Luxury rentals in Asciano

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.

Hospitality · View · Location · Decor · Kitchen · Outdoor spaces · Cleanliness · Comfort · Family · Accuracy · Indoor spaces · Getting around · Sleep quality · Pool · Condition · Nearby · Laundry · Walkability · Air conditioning · Check-in · Amenities

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

Hospitality · Family · Indoor spaces · Location · Pool · Decor · Outdoor spaces · Kitchen · Amenities · Comfort · Nearby · View · Cleanliness · Breakfast · Getting around · Sleep quality · Bathroom · Air conditioning · Accuracy · Quiet · Wifi · Laundry · Condition · Access · Value

Villa Eterna, Tuscan Haven in the Heart of Chianti

VILLA ETERNA - RADDA IN CHIANTI Only a five-minute walk from Radda in Chianti, the villa is set just outside the charming village. Surrounded by rolling vineyards, and postcard-perfect valleys, the villa offers spectacular views across the Florentine hills. Guests can walk to Radda for shops, restaurants, wine bars, and essential services, while the central Chianti location makes day trips to Florence, Siena, San Gimignano, Volterra, Montalcino, and other Tuscan highlights wonderfully easy.

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.

Hospitality · Outdoor spaces · Location · Pool · View · Indoor spaces · Family · Getting around · Condition · Accuracy · Nearby · Cleanliness

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.

Hospitality · Family · Location · Amenities · Pool · View · Outdoor spaces · Decor · Hot tub · Indoor spaces · Cleanliness · Accuracy · Breakfast · Getting around · Condition · Kitchen · Value · Nearby

Villa Mandorla by My Villa Collection

Villa Mandorla, a beautifully restored estate dating back to around 1000 AD, offers a luxurious countryside escape in the heart of Tuscany. This historical property features a central farmhouse and two converted barns, with a total of 7 bedrooms and 7 bathrooms. The villa combines the charm of the past with modern comforts, making it an ideal retreat for families or groups. The expansive grounds include lush gardens and multiple outdoor lounges and dining areas.

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.

Hospitality · View · Location · Indoor spaces · Accuracy · Comfort · Getting around · Decor · Kitchen · Cleanliness · Walkability · Pool · Condition · Value · Outdoor spaces · Bathroom · Grill · Heating · Wifi · Nearby · Family · Long stay · Breakfast · Hot tub · Air conditioning

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.

Hospitality · Pool · Breakfast · View · Nearby · Location · Getting around · Indoor spaces · Biking · Family

NEW - Modern, luxuries Villa (close to Florence)

The entire house is exclusively yours. Perfect for large groups of friends, colleagues, or families with children, parents, and grandparents who want to stay together in peace. From here you can explore Florence for shopping, art, and culture, or enjoy Tuscany’s wine regions. The pool sits close to the house for easy relaxation. Cooking evenings or guided tours can be arranged and we’re happy to help with events or wine tastings.

Hospitality · Pool · View · Indoor spaces · Bathroom · Amenities · Condition · Location · Kitchen · Comfort · Decor · Accuracy · Sleep quality · Value · Air conditioning · Cleanliness · Family

Villa of Montesoli

Situated in a dominant position, Villa di Montesoli, overlooks Montalcino and Castiglion Del Bosco on one side and the Val d'Orcia on the other. Immersed among vineyards, olive threes and organic wheat fields, this Villa of new renovation offers maximum comforts in over 900 sqm. There are 9 bedrooms all with an ensuite bathroom, ideal for groups up to 18 people. Air Conditioning in every single room.

View · Hospitality · Outdoor spaces · Cleanliness · Pool · Kitchen · Indoor spaces · Decor · Getting around · Condition · Bathroom · Nearby · Family

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.

Hospitality · Outdoor spaces · View · Pool · Family · Location · Indoor spaces · Cleanliness · Comfort · Decor · Bathroom · Condition · Getting around · Amenities · Kitchen · Sleep quality · Accuracy · Nearby · Quiet · Layout · Air conditioning · Biking · Pets · Long stay · Backyard · Access · Value