
Luxury rentals in San Gimignano
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Top-rated luxury holiday rentals in San Gimignano
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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.

Villa Simone
Villa Simone, a 15th-century stone villa near San Gimignano, has been beautifully restored, offering rustic Tuscan charm and 6 bedrooms for up to 12 guests. Surrounded by vineyards and olive groves, it features a spacious garden, a pool with Chianti hill views, and a tennis court. This estate produces exceptional olive oil and wines, including Vernaccia di San Gimignano, making it perfect for relaxation and exploring nearby medieval villages and iconic cities like Florence, Siena, and Pisa.

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 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.

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.

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.

Villa di Tizzano between Chianti and Florence
Surrounded by olive trees and vineyards in the Chianti Classico region, this stunning property is adorned with a tower, a romantic park, and French gardens that enjoy sweeping views of the rolling Italian hillside. When you’re not relaxing by the pool or enjoying alfresco meals on the terrace, venture out on day trips to Florence, Siena, Pisa, and other incredible Tuscan cities. Copyright © Luxury Retreats. All rights reserved.

Luxury Apartment 'Caterina da Siena'
Overlooking Duomo, Via del Corso, and Via dello Studio, this classic Florence apartment is a luxurious home base for your next exciting vacation. From the heart of Florence, you’ll have no trouble getting around to all of the city’s world-famous sites, many by foot. The apartment is decorated with custom furnishings, underfloor heating, and fine Florentine finishes. Copyright © Luxury Retreats. All rights reserved.

Villa Finesterra
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.

Cinque Cipressi 8, Emma Villas
Hidden amongst the woods and just a few minutes from the medieval borgo of Montecatini Val di Cecina, Cinque Cipressi, an elegant house dating back 7 century and fruit of refined renovation, is a special refuge in which to immerse yourself in relaxing tranquillity and discover secrets of Tuscany off the beaten path-known.

Sole del Chianti
Halfway between Florence and Siena, among the verdant hills and the vineyards of Tuscany, stands the resort “Sole del Chianti”, where the sound of nature prevails along with silence and privacy. Here it’s still possible to experience the country life of times gone by.

Duchessa Sofia -La Dimora degli Affreschi Florence
Our Florence palazzo restoration has finally reached fruition near the banks of the Arno in the thriving district of Santa Croce
Popular amenities for San Gimignano luxury holiday rentals
Other great luxury holiday rentals in San Gimignano

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Luxury 8 bed villa near Florence with heated pool

Villa Sublimis by Villas in Med

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- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Strozzi Palace
- Santa Maria Novella
- Ponte Vecchio
- Basilica Di San Miniato A Monte
- Marina di Cecina
- Porta Elisa
- Del Chianti
- Basilica of Santa Maria Novella
- Mercato Centrale
- Eremo Di Camaldoli
- Pisa Centrale Railway Station
- Cala Violina
- Great Synagogue of Florence
- Piazza del Duomo (Pisa)
- Fortezza da Basso
- Spiagge Bianche
- Uffizi Gallery
- Piazza della Repubblica
- Piazzale Michelangelo
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Pitti Palace
- Parco delle Cascine
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