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Holiday rentals in Castel San Gimignano

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Top-rated holiday rentals in Castel San Gimignano

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Top guest favourite
An aerial view captures the sprawling vineyards and olive groves surrounding Podere Vergianoni. The property features a salt-water pool positioned on a terrace, offering panoramic views of the lush Chianti landscape and medieval castle in the distance. Rustic buildings line the garden area.
Apartment in Noce
5 out of 5 average rating, 184 reviews

Ancient 17th-century farm in Chianti, Tuscany

Podere Vergianoni is an ancient and historic property dating back to the 17th century, located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional style of ancient Tuscany: wooden beams, terracotta floors, and tasteful handcrafted furnishings that will help you enjoy a pleasant stay. In the large outdoor courtyard, you'll find a saltwater swimming pool on a panoramic terrace with wonderful views of the castle, hills and vineyards, and breathtaking sunsets.

Top guest favourite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano
4.99 out of 5 average rating, 145 reviews

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Top guest favourite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home in Gambassi Terme
5 out of 5 average rating, 204 reviews

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Top guest favourite
A charming outdoor seating area is set against a backdrop of rolling green hills. Two green metal chairs and a matching table are surrounded by flowering plants, with cypress trees rising in the distance under a partly cloudy sky.
Apartment in Pienza
5 out of 5 average rating, 136 reviews

Mascagni Farmhouse in Val d'Orcia, Pienza

Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

Top guest favourite
An inviting villa surrounded by lush greenery and vibrant flowers, featuring blooming rose bushes and olive trees. The gravel pathway leads to the entrance, showcasing a two-story structure with balconies. Sunlight highlights the colorful landscape, creating a serene atmosphere.
Villa in Impruneta
5 out of 5 average rating, 163 reviews

The Tower

Ancient Tuscan villa, beautiful, with exclusive private garden, completely renovated, surrounded by the beautiful and gentle Tuscan hills. The villa has a breathtaking view, is very sunny, well furnished and equipped with all amenities, quiet and not isolated. The house is located in Bagnolo, a small hamlet of Impruneta at the gates of Chianti, an area of olive groves, vineyards and peace. The house is about 10 km by car from the center of Florence.

Guest favourite
A serene pool area is framed by lush vegetation, featuring a clear swimming pool surrounded by lounge chairs and umbrellas. The distant hills are visible against a clear blue sky, enhancing the sense of tranquility in this outdoor space.
Flat in Castel San Gimignano
4.87 out of 5 average rating, 70 reviews

Casa Verbena - relax in the heart of Tuscany

Casa Verbena is one of the 4 apartments of the complex "La Casina di Manu". It is located in Castel San Gimignano, a small village in the heart of Tuscany, in a strategic position both to visit among the most important centers of our Region (San Gimignano, Volterra, Siena and Florence) both to be able to take paths on foot or by bike, immersed in an enchanted landscape, dotted with olive groves, vineyards and cypresses.

Top guest favourite
The exterior of the country house is framed by tall, narrow cypress trees and well-maintained gardens featuring various plants. A terracotta pot stands prominently, and gravel pathways lead to the entrance, which is characterized by stone walls and an arched doorway.
Home in Tavarnelle Val di Pesa
4.96 out of 5 average rating, 318 reviews

Casa Al Poggio & Chianti view

Casa al Poggio is a typical country house of Chianti area is spread in 145 square meters on two floors, the ground floor is a large living area, with kitchen and sofa ,fireplace ,up stairs there is 2 large double bedrooms and a sofa bed in the middle open room , always setable as 2 singles or a double bed bed and a relaxing bathroom with shower and bath with Chianti view.

Superhost
An outdoor seating area is presented, featuring a large table surrounded by wooden chairs under a shaded umbrella. Two lounge chairs are positioned on the grassy lawn, with a panoramic view of the surrounding hills and a clear blue sky in the background.
Flat in Castel San Gimignano
4.77 out of 5 average rating, 116 reviews

Girasole large apartment in a Tuscan village

Cozy and spacious apartment in a small Tuscan village in the municipality of San Gimignano. Casa Girasole is located in Castel San Gimignano, a small and ancient village which is 12 km from San Gimignano, 15 km from Volterra, 30 km from Siena and 50 km from Florence and 50 km from the Tyrrhenian Sea.

Top guest favourite
An inviting outdoor area features a serene swimming pool surrounded by chaise lounges. The two-story house stands prominently in the background, with warm lights glowing from its windows. Umbrellas provide shade, and greenery enhances the tranquil ambiance.
Home in San Gimignano
5 out of 5 average rating, 19 reviews

"Vernaccia" by Podere la Fonte

Beautiful family-run country house, perfect for visiting the historical villages of the area such as San Gimignano, Volterra, Monteriggioni, and more. At Vernaccia of Podere la Fonte, you can discover the Tuscan countryside with all the necessary comforts for a relaxing and enjoyable vacation.

Guest favourite
A swimming pool is foregrounded with vibrant red roses, offering a striking contrast against the clear blue water. The panoramic view features rolling hills and the medieval towers of San Gimignano in the distance, with sun loungers arranged around the pool area.
Apartment in San Gimignano
4.95 out of 5 average rating, 139 reviews

Adalberto Apartment inside the Manor of Fulignano

Nella campagna di San Gimignano, in antica fortificazione risalente all'anno 1000 ora dimora di campagna, situata su di un colle con veduta panoramica, affittasi bellissimo appartamento di ca. 60mq con vista su San Gimignano e sui vigneti circostanti

Guest favourite
A spacious bedroom features warm wooden beams above and a large window allowing natural light to fill the space. A comfortable double bed is adorned with neutral-colored linens. An elegant armchair sits beside a small side table, complemented by a decorative rug on the polished wooden floor.
Flat in San Gimignano
4.91 out of 5 average rating, 23 reviews

Zafferano Rooftop Terrace Tower House

Zafferano is an elegant apartment set in the heart of San Gimignano, made unique by a perfect fusion of ancient and modern. Its panoramic top terrace will make you fall in love even more with the beautiful Tuscan hills and medieval towers.

Guest favourite
Apartment in San Gimignano
4.87 out of 5 average rating, 126 reviews

Scenic Stilish Country

Beautiful apartment nestled in the heart of the Tuscan countryside with a private garden and an amazing pool with unbeatable scenic views! Swimming pool open from 1 May to 30 September We look forward to welcoming you!

Popular amenities for Castel San Gimignano holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. Castel San Gimignano