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.

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.

Isola Serena - New Private Luxury Villa in Chianti

Located in Castellina in Chianti in Tuscany, Italy, Isola Serena is a beautiful private luxury villa on 4 acres of land with the most breathtaking views in the Tuscan countryside. Covered in vineyards, olive groves, and captivating forestry, the villa finished restoration in 2014 and expanded in 2023 to include 2 additional guesthouses. The property now has a total of 10 bedrooms all with ensuite bathrooms and can sleep up to 23 people, making this one of the biggest villas in Chianti.

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 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.

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.