitalityViewLocationIndoor spacesAccuracyComfortGetting aroundDecorKitchenCleanlinessWalkabilityPoolConditionValueOutdoor spacesBathroomGrillHeatingWifiNearbyFamilyLong stayBreakfastHot tubAir conditioning

4.86 out of 5 average rating, 14 reviews
Luxe
Villa in Castellina in Chianti

Villa Castellina, Elegance and Luxury

VILLA CASTELLINA - CHIANTI AREA Villa Castellina is a luxurious property overlooking the beautiful hills of the famous Tuscan countryside of Chianti. This carefully restored estate retains its traditional charm while offering all the modern comforts and amenities expected at a luxury villa. This includes an external private swimming pool, a luxurious spa with a heated indoor-outdoor pool, and a sauna for ultimate relaxation.

Luxe
Villa in Castiglione del Lago

Il Mandorlo by Boutique, Luxury Villa in Umbria

A private six-bedroom country estate with an infinity pool, set on 1.5 hectares on the border of Tuscany and Umbria, near Lake Trasimeno. This newly restored villa blends rural Italian architecture with refined contemporary interiors. With generous indoor and outdoor living spaces, five-star comfort, and optional concierge and chef services, it is an elegant base for gathering, relaxing, and exploring central Italy.

HospitalityDecorPoolBreakfastBathroomKitchenSleep qualityComfortIndoor spacesParkingCleanlinessAmenities

Popular amenities for Asciano luxury vacation rentals

Other great luxury vacation rentals in Asciano

Luxe
A bright dining area features a large wooden table surrounded by eight chairs. Natural light fills the space through arched windows, highlighting rustic brick flooring. Elegant chandeliers add a touch of sophistication, while a decorative vase with flowers sits at the center of the table.
Villa in Montespertoli

Leonardo

HospitalityLocationPoolFamilyOutdoor spacesViewAccuracyGetting aroundIndoor spacesCleanlinessDecorKitchenQuietComfortAmenitiesConditionSleep qualityNearby

5.0 out of 5 average rating, 14 reviews
Luxe
Home in Castellina in Chianti

Isola Serena - New Private Luxury Villa in Chianti

HospitalityLocationViewIndoor spacesGetting aroundPoolComfortAccuracyBathroomAmenities

4.8 out of 5 average rating, 5 reviews
Luxe
Villa in Montepulciano

Villa Benefizio

HospitalityPoolBreakfastViewNearbyLocationGetting aroundBikingIndoor spacesFamily

5.0 out of 5 average rating, 7 reviews
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 in Barberino Tavarnelle

Sole del Chianti

HospitalityIndoor spacesLocationFamilyGetting aroundConditionViewAccuracyOutdoor spacesKitchenNearbyCleanliness

5.0 out of 5 average rating, 8 reviews
Luxe
A sparkling blue pool is surrounded by sun loungers and large umbrellas, set against a backdrop of lush greenery and the hillside villa. Wildflowers add color to the landscape, creating a serene outdoor space for relaxation.
Villa in Radicondoli

Mugnello Radicondoli

PoolHospitalityWalkabilityDecorBreakfastViewOutdoor spacesBathroomKitchenSleep qualityIndoor spacesGetting aroundConditionLocationHikingComfortNearbyFamilyAmenities

5.0 out of 5 average rating, 5 reviews
Luxe
A charming Tuscan farmhouse is set amidst lush greenery, featuring elegant stonework and tall trees. A well-maintained lawn with vibrant flower beds enhances the outdoor space, while a gravel path leads up to the property, inviting exploration of the expansive landscape.
Place to stay in San Gimignano

Villa Simone

PoolIndoor spacesValueConditionTVAccuracyHospitalityOutdoor spacesHot tubCleanlinessBathroom

4.67 out of 5 average rating, 3 reviews
Luxe
Villa in Greve in Chianti

Villa Marcellina

LocationLayoutViewHospitalityCheck-inAmenitiesCheckout

5.0 out of 5 average rating, 3 reviews
Luxe
The image captures a fenced swimming pool with a wooden deck, surrounded by lounge chairs. A rustic farmhouse is visible in the background, set against a vast, open landscape under a clear blue sky dotted with clouds.
Villa in Buonconvento

Villa Il Poggino

DecorComfortPoolHospitalityOutdoor spacesCleanlinessLocationKitchen

Destinations to explore