Luxury rentals in San Gimignano

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Top-rated luxury holiday rentals in San Gimignano

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Luxe

Villa

Villa Rinascimento

Perched atop the hills of Firenze, this villa acts more like your own boutique hotel with 1 large pool and space for 36 guests. The alfresco dining area on the terrace is perfect for large gatherings, and the sweeping view of the city below is an unbeatable backdrop. To truly relax, visit the brick-walled spa in the basement and slide into the rejuvenating whirlpool. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM The main villa • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower • Bedroom 2: King size bed, Ensuite bathroom with stand-alone shower • Bedroom 3: 2 Twin size beds (can be converted to a king), Ensuite bathroom with stand-alone shower • Bedroom 4: King size bed, Ensuite bathroom with bathtub • Bedroom 5: 2 Twin size beds (can be converted to a king), Ensuite bathroom with stand-alone shower The Fattoria • Bedroom 6: 2 Twin size beds (can be converted to a king), Ensuite bathroom with stand-alone shower • Bedroom 7: King size bed, Ensuite bathroom with stand-alone shower • Bedroom 8: Queen size bed, Ensuite bathroom with stand-alone shower • Bedroom 9: Twin size bed, Ensuite bathroom with stand-alone shower The Bottega • Bedroom 10: King size bed, Ensuite bathroom with stand-alone shower • Bedroom 11: King size bed, Ensuite bathroom with bathtub The Studio • Bedroom 12: Double size bed, Ensuite bathroom with stand-alone shower • Bedroom 13: Double size bed, Ensuite bathroom with stand-alone shower • Bedroom 14: Double size bed, Jack & Jill bathroom shared with Bedroom 15 • Bedroom 15: Twin size bed, Jack & Jill bathroom shared with Bedroom 14 The Frantoio • Bedroom 16: Twin size bed, Jack & Jill bathroom shared with Bedroom 17 • Bedroom 17: Twin size beds (can be converted to a king), Jack & Jill bathroom shared with Bedroom 16 • Bedroom 18: Twin size beds (can be converted to a king), Ensuite bathroom with stand-alone shower • Bedroom 19: Double size bed, Ensuite bathroom with stand-alone shower • Bedroom 20: Double size bed, Ensuite bathroom with stand-alone shower OUTDOOR FEATURES • Whirl pool - unheated STAFF & SERVICES Included • Linen change - twice per week • Concierge service (9 AM – 7 PM) • Daily Breakfast

Luxe

Villa

4.89 out of 5 average rating, 18 reviews

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.

Luxe

Place to stay

4.67 out of 5 average rating, 3 reviews

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.

Luxe

Villa

5 out of 5 average rating, 7 reviews

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.

Luxe

Flat

5 out of 5 average rating, 3 reviews

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.

Luxe

Villa

5 out of 5 average rating, 3 reviews

Villa Iris Tenuta Melograni

The villa itself was once a brick workshop and dates back to 1737. Thanks to a careful restoration, it’s now comfortable and chic, with traditional details like cotto floors and beamed ceilings set off by casual modern furnishings in the living and dining rooms. The fully equipped kitchen expertly pairs rustic cabinetry with state-of-the-art appliances and Carrara marble surfaces to stunning effect.All six bedrooms have en-suite bathrooms and air conditioning.

Luxe

Villa

4.85 out of 5 average rating, 13 reviews

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.

Luxe

Home

5 out of 5 average rating, 5 reviews

Luxury Diamond in the Hills-Private Pool & Jacuzzi

Benvenuti a Villa La Fonte, un rifugio esclusivo immerso nel cuore delle colline toscane, dove il fascino rustico incontra il comfort moderno per offrire un’esperienza senza pari. Questa straordinaria proprietà, è il luogo perfetto per chi desidera rigenerarsi nella quiete della natura, senza rinunciare all’eleganza e al benessere. Da metà ottobre sarà disponibile anche la sauna, per aumentare il benessere durante il soggiorno invernale!

Luxe

Villa

5 out of 5 average rating, 3 reviews

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.

Luxe

Place to stay

5 out of 5 average rating, 5 reviews

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.

Luxe

Villa

5 out of 5 average rating, 8 reviews

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.