Luxury rentals in Siena

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.

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

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.

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 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.

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.

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 in 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.

Casalberna 14

Casalberna is nestled in the Unesco site of the Val d’Orcia area near the pretty and historic thermal spring town of San Casciano dei Bagni located in southern Tuscany. The property is 2km from the town and only a 15-20 minute walk, enjoyable ebike trip or a short drive.

Le Pratola

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