Luxury rentals in San Gimignano

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.

Piazza di Santa Croce the Magnificent

In the precious silence of Palazzo Barberini, a noble Florentine residence already mentioned in 1531, a huge apartment opens up that tells of centuries of art and beauty. Overlooking Piazza Santa Croce, the beating heart of Florence, a space of over 400 m2 comes to life where Renaissance elegance dialogues with contemporary design. Once the artist's studio of the master Pietro Annigoni (1933-1952), today it is the perfect place to experience the magic of Florence with intensity and beauty.

Villa Medicea Flaherty Events & Retreats

Nestled in the heart of Tuscany, Villa Medicea blends elegance and natural beauty. This 10-bedroom villa offers stunning views, a private infinity pool, jacuzzi, and tennis court. Ideal for large gatherings, it’s set on three hectares of private parkland. A short drive to Lucca, it’s close to iconic Tuscan destinations like Pisa, Florence, and Cinque Terre. Newly restored, it accommodates up to 22 guests, with alfresco dining, a kids' pool, and endless relaxation in a serene environment.

Cavour 83 Prestige House by 360 Rentals

In the historic and residential center of Florence, prestigious 210m2 apartment on the 1st floor with lift located in a beautiful Florentine palace dating from 1880 on the former site of a monastery. The apartment is located in the historic center in a quieter residential area. You can reach the main attractions of the city in 10-15 minutes on foot and 20 of the SMN train station. It is now also possible to reach us directly from Peretola Airport with the T2 tram line in 20/30 minutes.

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.

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.

Umamma - The Ex-Brothel - The Unexpected Place

UMAMMA is a 16th century open space. You will find yourself in an unexpected world embraced by the Florentine hills, from where you can see Leonardo Da Vinci's house. UMAMMA is designed for those who want to rediscover natural energy. In a wonderful square inhabited by local people, UMAMMA is the starting point for visiting Tuscany from one of the most picturesque points. The private heated pool is accessible only to guests of the house, through a secret passage. Enjoy.

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.

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.

2BR • Luxury Florence Penthouse • 360° Panorama

🍷 Savor the Local Flavor: enjoy a complimentary gourmet food and wine tasting when you stay for 3 nights or more. Valid for stays until 31st July 2026 🍷 ⚠️ Review mentioning "noise" ⚠️ Please note that there is no construction work taking place in the building or local area. The review is specific to the summer of 2023 when we first rented the property.

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.

Por Santa Maria terrace

Exclusive apartment in the heart of Florence with a view of Ponte Vecchio. Prestigious large apartment located in Borgo SS Apostoli, on the corner of Via Por Santa Maria, in an absolutely exceptional and prestigious position in the heart of the historic center of Florence.