Luxury rentals in San Gimignano

Florence City View Estate

NEW LISTING! Experience the absolute best of both worlds, the city & the countryside. O:live Villa Firenze is located in a protected area on the Florentine hills with views of the magnificent city of Florence. Nestled between 27 acres of rich landscape with a lovely olive grove that counts more than 1,200 olive trees with its own olive oil production. The villa is the perfect choice for friends and families who seek a contemporary design as well as the privacy & seclusion of the country 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.

Umamma - The Ex-Brothel - The Unexpected Place

UMAMMA, e’ un open space del 1500. Ti troverai in un mondo inaspettato abbracciato dalle colline Fiorentine, da dove potrai osservare la casa di Leonardo Da Vinci. UMAMMA e’ stato pensato per chi ha voglia di ritrovare un’energia naturale. In una piazza meravigliosa abitata da persone locali, UMAMMA e’ il punto di partenza per visitare la Toscana da uno dei punti più suggestivi. La piscina privata riscaldata e' accessibile solo dagli ospiti della casa, tramite un passaggio segreto. Enjoy.

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.

Piazza di Santa Croce il Magnifico

Nel silenzio prezioso di Palazzo Barberini, nobile dimora fiorentina menzionata già nel 1531, si apre un enorme appartamento che racconta secoli di arte e bellezza. Affacciato su Piazza Santa Croce, cuore pulsante di Firenze, prende vita uno spazio di oltre 400 m2 dove l'eleganza rinascimentale dialoga con il design contemporaneo. Un tempo studio d’artista del maestro Pietro Annigoni (1933-1952), oggi è il luogo perfetto per vivere la magia di Firenze con intensità e bellezza.

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.

Luxury de luxe avec SPA en Toscane

The Pieve di San Giovanni is a refuge of beauty and serenity, where history and modernity come together in an unforgettable experience. Set in the enchanting scenery of the Val di Cecina, on the edge of the tiny village of Lustignano (900 m), between the area of the Bolgheri wine cellars and the beaches of Baratti, San Vincenzo and Populonia, the Pieve di San Giovanni enjoys a fortunate hillside position 390 m above sea level and dominates an open viewpoint on every side.

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.

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 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.

Nuova - Villa moderna

Brand new location in the heart of the Tuscan vineyards, offering stunning panoramic views and a truly picturesque, exclusive setting. Fully restored to the highest standard and completed in late 2025. only about 25min south of Florence.